Events in Winter Park, FL

Pickleball at Gateway offers two back-to-back sessions and a welcoming setting for all skill levels. Beginners can learn the basics with friendly instruction, and paddles and balls are provided. The initial visit is free, then each session costs $5.

At Full Throttle Raceway & Pro Shop, the focus is on getting quicker and refining setups. Open practice gives drivers time to fine tune their cars, followed by structured test and tune runs that emphasize both speed and consistency in a relaxed, competitive setting that welcomes all experience levels. The RWYB Cash Dash crowns a single winner based on the fastest lap recorded during the event, with bragging rights and cash on the line. There are no class restrictions or performance limits, so all cars and builds are eligible. Racing uses a straightforward format with one 3 minute qualifier and one 5 minute main. Additional competition is available in AAA and Lipo classes. The goal is simple... test, tune, and chase the top of the leaderboard.

This local One Piece TCG event offers check-in through the Bandai app or in store. The entry fee is $10, and prizes are awarded as store credit.

An electric vehicle car show takes place in Downtown Winter Park, highlighting EVs and their owners. Participants planning to display a vehicle are asked to register in advance, choose the show-your-vehicle option, and include "CFEVA" in the comments for the event organizers so participants can be grouped together.

A nurturing spa day for mothers and daughters blends pampering with meaningful connection. Gentle, holistic facials for moms and age appropriate mini treatments for girls use clean skincare in a relaxing aromatherapy setting. The emphasis is on a healthy glow and soothing the nervous system, supporting wellness from the inside out. Herbal tea and light refreshments create space for unhurried conversation. Each guest makes a keepsake bracelet, and rotating beauty themed crafts invite hands on creativity, with options that may include crafting a scent roller, blending a sugar scrub, or creating a lip oil. Guided affirmations foster confidence and emotional awareness, and writing heartfelt notes to one another often becomes a favorite moment. Conversation starters, gratitude reflections, and structured connection time unfold in a peaceful, sanctuary like environment. Families appreciate the safe, clean, and welcoming setting, the gentle holistic approach to skincare, and activities that build self confidence. It suits birthdays and special celebrations and is designed to create lasting memories. This experience is ideal for moms and daughters ages 5 and up, grandmothers with granddaughters, small birthday gatherings, self love celebrations, girls spa day outings, and homeschool enrichment. Advance reservations are required and walk ins are not accepted.

Aloma Bowling Center hosts the 70th Annual Florida State 600 Club Tournament, featuring singles squads and Friendship Doubles squads offered across two days with multiple sessions each day. An annual meeting is scheduled during the event. Bowlers can compete in singles or team up for the Friendship Doubles format, with several squad options available.

TCU heads to Orlando to face UCF at Acrisure Bounce House in a conference matchup. The Knights’ high-tempo attack and charged home environment meet the Horned Frogs’ physical, defense-focused identity. With contrasting styles and a crowd known to stay loud throughout, the outcome could hinge on just a few pivotal possessions.

Teams of five take to the lanes for the 5th Annual Bowling Classic. Participants are encouraged to wear costumes or matching uniforms and will compete for trophies and prizes. Raffles and a silent auction add to the excitement. Entry is $35 and includes shoes, pizza, and a soft drink. Registration is available.

This local One Piece Trading Card Game event offers check in through the Bandai app or in store. The entry fee is $10, and prizing is awarded as store credit.

Riftbound TCG Locals offers a community-focused gathering for Riftbound players. The entry fee is $10, and prizing is available as packs or store credit.

HealingMamaStudio hosts a luxury mother and daughter tea and spa experience in Orlando that turns tea time into meaningful connection. Set in a calm, spa-inspired space, the gathering invites families to slow down and enjoy a beautifully arranged tea service with herbal blends, pastries, and light refreshments. Guests take part in creative, memory-making activities, including crafting a keepsake bracelet and exchanging handwritten affirmations, with gentle conversation prompts to support confidence and deeper bonding. An optional upgrade adds pampering touches such as mini facials, lip gloss making, and beauty crafts for a fuller spa feel. The setting is private and intimate, making it a thoughtful choice for birthdays, mother daughter dates, grandmother and granddaughter time, homeschool socials, and mommy meetups. Private bookings and customizable packages are available, and attendance is limited to keep the experience personal. Advance purchase is required, and walk-ins are not accepted.

