Events in Winter Haven

Yoga-In-The-Flow w/ Glenys

Glenys leads a gentle flow yoga class created for beginners and anyone returning to movement. Expect an unhurried, supportive pace with breath-guided sequences that cultivate balance and deepen awareness of the body. No prior experience is needed. It offers a calm place to move and breathe, whether you want to ease tension and settle the mind or focus on building core strength. The practice meets you where you are and aims to nurture mind, body, and spirit. Cost is $15 per person and it is offered two times each month. Wear comfortable clothing, and bring a towel and a water bottle.

Grove Roots Brewing in Winter Haven

Enjoy tavern-inspired pizza prepared in small batches at Grove Roots Brewing Co. in Winter Haven.

Magic - Mid-Week Pauper

Settle in for a mid-week Magic Pauper tournament with a $10 entry fee. The event uses Swiss pairings with 50-minute rounds, and each match is played best two out of three. Earn one prize ticket for every match you win, and players finishing in the top four receive an extra ticket. Tickets can be traded for a selection of booster packs. The winner takes home a foil promo pack, and additional promo packs will be handed out at random.

Ed Sullivan

George Trullinger appears as Ed Sullivan, guiding a classic variety show experience filled with nostalgia and music. He hosts a powerhouse bill of award-winning tribute acts honoring Tina Turner, Mick Jagger, and The Blues Brothers. The performers capture the look, sound, and spirit of these icons with hit songs, signature moves, and high-energy stage presence. The result is a throwback television-style revue that celebrates beloved stars and the entertainment era they helped define.

Straight Outta Florida

A 90-minute mix of songs and sketches unfolds in the GhostLight Lounge as Compton & Bennett explore Florida’s quirks through a character-driven production. With two performers bringing six personalities to life, the story looks at the state from the inside using some of their most familiar creations. Earlene, a fifth-generation Floridian, sings about bogus swampland deals, rapid development, and the odd upsides of post-storm debris, accompanied by her pianist Gazpacho, cool and constant. Naomi Lipshitz-Yamamoto-Murphy cheerfully pursues husband number four while sidekick Ben Younger plays ragtime and fires off quick-witted lines. Florida Man, John Morgan, and the Skunk Ape also make appearances, rounding out a satirical tour that the tourism board might rather not advertise.

The Jam with No Name

Frankie hosts an open jam at Jessie's Lounge in downtown Winter Haven, welcoming musicians and music fans for a relaxed evening of creativity. Attendees can bring instruments, share a tune, or simply enjoy the live sets from the crowd. Players of any experience level are encouraged to take the stage, with the emphasis on energy, fun, and making music together. The bar is open with drinks to pair with the performances, creating a lively weekly gathering for performers and listeners alike.

Blueberry U-Pick

Enjoy a hands-on blueberry picking experience. Blueberries are priced at $5 per pound. Buckets are provided for picking, and bags are supplied for taking your harvest home.

Jukebox Bingo

Jukebox Bingo is a bingo-focused event where participants gather to play and enjoy the classic game.

AYCE Boneless Wings

Savor unlimited boneless wings, with a happy hour offered as well.

Pink Cherry Blossoms

Come and paint Pink Cherry Blossoms. Painters ages 15 and up may attend with a paid adult. You can also create your own long-lasting, all-natural scented soy candle before you paint. Enjoy a drink from the selection of wine, beer, or non-alcoholic beverages at the Bar. You may also bring your own snacks if youd like. Payment is required at the time of booking to reserve your seat.

Vendor Market

Kokomo’s Cafe hosts its debut vendor market, an evening of shopping with local vendors plus drinks and food available. Browse offerings from Bloome and Co., Emma Louise, MimosaMai Beauty, Central Charm Boutique, Olive Tree People, and StayFresh Stylez. Those interested in taking part as vendors at future markets can contact the organizers for more information.

Golden Age of Hollywood Awards Party

A Golden Age of Hollywood awards party unfolds with a live performance honoring Marilyn Monroe, then shifts into a cocktail hour and an awards ceremony that recognizes the night’s own golden stars.

Great Futures Celebration

This celebration honors the people who helped build Boys & Girls Clubs of Polk County and supports the programs that continue to change lives. Hosted at the George Jenkins Memorial Club, the evening features a tour of the Club, a silent auction, dinner, and a program that highlights the impact taking place in the Clubs each day. The program includes remarks from the 2026 Youth of the Year and offers insight into how caring, consistent programming and trusted mentors can shape a child’s future. The event also recognizes Walt Hall as the 2026 Great Futures Honoree, acknowledging decades of leadership that strengthened Boys & Girls Clubs of Polk County and empowered countless young people, establishing the Clubs as a foundation for growth, character, and opportunity.

Nitro Bingo

Nitro Bingo amps up the classic game with strobe lights, upbeat music, and a lively, social vibe. It suits groups, a girls’ night out, or anyone seeking an energetic midweek outing. Prizes add to the excitement, with a total of $1,350 up for grabs.

Commander B-I-N-G-O

Enjoy a casual commander event centered on a bingo-style challenge. Each participant receives a bingo card, then forms a group of three or more players to work through the listed tasks. Completing a line on the card earns a promo, and filling the entire card awards a second promo. The buy-in is the purchase of a booster pack of your choice.

Rodney’s Intuitive Circle

Rodney's Intuitive Circle offers a space for spiritual connection and personal growth. Participants explore intuitive communication with angels, spirit guides, and other divine energies, opening clearer channels to insight that can broaden perspective and reveal the bigger picture of one's life journey. The circle is open to beginners and those with experience in mediumship, encouraging breakthroughs and expanded awareness. The focus leans toward the intuitive side of mediumship, emphasizing work with angels, spirit guides, and related divine energies, while Misty's Mediumship Class centers on the paranormal side of the practice. Admission is $20 per person.

"You Are Loved" Ladies Night Out

This Ladies Night Out at First Baptist Church Lake Alfred in Lake Alfred, Florida centers on the uplifting theme You are Loved. The evening includes a performance by the Dove Award-winning group Triumphant. Tickets are available.

Camping World RV Expo

Explore special show pricing on a wide selection of new and used RVs at this expo at Camping World. See the latest models, take advantage of limited-time retail deals, and enjoy onsite activities. Attendees can also enter for a chance to win a new RV, with more to discover during the event.

Peace Train Karaoke

Peace Train Karaoke brings a sing-along night to Jessie’s Lounge, where karaoke fans can take the mic and perform their favorite songs. A playlist keeps the music flowing, and the drink selection complements the vibe. It is a chance to sing together in downtown Winter Haven.

Power Yoga @ Yoga Haven

This Power Yoga class is held at Yoga Haven and is presented by Radiant Roots Yoga. Registration is managed through Yoga Haven using a secure registration link.

AYCE Bone-In Wings

Treat yourself to unlimited traditional bone-in wings with an all-you-can-eat special. Bring a big appetite and enjoy as many as you like.

An Evening with Frank Foster

Join author Frank Foster for an evening of stories, laughs, and fly fishing tips. The event includes author remarks, a Q&A session, a meet and greet, and a book signing.

A Night of Legacy

Presented by the Polk State College Foundation with Citizens Bank & Trust, this signature black-tie celebration brings a premier formal evening to Polk State College. The night offers an elegant setting as attendees come together to celebrate.