Gather to play Warhammer games, including 40K, Necromunda, Old World, and others.

Hobby Night at Layton Gaming offers free admission. The event features raffles and a variety of sales on Dungeons & Dragons, Gunpla, Warhammer, and board game items.

This local Pokemon event features a 10 dollar entry fee, with prizes awarded as store credit.

Jason 'Gote' VanDeMaat brings live music to the Tommy Bahama Marlin Bar in Winter Park, Florida. The performance features laid back tunes with a coastal feel, creating a relaxed, fun filled atmosphere.

This YuGiOh TCG Standard event features on site check in. The entry fee is $5, and prize support is provided in the form of booster packs.

Enjoy an after-hours evening at the Art & History Museums of Maitland with complimentary gallery admission and access to the main garden. Drinks are available for purchase at the bar. Each edition features either a tour of the current exhibitions led by the Chief Curator or a free lecture from a visiting expert in art or history. Connect with a creative community while exploring art and ideas.

Explore encaustic painting in a workshop held on two days across two weeks. Participants blend beeswax, damar resin, and pigment to create their own encaustic medium and learn to use the application tools. Instruction covers essentials including layering, fusing, inlay techniques, building texture, and a range of surface treatments. By the conclusion, each attendee will have completed two paintings that demonstrate the skills learned. All materials are provided.

This community-focused group is for stroke survivors to connect with peers, talk through their journeys, and receive helpful guidance. Care partners are included and welcome. Meetings take place at Orlando Rehabilitation Hospital, offering a warm, understanding setting for conversation and support.

The Altamonte Council hosts a networking gathering that helps participants connect with area businesses and showcase their own work. Offered as a free member benefit of the Seminole County Chamber, it focuses on building relationships, sharing opportunities, and raising the visibility of your business in the community.

Celebrate community and purpose at the 2026 Legacy Gala, a benefit for Lakewood Center, which works to improve the quality of life for adults living with chronic mental illness. Hosted at the Winter Park Events Center, the evening features cocktails and hors d'oeuvres, a seated dinner, live entertainment, and one-of-a-kind auction offerings. Guests are encouraged to dress their best and be part of a meaningful night that supports Lakewood Center's mission.

Celebrate the season with a Halloween themed 5K at Blue Jacket Park in Orlando that lifts up animal shelters and animal charities. Runners and walkers are welcome, and the event is open to ages 3 and up. The race is officially timed and scored by J3 Timing, with chip timing and live results. Registration is $25 and includes a short sleeve T-shirt, a finisher medal, a chip timed race bib, live results, and finish line treats for both people and dogs. Pets are encouraged to participate, and you can take part with or without your dog. Canine companions do not need their own registration.

A family-friendly day features hands-on art workshops, face painting, a scavenger hunt, and time to draw in the garden. Complimentary admission is offered to all three museums on the National Historic Landmark campus.

A guided tour leads through the historic grounds of the Maitland Art Center, established in 1937 as a retreat for artists and recognized for its imaginative Mayan Revival architecture. Discover the lush gardens and see over 2,000 A&H carvings and murals on site.

The Page & Pen Festival returns to Oviedo Mall, welcoming readers, writers, and daydreamers. Reviving the spirit of book fair days with a modern twist, it showcases authors from the area, workshops for writers, panels on creativity, and plenty of bookish fun. Offerings range from imaginative fantasy to heartfelt memoir, so both storytellers and readers will find something that fits. Highlights include book signings with authors, giveaways, and more. Above all, it is a community celebration of imagination and creativity that embraces the idea that stories are meant to be shared.

Author Gary Zeiger will be at the Page & Pen Festival at Oviedo Mall as an attending author, welcoming visitors to stop by his table and say hello. This literary celebration brings together authors, publishers, literary agents, and other professionals who are passionate about storytelling. Guests can meet writers for conversations and book signings, listen to panel discussions and readings, take part in workshops focused on the craft of writing, and shop a market featuring books, writing supplies, and book‑inspired merchandise. The event also features live shows and hands‑on activities. Fans of fantasy, science fiction, mystery, romance, nonfiction, poetry, graphic novels, and children’s literature will find plenty to enjoy. There is no charge for entry or parking.

Step inside working studios for a behind-the-scenes look at creativity in motion. Guests can talk with resident artists, watch pieces develop, and explore the galleries with complimentary admission. This new series was created in response to community requests for more frequent, in-person connections with local artists.

Make space for focused writing at Winter Park Library. The session uses timed sprints with short breaks to keep momentum going. Participants should bring their preferred writing tools and any other supplies they like to use. Attendance is free. RSVP is also available through a free online writing community.

Trade Night at Layton Gaming offers free entry, along with free pizza, raffles, sales, and activities for kids.

The Oasis Impact Church Gala offers an evening that blends sophistication with festive spirit, all guided by clear intention. Hosted at Hilton Orlando/Altamonte Springs, this gathering centers on style, joyful moments, and a meaningful focus.

Kirtan offers a heart-centered gathering of communal singing and meditation through sound. An uplifting blend of live music, mantra, and rhythm fosters a shared sense of unity and peace. All are welcome to take part in the way that feels right, whether by singing, humming, or simply listening, and every presence adds to the collective energy. Pricing is $36 for non-members and $32 for members. Cost should not be a barrier, and scholarships are available by emailing info@magnoliawellnesscenter.org.

An all-80s dance party takes over Blue Bamboo Center For The Arts, led by Ricky Sylvia with The Buzzcatz and featuring guest vocalists Carmen Harrell-Ferreira and Naome Bradshaw. Attendees are encouraged to wear their best 80s MTV inspired outfits.

Altamonte Springs hosts a single day pop culture show at Hilton Orlando/Altamonte Springs, filling over 7,000 square feet with toys, video games, comics, die-cast collectibles, and more. A special guest will be announced. Visitors can explore vintage and modern toy lines such as Star Wars, G.I. Joe, Marvel and DC characters, Lego, Hot Wheels, Funko, Godzilla, Transformers, and Ghostbusters, along with favorites like Barbie, Strawberry Shortcake, Care Bears, and American Girl dolls. Retro gaming vendors feature selections for Atari, Nintendo, Sony PlayStation, Sega Genesis, and other systems. Comic dealers will offer both graded and ungraded books. Admission ranges from $10 to $15 depending on the ticket, and children under 12 can receive complimentary Hot Wheels or Pokemon cards.

Experience Cape Cod and New England on a tour that includes five nights at a first class hotel, dining, a whale watching outing, and an excursion to Martha's Vineyard, plus visits to the Outer Cape, Hyannis, and Provincetown. Prices start at $2,870 per person, with a $250 deposit due at registration. Booking is available by scanning the QR code on the flyer, contacting the Richland Senior Center, or reaching out to Lance Clay or Anna Peeples with Trek Travel Programs. All payments are made directly to Trek Travel by check or through the We Travel platform.

This field trip features a garden tour at FFGC Headquarters, personally guided by the FFGC President. RSVP is requested to coordinate carpooling.

The Central Florida Chapter of AAAA hosts its monthly social at Froggers Grill & Bar Oviedo, sponsored by Hatalom. Since 1994, these gatherings have offered an informal space for conversation between industry and the military community. Admission is $10 and includes beer and wings. The event serves as a chapter fundraiser, featuring a 50/50 raffle that contributes to the Scholarship Fund. Attendees can connect with friends and business associates and wrap up the workweek in a relaxed setting.

Nerd Night brings a lively evening to Oviedo Mall with free activities, special discounts, and opportunities to win prizes. Adults can stop by Wizards and Lizards to pick up a Mockbuster Membership card and get it stamped at each Nerd Night to earn prizes in December. Kids can visit Echo to color Marty and collect a stamp on a stick at each event for prizes in December, with new Marty adventure coloring pages available there every month. Disney pin traders can meet at Wizards and Lizards to trade with local collectors. Ultimate Comics offers a monthly coloring sheet featuring a new Marty alongside a member of the Mallrats band. Versus Games invites guests to paint a 3D printed starter Pokémon, with a different generation highlighted each month. This gathering happens on the second Friday of each month.