Midnight Dragon - Thursday Book Club

Attend a painting instruction event where you can recreate a Midnight Dragon themed painting. An instructor will guide you through the process step by step. The event is open to painters ages 15 and up. Beverages including wine and beer are available for purchase, and you can bring your own snacks. Payment is required to reserve your spot.

Cocktails & Comedy @Lugo's Craft Distillery

Enjoy an interactive comedy show at Lugo's Craft Distillery Tours & Retail Store where admission is free. Audience members jot down topics or ideas, slip them into a bucket, and the comedians draw them at random to create stand-up in the moment. Lakeland Comedy brings Cocktails & Comedy with quick wit and spontaneity fueled by audience suggestions.

Live Music!!

Local musicians bring a blend of country, rock, folk, jazz, and acoustic music to Bowen Yard in Downtown Winter Haven. Settle into the outdoor setting, enjoy the atmosphere, and choose from five on-site restaurants while the performances unfold. Admission is free.

Magic - Final Friday Pauper

Compete in a Pauper Magic event with a $10 entry fee. Matches use a Swiss pairing structure and are best of three, with 50 minutes per round. Prize support is ticket based, awarding one ticket for each match win and an extra ticket for finishing in the top four, and tickets can be redeemed for various booster packs. The winner receives a foil promo pack, and additional promo packs will be given out at random.

Come Rock With Us

This event features a performance by a new rock band.

Blueberry Upick Today!

Enjoy a pick-your-own blueberry outing at the farm. Pricing is $5 per pound, with buckets supplied for picking and bags provided to carry your berries home.

Patriotic Wear Event

This event features a debut of patriotic-themed kids apparel. Browse clothing in red, white, and blue tones, with options suited to many occasions. Find pieces that celebrate a child's patriotic spirit and add stylish additions to a young wardrobe, with plenty of great finds throughout the event.

Fish Fry Friday

An all-day special on fish and chips is featured, with a happy hour offered later in the day.

Forever 55: FAB FRIDAY - April 24

For adults 55 and older, this gathering features a trivia session in the style of Jeopardy, hosted by Lisa of BrightStar Care. Participants may bring their own lunch, or contribute an appetizer or main course for a shared potluck.

2nd Annual Festival del Sanguich

Come to the 2nd Annual Festival del Sanguich during Hispanic Heritage Night at The Flying Tigers / Publix Field.

Swan Derby

Enjoy a day on the water with races, live music, food trucks, and a kids activity area. Show off your style in the Derby Hat Contest. The event supports Lakeland Volunteers in Medicine, and every moment helps provide healthcare to the medically underserved in the community. There is also a VIP Sponsor Reception inside the Magnolia Building that is an exclusive, ticketed event for sponsors, jockeys, and their guests and is not open to the public.

Bright Starry Night - Friday Blacklight

Enjoy step-by-step painting instruction from local artists. You will create a unique piece of art and have a great time. This event is for those ages 15 and up. You can purchase wine, beer, and non-alcoholic beverages at the bar. You are welcome to bring your own snacks. Payment is required at the time of booking to reserve your seat.

Magic - Secrets of Strixhaven Draft League

A Magic draft league centered on Secrets of Strixhaven offers structured play with three matches per event. Each match is scheduled for 55 minutes and played as best of three. A win earns one prize ticket, which can be exchanged for booster packs after the event. The league awards three points for attending an event and one point for each match victory, with bonus prizes available at 10 and 20 league points. The buy-in is $25 for each draft event.

Jim and Judy Live at Old Man Frank's

This event features Jim and Judy performing live at Old Man Frank's.

Free "Dinner & Movie"

This free monthly dinner and movie gathering welcomes families for an evening where a meal is served first, followed by a screening. To help with planning, attendees are asked to call the church office at (863) 439-1268 and share how many people will be coming.

Jaded

A live performance by Jaded takes place at Tanners Lakeside.

Open Mic Renegades

Open Mic Renegades returns to Kokomo's Cafe with an evening that showcases poets, singers, musicians, comedians, dancers, and more. All art forms are welcome, with two featured poets, live painting, and a marketplace of local vendors. There are 20 open mic slots available on a first come, first served basis, and performers sign up at the door. A $20 combo ticket includes admission, a food buffet, and one drink. Vendor participation is available for a $20 fee.

Ron Seggi Orchestra

Inspired by Dick Clark’s belief that music shapes our lives, this upbeat concert celebrates the soundtrack of multiple generations without relying on impersonators. Two-time Grammy nominee Ron Seggi leads his fifteen piece live Caravan of Stars orchestra with featured vocalists Tonya and Colecta for a night of audience participation, shared memories, and behind the scenes stories from a lifelong career in radio, television, and singing. Drawing on decades of interviews and collaborations with leading entertainers, Seggi and his supercharged band perform chart-topping favorites from the 1950s through the 1980s and beyond in a salute to his longtime friend Dick Clark and American Bandstand. The set highlights hits associated with Elvis, Roy Orbison, Neil Diamond, The Beatles, Ray Charles, Bobby Darin, Gene Pitney, Tina Turner, Huey Lewis, Tony Orlando, Frankie Valli, and Chuck Berry.

Blueberry Upick Today!

Enjoy a hands-on blueberry harvest at a u-pick event. Fruit is priced at $5 per pound. Buckets are available for picking, and bags are provided so you can take your berries home. For more information, check the farm's website.

Project E.A.G.L.E. 2026

This annual cleanup at Lake Shipp Park brings neighbors together to care for the Chain of Lakes and the wider Winter Haven area. Volunteers are welcome, and anyone under 18 must participate with a parent or authorized adult. Expect fun rewards, including prizes for the largest group, the most unusual find, and more. A free tree giveaway marks the Earth Day spirit. Registered volunteers receive lunch and cleanup supplies while quantities last.

Conspiracy Theory

Conspiracy Theory brings a high energy show to Caribbean Bay in Winter Haven, Florida, featuring a powerhouse set of hits from Journey, Led Zeppelin, Queen, Black Sabbath, Billy Idol, Poison, Tesla, Stone Temple Pilots, Aerosmith, Alice Cooper, Duran Duran, George Michael, Weezer, The Cranberries, Lover Boy, Michael Jackson, Godsmack, and more. Expect a lively mix of rock and pop favorites performed with plenty of punch.

Winter Haven Farmers Market

Discover a farmers market that brings together farmers, food trucks, and local makers. Shop for fresh produce, handmade pasta, baked goods, meat and seafood, and a selection of plants.

Hunter Fawcett Memorial Auto Show

The show will be held at Lions Park in Lake Alfred and is open to everyone.

Indie Bookstore Day

Celebrate Indie Bookstore Day with a focus on new stories and community. Explore fresh arrivals on the shelves, enjoy sweet treats from Enchanted Bites, and take part in giveaways while you browse. Every purchase supports a small business and the dream behind it.

Community Cleanup Day

Community Cleanup Day welcomes volunteers of all ages to gather at City Hall, pick up litter pickers, garbage bags, and vests, and head out to clean up around town. Lunch is provided at City Hall.

20th Annual Jump-Off: Scholarship & Success Brunch

Now in its 20th year, the HBCU Jump-Off at Denison Middle School features the Scholarship and Success Brunch, a no-cost event focused on college readiness. It is open to high school students, and registration is currently available.

2nd Annual: The Women’s Wellness Experience by LPA

This is a free community event focusing on womens mental health, mindfulness, and holistic well-being. Women from all backgrounds are invited to reconnect and recharge through movement, conversation, and community care. Activities include yoga and Pilates sessions, a mini sound bath, and talks by speakers sharing insights on women’s mental and emotional wellness. There will also be hands-on activities, wellness vendors, raffles, giveaways, and community networking. Attendees are encouraged to bring period products to donate to Polk Period Pantry.

Petting Zoo

A petting zoo from Gamble Family Farm gives children a chance to meet friendly farm animals. Entry for each child is $3 for access to the petting area, and animal feed can be purchased for $2 per carton.

Spring into Summer Sale

Celebrate seasonal savings at the Spring into Summer Sale Event with discounts up to 50 percent. Enjoy refreshments and take part in a drawing for a chance to win a $100 gift certificate.

Chain of Lakes Cycling Classic

This two day cycling event in Winter Haven marks its 17th year in 2026, continuing its mission to bring premier bike racing to Polk County. The road race takes place in the Lake Buffum area east of Fort Meade. On Sunday, racing shifts to Florida Polytechnic University for the second day of competition.

City-to-City: It's Showtime - Artist Music Showcase

This live showcase brings R&B, hip hop, and reggae to the stage at KULTURE on 1st. Performers can take the mic, connect with other artists, and compete for the spotlight in a music-centered gathering.

Saturday Markets

Presented by Winter Haven Saturday Market, Winter Haven Saturday Markets is an event in Winter Haven, Florida.

PJ’s BBQ Food Truck

Spend a spring Saturday with PJ’s BBQ Food Truck offering barbecue, fresh juice available in the market, and ice cream. Pick your own sunflowers and settle into the rocking chairs while the kids play.

Tarot Round Circle

Explore the layers of tarot by delving into imagery, elemental influences, and energetic themes that shape each card’s story. The class centers on reading beyond the obvious to find deeper meaning in every draw. It welcomes newcomers as well as seasoned readers, with takeaways for all experience levels. Admission is $7 per person. Please bring a Rider Waite deck.

Spring Time Tulips

Enjoy a painting class where you can create a picture of Spring Time Tulips. This event is open to anyone 15 years or older; painters ages 15+ may attend with a paid adult. You can also make your own scented soy candle before you paint for an additional fee. If you choose to make a candle, please arrive 30 minutes early. You can enjoy a drink from their selection of wine, beer, or non-alcoholic beverages at their bar, and you may also bring your own snacks.

A Galactic Love -BlackLight

Enjoy a night of painting, suitable for ages 15 and up, where you can create your own unique piece of art. You can also create a candle for an additional charge. Beverages including wine, beer, and non-alcoholic drinks are available for purchase, and snacks are welcome. Please arrive promptly; instruction begins on time. Payment is required to reserve your spot.

Yu-Gi-Oh: Rarity Collection 5 Release Event

Celebrate the release of Rarity Collection 5 with an Advanced Format tournament. Entry is the purchase of three Rarity Collection 5 booster packs. Matches follow a Swiss pairing structure, are best of three, and run 50 minutes each. Prize support awards one OTS pack for every match win, one OTS pack to each of the top four finishers, and a playmat for first place.

Woman’s Circle

This circle brings women together with Alana for an informative, supportive gathering centered on personal growth and purpose. Drawing on her experience in helping women reach their full potential and clarify their purpose, Alana facilitates conversation and connection. Participants can form new friendships and a family-like bond, work through challenging aspects of womanhood, and celebrate its best moments. The event is free to attend.

Blueberry Upick Today!

Pick fresh blueberries straight from the bushes at a u-pick outing. Pricing is $5 per pound. Buckets are supplied for picking, and bags are provided to carry your berries home.

Taco Riendo Food Truck

At Golden Ridge, enjoy tacos from Taco Riendo for lunch, sit on the porch with ice cream while kids play on the lawn, and wander the Sunflower Fields to pick sunflowers to take home.

Happy Sunflowers

Unleash your inner artist at a painting event suitable for ages 15 and up, where participants can enjoy step-by-step guidance from experienced local artists to create their own unique masterpiece. You can also create your own scented soy candle before you paint. This public event welcomes those 18 and older, while painters ages 15+ can join in with a paid adult. A selection of wine, beer, and non-alcoholic beverages are available for purchase at the bar for those 21 and over with valid ID. Participants are welcome to bring their own snacks, and seating arrangements can be requested during registration to ensure friends can sit together.

Lorcana - Core Constructed

Take part in a Lorcana Core Constructed tournament with a $10 buy in. Matches are played in 50 minute Swiss rounds, best two of three, with the total number of rounds based on turnout and capped at three. Prizes include one booster pack for each match win, plus a pack for anyone who finishes without a match win. The top four receive promo cards, and two additional promos will be awarded by a roll of a big d20.

Trivia with Ron @ Raise the Bar and Grill

This event features three ten-question trivia games, with prizes awarded after each one. Attendees should plan to purchase food and drinks and bring a pen or pencil for writing answers. Bring your best brainpower for a chance to leave a winner.

Las Rosas Colombian Cuisine Pop-Up

Enjoy Colombian American Fusion food and street fare as they serve the city of Lakeland.

AARP Smart Driver™: Winter Haven Senior Center

An AARP Smart Driver course takes place at the Winter Haven Senior Adult Center. Participants must attend both sessions and should either pay online in advance or bring a check made payable to AARP. The fee is $20 for AARP members and $25 for nonmembers. Please remember to bring a driver’s license.

Kid's Eat FREE

This promotion features complimentary meals for children when an adult meal is purchased. A happy hour is also available.

Yikes! What's Happening to My Body? BOYS EDITION

An informative session for ages 9 to 12 that explores the bodily, cognitive, and emotional changes that come with the transition to adolescence. The program focuses on what children can expect as they get closer to their teen years.

Main Character Energy: Diva Night

Enjoy a painting and wine party! You can create your own long-lasting, all-natural scented soy candle before you paint. This event is open to painters 15 years or older, but those under 18 must be accompanied by a paid adult. Instruction begins promptly at the start time. You can enjoy a drink from the bars selection of wine, beer, or non-alcoholic beverages, and you may also bring your own snacks.

Polk State Student Art Exhibit Reception

Polk State is presenting the annual reception for its Student Art Exhibition at the Winter Haven Fine Arts Gallery. Admission is free. The exhibit remains on display and is open to the public.

Pokemon League Challenge - April 2026

Take part in a monthly Pokemon League Challenge featuring Standard Format play with best of one rounds. Registration is required by phone at 863-324-1323, and participation is limited to 16 players, so securing a spot in advance is necessary. Expect three to four rounds based on turnout. Entry is $5. Bring a completed decklist to check-in that includes your first and last name, Pokemon ID number, date of birth, and the exact counts and versions of every card in your deck. Matches begin promptly, and players who arrive late or do not submit a completed decklist before the first round will not be able to participate. Prize support includes one prize pack for each match win, an extra pack for the top four finishers, and a pack for every participant.

Tribute to Aerosmith and more

At The Ritz Theatre, a double bill salutes the music of Aerosmith and Loverboy. Aerosmith Rocks! delivers the band’s arena-sized punch with soaring vocals, fiery guitar work, and stagecraft that recalls Steven Tyler’s signature moves. Expect classics like Walk This Way, Dream On, and Sweet Emotion alongside deeper tracks, all played with tight precision. Get Lucky follows with a lively tribute to Loverboy, rolling through Working for the Weekend, The Kid Is Hot Tonight, and more signature hits. Sharp harmonies, propulsive rhythms, and an unmistakable 80s spark keep the energy high from start to finish.

Aerosmith Rocks! and more

Aerosmith Rocks! channels the band’s bad-boy swagger with gritty attitude, soaring vocals, scorching guitar work, and the unmistakable frontman strut that recalls a full throttle Aerosmith concert. Get Lucky follows with a high energy salute to Loverboy, serving up favorites like Working for the Weekend and The Kid Is Hot Tonight while capturing the upbeat spirit of the 80s. Built for rock fans of all ages, it is pure feel good, fun loving rock and roll.

Polk State Music Spring Choir Concert

Polk State Music presents a Spring Choir Concert at the Polk State Winter Haven Fine Arts Theatre. General admission costs $10. Students with school IDs and Polk State faculty and staff with College IDs can attend for free.

Trivia Night

Trivia night offers a friendly question-and-answer challenge.

OneBlood Blood Drive

Give blood at the OneBlood drive hosted at Oak Ridge Funeral Care - Winter Haven. Donors receive a $20 eGift card, an umbrella, and a wellness checkup that includes blood pressure, pulse, temperature, iron, and cholesterol screening. Appointments are encouraged to reserve a spot. A valid ID is required. The donor offer is limited to one per donor per donation, has no cash value, is not transferable, and items may vary while supplies last.

Ribbon Cutting: Miller's Central Air

Celebrate the grand opening of Miller’s Central Air’s second location in Winter Haven. For more than three decades, the company has delivered expert air conditioning, heating, and HVAC services. Drawing on deep experience with Florida’s climate, coastal environments, seasonal humidity, and intense heat, the team offers practical insight into how local HVAC systems perform, age, and adapt to environmental changes. RSVP to Lynn by email.

Taco Tuesday

Three tacos served with fries or chips and salsa are available for $8.99. A happy hour is offered as well.

Free Educational Seminar on Estate Planning

Attend a complimentary event hosted by the National Association of Family Services and discover how to help your family leave a legacy. Learn how to organize your affairs and secure your estate and financial needs.

Wine Tasting

Join in for an evening where you can enjoy some wines with a charcuterie board. Its a chance to unwind, taste new flavors, and enjoy great company. Do not miss out on this experience!

Neon Mountain Sunset: Blacklight

This event is for ages 15 and up. You can create your own long-lasting, all-natural scented soy candle before you paint. If you choose to make a candle, please arrive no later than 30 minutes prior to the event. Enjoy a drink from the bar’s selection of wine, beer, or non-alcoholic beverages. You may also bring your own snacks.

Free Bingo

Enjoy a free bingo night at Bowen Yard in Downtown Winter Haven. Share the fun with friends, enjoy food from five restaurants, and play for prizes.

Magic - Mid-Week Pauper

Take part in a Magic Pauper tournament with a $10 entry fee. Matches are played as best of three in 50 minute Swiss rounds. Earn one prize ticket for each match win, plus an extra ticket for finishing in the top four, and redeem tickets for different booster packs. First place receives a foil promo pack, and additional promo packs will be awarded at random.

Blueberry Upick Today!

Harvest fresh blueberries at a u-pick event. Berries are priced at $5 per pound. Buckets are available for picking, and bags are provided for taking your blueberries home.

Jukebox Bingo

Jukebox Bingo offers a chance to play bingo.

AYCE Boneless Wings

All-you-can-eat boneless wings are available, with a happy hour also offered.

Starlit Crescent - Book Club

Enjoy a painting event for ages 15 and up. An instructor will guide you in creating your own art. Drinks including wine and beer are available for purchase, and you can bring your own snacks. It is required to arrive by the designated start time or 30 minutes early if making a candle. If you want to sit with friends, all guests must enter the same group name when registering. You can also create your own scented soy candle before you paint, just look for the DIY CANDLE add-on during registration.

Winter Haven Middle School Classic

This middle school classic takes place in Winter Haven, Florida and is featured on MileSplit with an official meet page.

Ribbon Cutting: Winter Haven Recreation and Cultural Center

A ribbon cutting with the City Commission will mark the official opening of the new Winter Haven Recreation and Cultural Center. An open house with tours follows, providing a chance to see the facility. This $21 million investment, shaped through extensive community input and collaboration, represents a meaningful milestone for the community.

Two-Headed Giant Commander B-I-N-G-O

Players team up with a friend for a laid-back Two-Headed Giant Commander event with a B-I-N-G-O twist. Each participant receives a bingo card on arrival. Players form groups of three or more and aim to complete the tasks listed on their cards. Finishing a row earns a promo, and filling the entire card awards a promo pack. Entry is the purchase of a booster pack of your choice. Participation promos are available for all players. Two-Headed Giant Commander rules are in effect.

Nitro Bingo

Nitro Bingo turns a familiar pastime into a high-energy night with flashing light effects, lively music, and a friendly, social vibe. It suits groups, a friends’ night out, or anyone seeking an exciting midweek break. Look for a total prize pool of $1,350 and an atmosphere that keeps the energy high from start to finish.

Everyday Magic w/ Alex.

Returning by popular demand, this class with Alex focuses on practical ways to weave magical practice into daily life, helping connect the inner self with the outer world. After more than a year away from Moon Dreamz, Alex brings back a session that works well for newcomers and for anyone seeking a refresher. The class is $20 per person. Before the session, Alex will be available for in-house readings, offering a chance to meet with him ahead of time.

Peace Train Karaoke

Peace Train Karaoke brings a karaoke night to Jessie's Lounge, where attendees can sing favorite tunes, move with the playlist, and choose from a fitting drink selection. Set in downtown Winter Haven, it is centered on stepping to the mic and sharing the music.

AYCE Bone-In Wings

Unlimited classic bone-in wings are offered, and a happy hour is available.

Sassy Henrietta

Enjoy a painting session to create your own version of Sassy Henrietta. This event is for ages 15 and up. You can purchase wine, beer, and non-alcoholic beverages. You may also bring your own snacks. Arrive 15–20 minutes early to check in and get settled. Instruction starts promptly on time.

First Friday Free Bites!

First Fridays get underway at Bowen Yard with complimentary samples from the restaurants at the venue. Stop by to taste a few bites and get a feel for the dining options available there.

First Friday Winter Haven

First Friday is a monthly evening in downtown Winter Haven filled with dining, drinks, and shopping. Visitors will find specials at local bars and restaurants, explore downtown businesses that stay open later for the occasion, and enjoy live music along with other entertainment at several locations. The festivities also feature the First Friday Car Show and the First Friday Night Market.

First Friday Market

The Winter Haven Night Market offers a family friendly evening with a car show, local vendors, and Zesty Bubbles serving dirty soda and dirty popcorn. Attendees can enjoy a welcoming atmosphere with eye catching cars and chances to browse and shop from local sellers.

Live & Loud

Live & Loud brings Polk County a monthly jolt of homegrown sound at the Historic Ritz Theatre. This series elevates rising artists and creatives from the local scene, offering a welcoming, inclusive setting where they can push boundaries, claim the stage, and make plenty of noise. This edition spotlights Lyche Camp from Tampa, Colorblind Dinosaurs from Mount Dora, and Defrauded from Tampa. Presented in partnership with Punk Kid Productions LLC.

Magic - Standard Showdown

This Magic Standard event features three Swiss rounds, each 50 minutes and played best of three. Earn one prize ticket for each match win, with an extra ticket awarded to players who finish in the top four. Tickets can be redeemed for assorted booster packs. First place receives a foil promo pack along with an additional promo card. Extra promo packs will also be distributed at random. The buy in is $10.

May First Friday - Sip & Glaze

Enjoy a relaxed, creative evening as AS Ceramics teams up with Union Taproom for a First Friday edition of Sip & Glaze. No experience is necessary. Each ticket includes a handmade ceramic incense burner crafted by local artist Austin Snedden, a full range of professional glazes with all the brushes and tools, and on-site guidance to help you customize your piece. After you finish glazing, the burner will be taken to the studio for kiln firing and will be available for pickup at a later time. All ages are welcome. Union Taproom in Winter Haven features a pour-your-own selection of craft beers, wines, and ciders that sets an easygoing atmosphere for making art. Tickets are $40 per person, and capacity is limited, so early purchase is encouraged.

Live and Loud

Live & Loud brings Polk County a monthly surge of underground sound and emerging talent in an inclusive, welcoming setting where up-and-coming artists push limits and take the spotlight. Each installment is built for discovering fresh bands from the region. This edition spotlights Defrauded, Lychee Camp, and Grim Gardener from Tampa, alongside Colorblind Dinosaurs from Mount Dora.

Conspiracy Theory Rocks La’s Midway!

Conspiracy Theory returns to La’s Midway Saloon with a high‑voltage set celebrating rock and pop across the decades. The show rolls through signature anthems and fan favorites by Journey, Led Zeppelin, Black Sabbath, Billy Idol, Poison, Tesla, Stone Temple Pilots, Aerosmith, Alice Cooper, Duran Duran, George Michael, Weezer, Korn, Godsmack, and more, creating a lively soundtrack for a full night at the saloon.

99 in the Shade @ Somewhere Sports Bar & Grill!

An evening of dancing unfolds at Somehwre Sports Bar and Grill, with food and drinks available and staff on hand throughout the night.

Blueberry Upick Today!

Enjoy a u-pick blueberry experience at the farm, with pricing at $5 per pound. Buckets are provided for picking and bags are available to take your berries home.

Fish Fry Friday

Enjoy fish and chips offered as a special, along with a happy hour.

You Name It!

A comedic performance spotlights Charlie, who presents herself as a woman of many trades, offering everything from medical help and tax fixes to ticket hookups. Whatever you need, she says you only have to name it. In truth, her friendly facade hides a skilled scammer.

Free Comic Book Day

This one day giveaway offers complimentary comics. Each person may choose up to five different issues from the designated free comic tables, and holds are not available.

Magic - Secrets of Strixhaven Draft League

This Magic draft league features three 55 minute rounds, each played best of three. Players earn one prize ticket for every match win and can redeem tickets for booster packs after each event. League scoring awards three points per event attended and one point per match win, with bonus prizes at 10 and 20 points. The buy-in is $25 per draft event.

Are You Ready To Get Twizted?

Caribbean Bay hosts a rock and roll celebration with a Twizted twist, bringing lively party energy and upbeat vibes.

Bobby James

Bobby James returns to Florida with a stop at Twisted Prop, performing songs from his current album Madison alongside covers that have influenced his music.

Blueberry Upick Today!

Pick your own blueberries at the farm. The price is $5 per pound. Buckets are supplied for picking, and bags are provided so you can take your berries home.

Cardboard Boat Race

Celebrate local lakes, rivers, and the underground drinking water supply at a community festival featuring a team cardboard boat race that spotlights creativity and problem solving from residents, businesses, community groups, and youth organizations. Teams craft a boat primarily from cardboard and duct tape, then send two pilots to paddle a course that begins on the beach, circles the ski jump, and returns to shore. Trophies and prizes are offered in two divisions, adult for ages 18 and up and youth for under 18, with special honors that include the Swift Dinghy Award for the fastest finish, the Gene Leedy Award for most creative design, and the Titanic Award for the most spectacular sinking. Family and friend teams are welcome and no official affiliation is required. A $25 entry fee and signed liability waiver are required to compete. Each team must field two pilots, while any number of additional helpers may assist with design and construction. Adults may help youth teams build, but both pilots must be under 18 to compete in the youth division. Space is limited to ten teams per age category and registration is first come, first served. Pilots must wear a Type 1, 2, or 3 personal flotation device. Teams are encouraged to bring their own PFDs, and a limited number may be available from event staff if requested in advance. Boats and paddles must be built by each team and made primarily of cardboard. Materials such as rubber, foam, inflatables, and wood may not be used to enhance buoyancy. Duct tape, glue, and contact cement are acceptable adhesives, but waterproof coatings on the underside of boats are not allowed, and motorized propulsion is prohibited. One week before the festival, each team receives a construction kit with four sheets of 4-by-8-foot cardboard, three rolls of duct tape, a ruler, a utility knife, and two pencils. Teams may purchase additional materials for building or decorating, and designs should avoid offensive, political, or inflammatory themes. Event staff may disqualify teams that break the rules, which can include forfeiting the entry fee and potential bans from future events.

Winter Haven Farmers Market

Explore a lively farmers market featuring farmers, food trucks, and local makers. Pick up fresh produce, handmade pasta, baked goods, meats and seafood, and a variety of plants while you browse the vendors.

7 Rivers Water Festival

The 7 Rivers Water Festival is a community celebration of shared water resources in the Polk County region, marking more than a decade of dedication to protecting them. Attendees can explore vendor booths, watch a cardboard boat race, and enjoy a performance by the Cypress Gardens Water Ski team. Presented in collaboration with the City of Winter Haven, Polk County, and the City of Lakeland, the festival promotes understanding, appreciation, and stewardship of lakes, rivers, and the underground drinking water supply.

Lounge Lyzrds at La's Midway Saloon - 5/2/26

After some time away, Lounge Lyzrds return to La's Midway Saloon in Lake Albert, ready to bring their Lyzrd-style party back to a familiar stage.

Annual Spring Tack Sale

Browse a seasonal tack sale with fill-a-bag specials and buy one, get one promotions on both new and used tack. Stock up while supporting feed and hay expenses, as all proceeds are dedicated to that purpose.

Watermelon Day

This annual celebration features free admission and a variety of watermelon themed activities.

31st Annual Heritage Day Festival

The 31st Annual Heritage Day Festival is a free community gathering that celebrates legacy, unity, and culture. Expect live entertainment, a colorful fashion showcase, a variety of food vendors, an auto show, and activities for children. Complimentary health screenings will be available, and the program features a tribute to historic churches in Polk County.

Bandit Market Summer Party

Back for its tenth edition, Bandit Market brings a sunny celebration of makers and finders. Explore vendors from across central Florida featuring vintage treasures, art, handcrafted wares, baked goods, and more. Vendor applications are open.

Mom's In Love with Sunflowers

Spring Has Sprung

Paint Spring Has Sprung at a painting and wine party. Painters ages 15 and up are welcome to attend with a paid adult. Those making a candle should arrive 30 minutes early. Enjoy a selection of wine, beer, or non-alcoholic beverages from the bar. You may also bring your own snacks. Payment is required at the time of booking to reserve your seat. Located in High Pointe Plaza, behind Citizens Bank.

Yu-Gi-Oh - Blazing Dominion Premiere Event

Entry requires purchasing five or more Blazing Dominion Booster Packs. Play follows the Advanced format, and Blazing Dominion cards are legal. The event runs for three to four Swiss rounds, with matches decided in a best of three. Prize support includes OTS packs, additional Blazing Dominion Booster Packs, and special promo items for first place and for one randomly selected player.

Blueberry Upick Today!

Enjoy a u-pick blueberry experience at the farm. Pricing is $5 per pound, and buckets for picking along with take-home bags are provided.

Mother's Day Brunch

A brunch gathering dedicated to honoring mothers and the mother figures who enrich our lives. It offers a thoughtful occasion to express appreciation and gratitude for their care and support.

B.Haven Band

B.Haven Band will be performing.

Flowers for Mom

Enjoy a painting and wine party. With step-by-step guidance from experienced local artists, you can create a unique piece of art. You can also create your own scented soy candle before you paint if you arrive 30 minutes early. There is an additional charge for the candle option. This event is open to painters ages 15 and up with a paid adult. Those 18 and over are welcome to attend on their own. Guests can purchase wine, beer, or non-alcoholic beverages at the bar. You may also bring your own snacks.

Brunch on 1st

Experience a daytime hangout with a great vibe. Book your seat for Brunch on 1st, it promises to be fun!

FREE Skin Cancer Screening

Winter Haven Women's Hospital is offering free skin cancer screenings in recognition of Melanoma Monday. The checks are quick and comfortable. Adults age 18 and older are eligible. Wear loose clothing to make the screening easier. Walk-ins are accepted as availability allows.

Tacos and Tequila: Cinco de Mayo

Enjoy a painting activity with step-by-step guidance from experienced local artists. Attendees can purchase wine, beer, and non-alcoholic drinks. Painters ages 15+ may attend with a paid adult. Optionally, you can create your own scented soy candle before you paint, but you should arrive 30 minutes early if you choose to make a candle.

Blueberry Upick Today!

This u-pick blueberry event features fresh berries you can harvest yourself for $5 per pound. Buckets are provided for picking, and bags are available for taking your berries home.

2026 "She Knows Where She's Going" Luncheon

At Historic Ritz Theatre, Inc, the 2026 She Knows Where She's Going Luncheon honors four women whose dedication and contributions have benefited the Greater Winter Haven community. This luncheon offers a warm celebration of their service and local impact.

Magic - Secrets of Strixhaven Commander Bingo Party

Casual Commander play meets bingo with Secrets of Strixhaven themed twists. Each participant receives a bingo card at the start, then forms a group of three or more players to work on the tasks listed on the card during games. Finish any line to claim a promo, and complete the entire card to receive a promo pack. Participation promos are provided to all players. Entry requires purchasing a booster pack of your choice.

Conversations in Behavioral Health: Building a Mindful Community

Mental health touches families, workplaces, classrooms, and neighborhoods across Polk County, yet important dialogue often begins only after a crisis. This summit was created to shift that pattern by fostering proactive, meaningful conversations. Now in its third year, it brings together professionals, community leaders, educators, healthcare providers, and residents who share a commitment to strengthening mental and behavioral health locally. The one day program features three keynote talks that blend insight with lived experience, eight breakout sessions focused on practical strategies, emerging topics, and community solutions, and a hub of local behavioral health organizations offering resources and support. Throughout the event, participants engage in open, honest discussions that build understanding, reduce stigma, and provide tools that can be used at home, at work, and in schools. Attendees leave with deeper knowledge, stronger connections, and a clearer path to creating healthier, more supportive environments across Polk County. It is designed for behavioral health and healthcare practitioners, educators and youth advocates, nonprofit and community leaders, law enforcement and first responders, employers and HR professionals, faith leaders and ministry teams, parents, caregivers, and community members who value mental wellness. Registration is free, although space is limited.

2nd Friday night meet up

This free event is open to all. All makes, models, and years are welcome to show off their rides.

Tribute to Pink Floyd

A celebration of Pink Floyd takes the stage at The Ritz, featuring music from Dark Side of the Moon, The Wall, A Momentary Lapse of Reason, and Wish You Were Here. Classic Rock Legacy leads the performance with a roster of award-winning musicians whose past collaborations include Sting and Godsmack. An immersive light and laser show accompanies the music.

Blueberry Upick Today!

Enjoy a pick-your-own blueberry outing at the farm. Pricing is $5 per pound. Buckets are supplied for harvesting, and bags are provided so you can carry your berries home.

Almost There

Almost There brings an outdoor show to the parking lot at Somewhere Sports Bar in Winter Haven. The set spans rock, metal, alternative, pop, and classics, with the possibility of a few new songs requested by friends. Expect a lively night with drinks and live music.

Blueberry Upick Today!

Enjoy a hands-on blueberry picking experience. The price is $5 per pound. Buckets are available for picking, and take-home bags are provided.

The Highway 41

The Highway 41 Band, a country group from Central Florida, returns to Out-n-About Bar and Music Lounge for an evening of country music.

Winter Haven Saturday Markets

This event takes place in Winter Haven, Florida and is organized by Winter Haven Saturday Market.

A Mother's Heart -

Pure Shores

Enjoy a guided painting session suitable for ages 15 and up, led by instructor Valentina. Guests can purchase wine, beer, or non-alcoholic beverages, and are welcome to bring their own snacks. Arrive early if youd like to make your own all-natural scented soy candle.

2026 AAU Tangerine Tango Grand Prix

The 2026 AAU Tangerine Tango Grand Prix will feature over 90 volleyball teams competing. Admission is charged per day, with weekend passes available. Spectators can watch from the upstairs viewing area, and are welcome to bring chairs as seating is limited. Enjoy vendors, food trucks, a food drive, giveaways and themed days. Wear Christmas attire on the first day and floral prints on the second.

Little Birdies

Every Saturday, the community is invited to a vibrant market featuring locally-grown produce, fresh pasta, baked goods, juices, meats, seafood, plants, and unique creations from local makers. This week, The Little Birdies will perform their Appalachian-style bluegrass.

Lorcana: Wilds Unknown Prerelease (Sealed)

This event marks the first Lorcana prerelease to use the new Prerelease Kits. It runs as a sealed deck tournament with three Swiss rounds, best of one, at 30 minutes per round. Prize support includes one booster pack for each match win, and any player without a match win still receives a pack. Additional boosters will be given out at random based on the roll of a big d20. Entry is $50.

Arabellas Pre-Show Dinner Special

Turn Tribute Tuesday into an Italian evening with a pre-show four-course dinner in Winter Haven. Begin with an antipasto such as burrata caprese, mozzarella in carrozza, or fiocchi al gorgonzola, followed by a fresh house salad. For the main course, choose from salmon with a honey dijon glaze, NY strip tagliata di manzo, fettuccini alfredo, house lasagna, or chicken or veal prepared piccata, parmigiana, or marsala style. A chef-selected dessert completes the meal. Vegetarian selections are available, and most allergies can be accommodated. Substitutions are not offered, and beverages, alcoholic drinks, and gratuity are not included.

1 Million Cups

A free, weekly gathering where local founders showcase their ventures and receive immediate feedback over coffee. Each session features two entrepreneurs delivering pitches and hearing reactions from the group.

Magic Commander Bingo

Magic Commander gets a bingo twist in this casual event. Participants receive a bingo card on arrival, then form groups of three or more to work through the tasks on their cards. Completing any line earns a promo, and filling the entire card earns a second promo. The buy-in is a booster pack purchase of your choice.

A Cottage View

Enjoy a painting session to create "A Cottage View." Painters ages 15 and up are welcome to attend with a paid adult. You can also create your own scented soy candle before the painting session, please arrive 30 minutes early if you choose to make a candle. Enjoy a drink from the selection of wine, beer, or non-alcoholic beverages at the bar. You may also bring your own snacks.

Winter Haven VFW

The Summit Kings perform at Vfw Post 4289 with a mix of classic rock and energetic blues tailored for both dancing and listening.

Twizted Times Call For Twizted Measures

A lively evening built around music, a Cuban sandwich with a twist, and a cold brew by the lakeside. The atmosphere leans easygoing, pairing simple flavors with a soundtrack that keeps the good times rolling.

Riftbound - Nexus Nights

Riftbound - Nexus Nights features a 1v1 Constructed format with three 50 minute Swiss rounds played as best of three. Prize support includes one booster pack for each match win, a booster pack for anyone who finishes without a match win, and an extra pack for the top four. Entry is $10.

B.Haven Band

B.Haven Band will be performing.

Wicked Moonlight

Daniel Pepin live at Grove Roots

Daniel Pepin takes the stage at Grove Roots for a live performance that brings a night of music and more.

Golfing for Glory

Golfing for Glory is a charity golf tournament at Cypresswood Golf & Country Club, hosted by Veterans Outdoor Ministries to support faith-based outdoor programs for veterans. The competition follows a four-person scramble format and brings together players, sponsors, and supporters for a day centered on friendly competition, fellowship, and purpose. Early bird pricing is available for a limited time, with individual entry set at $100 and a four-person team priced at $400.

Veterans Outdoor Ministries 1st Annual Golfing Charity Event, CYPRESSWOOD GOLF & COUNTRY CLUB

This first annual charity golf event at Cypresswood Golf & Country Club supports Knights of Columbus St. Mary Council 4444 and fills the course with contests and standout prizes. The KRANK It Hole gives every golfer a chance to win a swing speed specific Formula KRANK driver valued at $700, and a long drive competition will be held with Open and Seniors or Women divisions. A featured Hero Hole offers a $1,000 hole in one prize plus closest to the pin awards for first and second. Two hit the green challenges raise the stakes, with one offering a chance at up to $50,000 and another featuring a $2,800 Cancun five day, four night stay. Both challenge holes also come with a shot at $5,000 dual stays through the "The World Is Yours" travel prize, and rare collector’s edition Hero Drivers may be available. For details, contact Justin at 570-484-1863.

The Good, The Bad, and The Twizted

Twizted returns to LA's Midway Saloon for a rock and roll show.

Winter Haven Farmers Market

The market showcases local farmers, food trucks, and makers. Offerings include fresh produce, handmade pasta, baked goods, meats, seafood, and plants, plus items crafted by local artisans.

SOLD OUT — 🔥 JERK & JAM FESTIVAL

Food lovers and market browsers can find plenty to enjoy at the Saturday Shoppes Jerk & Jam Festival, from big, flavorful bites to distinctive handcrafted goods. Located in Lakeland, this lively gathering offers a Saturday outing with tastes and makers all in one place.

Scenic Maui - Sunset

This event is open to painters ages 15 and up, and those under 18 must be accompanied by a paid adult. During the class, you can purchase wine, beer, and non-alcoholic beverages. You are welcome to bring your own snacks. If you would like to make your own scented soy candle, you may do so for an additional fee, but you must arrive 30 minutes early.

Jessica Michelle Singleton

See Jessica Michelle Singleton perform live.

WE ARE HERE TO PARTY WITH YOU !!!

A lakeside party offers drinks, great food, and time with friends. Rock and roll from the 70s, 80s, and 90s sets the vibe, and there may be surprises along the way. A love of a good challenge keeps the energy high.

Walter Parks

Gram Parsons Derry Down hosts a night with Walter Parks, a guitarist, singer, and songwriter whose original work and tributes are steeped in the sounds and stories of the Okefenokee Swamp, the headwaters of the Suwannee River near his North Florida roots. His research and imaginative reinterpretations of hollers, hymns, and reels from swamp homesteaders are preserved in the American Folklife Collection at the Library of Congress. For ten years he toured and recorded worldwide with Woodstock icon Richie Havens, performing at venues such as Carnegie Hall and Madison Square Garden, as well as the Glastonbury Festival in England. In 2014 he served as Judy Collins’s sole accompanist at her Lincoln Center tribute to Pete Seeger. Parks also leads two Americana-rooted ensembles, Swamp Cabbage (electric folk rock) and The Unlawful Assembly (reimagined spirituals). Now based in St. Louis, he co-produces The Concert at The Burroak with his wife, Margo. Admired by artists like JJ Grey, Judy Collins, and Rockwood Music Hall’s Ken Rockwood, he is celebrated for a voice and guitar style that can be both tender and thunderous. Expect an intimate evening of swamp-sourced tradition, modern grit, and soulful storytelling.

A Day in the Life

A Hidden Gem

Try something new and create your own long-lasting, all-natural scented soy candle before you paint! Look for the DIY CANDLE add-on option during your event registration. Arrive a little early to get settled. If you’re coming with others, give the group’s name in the Special Request box and the venue will seat you together. You are welcome to bring your favorite bottle of wine or beer and other food or snacks. The venue provides cups and cork screws. These classes are intended for adult painters, although painters aged 15 to 20 are permitted with the understanding that you must be at least 21 to consume alcohol in the studio. Younger painters can participate in Family Classes and Kids Classes.

Samantha Fish and more

Samantha Fish delivers thrilling live entertainment, turning a night out with friends or a long-awaited plan into something special. Tickets are available as long as seats remain.

Gnarly Quinn: Kevin's B-Day Bash @ LA's!

Gnarly Quinn travels to LA's for a birthday bash honoring drummer Kevin. This celebration keeps the focus on marking his big day with the band at the venue.

Island View - Set - DATE NIGHT- BLACK LIGHT

Carry Me Back Rock N Roll!

A Twizted good time awaits as this rock and roll night returns to Out-n-About Bar and Music Lounge.

La Midway Presents X it 7 Live

Presented by La Midway, this live performance features X it 7 sharing brand new songs with the audience. The artists express enthusiasm about seeing everyone and offer a warm message of appreciation.

Winter Haven Saturday Markets

This Saturday market takes place in Winter Haven, Florida and is organized by Winter Haven Saturday Market.

Circuit of Champion FLORIDA

Presented by Premier Tournament Group and Big Time Hoops, this Florida basketball tournament brings together teams from multiple states for exciting competition.

Summer in the Gorge

Enjoy a painting session for ages 15 and up. Instruction will be provided. You can purchase wine, beer, or non-alcoholic beverages at the bar. It is also permissible to bring your own snacks. If youd like to create your own scented soy candle before the painting, arrive 30 minutes early.

Almost There Live at Caribbean Bay - Winter Haven, FL

Almost There brings a full set to Caribbean Bay in Winter Haven, spanning rock, metal, alternative, pop, and classics with a progressive edge. The show leans into bold, unfiltered delivery rather than safe choices and may include a few originals. Frozen rum runners set the scene while the band leans into a heavy vibe.

Arabellas Pre-Show Dinner Special

Turn Tribute Tuesday into an Italian night out with an exclusive four-course pre-show dinner in Winter Haven. Begin with an antipasto choice such as creamy burrata caprese, crispy mozzarella in carrozza, or rich fiocchi al gorgonzola, followed by a fresh Insalata della Casa. For the main course, select from honey dijon glazed salmon, NY strip tagliata di manzo, fettuccine Alfredo, Arabellas homemade lasagna, or classics like piccata, parmigiana, or marsala prepared with chicken or veal. A chef-chosen dessert completes the meal. Vegetarian options are available, and most allergies can be accommodated. No substitutions are permitted; beverages, gratuity, and alcoholic drinks are not included.

Pokemon League Challenge - May 2026

This monthly Pokémon League Challenge features Standard Format play with 25 minute, best of one games. The tournament will run for 3 to 4 rounds depending on attendance and is expected to last about two and a half hours. Entry is $5. Participation is capped at 16 players, and preregistration by phone is required at 863-324-1323. Prize support includes one prize pack for each match win, an additional pack for the top four, and a pack for every participant. Players must arrive with a completed decklist that lists first and last name, Pokémon ID number, date of birth, and the exact quantities and versions of all cards in the deck. Late arrivals or missing decklists will result in ineligibility to play.

Storm Riders - Ritz Theater Winter Haven FL

Storm Riders make their first appearance at the Ritz Theatre. Ticket sales are open, and seat selection is available.

By the Moon and the Stars

Sunset Splendor

Enjoy a painting class for ages 15 and up. An instructor will guide you step by step as you create your own artwork. You can purchase wine, beer, and non-alcoholic beverages. You can also bring your own snacks. If you want to make your own scented soy candle before you paint, please arrive early. There are upgrades available.

Magic - Final Friday Pauper

Players can enter for $10. The event uses 50-minute Swiss rounds with best-of-three matches. For prize support, one ticket is awarded for each match win, plus an extra ticket for placing in the top four. Tickets can be redeemed for a variety of booster packs. First place receives a foil promo pack, and additional promo packs will be given out at random.

Vibrant Forest

Enjoy a guided painting session suitable for ages 15 and up. An instructor will provide step-by-step directions as you create your own unique artwork. You can also create your own scented soy candle before you paint, but you will need to arrive 30 minutes early if you choose to make a candle. Wine, beer, and non-alcoholic beverages are available for purchase, and you may bring your own snacks.

Live at Raise The Bar and Grill !

Attendees can enjoy live music along with food and drinks at Raise the Bar and Grill. It offers a chance to pair live tunes with something to eat and drink in one place.

Drive-In Dreams - 50' Party

Cypresswood Golf & Country Club hosts a retro celebration with DJ Dan spinning favorites, a buffet inspired by the 50s, and opportunities for door prizes. Join in contests and games, enjoy a cash bar with specialty drinks, and capture photos with classic 1950 cars. 50s attire is encouraged. Admission is $45 per person.

Smokepoint Returns to Tanners Lakeside

Smokepoint brings live music to Tanners Lakeside, creating an easygoing night out by the water. The venue offers drink selections and food, so you can relax with something to eat and sip while the band plays.

Sip Swap Swag

Bring a gently used clothing donation to Jessie’s Lounge, browse the selection, and take home items you like at no cost while enjoying drinks. This clothing swap blends sipping and sharing with a focus on giving back. All donations go to the George Jenkins Community of Hope Shelter to support families facing emergencies.

Wildflowers with a Butterfly

The Great American Beer & Wine Tasting

Main Street Winter Haven hosts a tasting experience celebrating America 250, 1776 to 2026. The annual Beer & Bubbles tradition has been refreshed as The Great American Beer & Wine Tasting, presented by Bank of Central Florida Winter Haven, to honor the nation’s 250th anniversary. Participating downtown businesses will offer pairings of American beer or wine with classic American bites. Attendees can secure tasting tickets in advance, or at the door if available, then present an ID and check in at one of two stations to collect a tasting glass and a map. Tasting tables at each stop will feature an All American theme.

Gladiator / Gladiatrix Wrestling Series

Open to wrestlers ready to compete and grow, this series offers a welcoming way to showcase skills, refine technique, and build connections within the wrestling community. Regional qualifying events are set for Des Moines, Iowa, Asheville, North Carolina, and Winter Haven, Florida, providing multiple entry points into the action. Registration is open for competitors who want to make their mark.

Save The Date - Pitties & Pearls, The Masquerade Edition

The second annual Pitties & Pearls fundraiser, presented by Adams Estate, returns as The Masquerade Edition. The event will be held at Adams Estate. Further details will be announced soon.

2026 Juneteenth Celebration

Presented by the City of Winter Haven, this annual community-wide Juneteenth celebration takes place at the new Winter Haven Recreation and Cultural Center. The event honors the significance of Juneteenth and highlights culture, heritage, and accomplishments with live music and other performances, local food and shopping from area vendors, family activities, and educational exhibits. Vendor applications and additional details will be shared soon, and the gathering centers on celebration, reflection, and unity.

Grove Roots Brewing in Winter Haven

Enjoy tavern style pizza prepared in small batches.

Fan the flames of Rock n Roll with Twizted!

Twizted returns to Out-n-About Bar and Music Lounge with another surge of rock and roll. Back to turn it up again and keep the music roaring.

Almost There Live at Somewhere Sports Bar - Winter Haven, FL

Almost There performs an outdoor parking lot set at Somewhere Sports Bar in Winter Haven, featuring rock, metal, alternative, pop, and classics. The set may include a few newly learned requests from friends, adding surprises to a high-energy night of live music.

Maurice Benard in Winter Haven, FL

An evening with Maurice Benard brings inspiration, reflection, and General Hospital memories along with a question and answer session. The star of ABC’s General Hospital, a New York Times bestselling author and host of the YouTube series State of Mind, highlights more than three decades as Sonny Corinthos. Cast in 1993, he has received multiple Daytime Emmy nominations and earned wins in 2003, 2019, and 2021. On screen he portrays a mobster who grapples with manic depression, and in his own life he has been diagnosed with bipolar disorder and advocates for mental health. Tickets are available in two options. General admission is $49, and taxes and fees apply. VIP admission is $99, and taxes and fees apply, and includes a meet and greet after the show with photo opportunities. Autographs are not included.