A reimagined Oviedo night market becomes The Other Side, an indoor experience devoted to the eerie, the offbeat, and the wonderfully odd. With a fresh name and vibe, it keeps its mischievous streak while turning the familiar mall into a nostalgic world where the uncanny feels right at home. Inspired by late-night mall wanderings, well-worn horror paperbacks, supernatural lore, cult favorites, urban legends, vintage gems, and misfit objects, this special edition of Mall Rat Market invites exploration. Browse a thoughtfully curated lineup of artists, makers, vintage sellers, collectors, creators, and small businesses. Discover spooky artwork, handcrafted curios, retro collectibles, alternative fashion, throwback finds, and unexpected oddities around every corner. Expect moody nostalgia, mysterious surprises, and a sense of déjà vu that is hard to shake. Whether you are searching for a new favorite artist, hunting for vintage pieces, embracing your inner mall rat, or simply looking for something different, the path points to The Other Side. Lights glow, thresholds beckon, and something strange waits within.

Phil Wickham brings the Song of the Saints Tour to Addition Financial Arena in Orlando, joined by Chandler Moore and special guest Jamie MacDonald. This stop on a 16 city U.S. run features favorites like This Is Our God, House of the Lord, and Hymn of Heaven, along with new music from the recently released Song of the Saints album, including What An Awesome God, The King Is In The Room, and Homesick for Heaven. Tickets are on sale. For the protection of attendees and buyers, third party ticket sales are not allowed on TPR event pages, and tickets obtained through third parties are not guaranteed by TPR or supported with event updates and assistance. Purchasing through the official ticketing outlet is the reliable way to secure entry.

At Blue Bamboo Center for the Arts, Callisto Sextet appears with saxophonist Jeremy Fratti for a performance that blends folk, rock, and soul through a jazz lens. The music keeps melody and storytelling in focus, shaped by a roster of leading Central Florida players. The ensemble features singer songwriter and guitarist Hannah Stokes, pianist Patrick Moreno, guitarist Abe Alam, bassist Marco Bojorquez, and drummer Jeremy Katalenic alongside Fratti. Together they bring wide-ranging experience, having worked with artists such as Ira Sullivan, Kurt Elling, Pat Metheny, and Sam Rivers, toured with the Tommy Dorsey and Glenn Miller Orchestras, and appeared at renowned rooms including the Blue Note, the Iridium, and Smoke Jazz Club in New York. The set draws on reimagined songs by James Taylor, Michael Jackson, Stevie Wonder, the Beatles, and Antonio Carlos Jobim, while also exploring modern voices like Bon Iver and Alexi Murdoch. The Howey Music Series has praised the group for a soulful, captivating sound and heartfelt arrangements that won over their audience, as noted by Emily Heumann.

Celebrate the season at Venue on Lake Lily - Maitland Civic Center with a family friendly fall gathering filled with local shopping, tasty bites, and festive fun. Browse booths from vendors and artisans for unique finds, enjoy face painting, and savor favorites from food trucks. Children are encouraged to wear costumes and pose at autumn themed photo spots to capture sweet memories. It is a welcoming way to support small businesses and spend time with friends and family. Please note that this is not a trick or treating event.

Natural Awakenings Magazine brings its pages to life at a Central Florida expo held at the Hilton Altamonte Springs near I-4. Explore local practitioners, products, and services spanning functional medicine, holistic health, mental wellness, fitness and yoga, nutrition, energy healing, and healthy living. Attendees can connect with experts, take in educational presentations, and discover new approaches to natural health in one convenient setting. Admission is free to the public. Exhibitor applications are open. Find inspiration and take the next step on your wellness journey.

Mobile Fairy Hair will be at the 5th Annual Not so Spooky Hallowfest with For the Love of Shopping. Find the Fairy Hair station indoors alongside more than 60 small businesses. Services are available on a first come basis, so plan accordingly.

Day’s Trips presents an outing to Winter Park Playhouse for Rat Pack Lounge, a musical comedy that sends Frank, Dean, and Sammy back for one night to make amends and keep a long-standing promise to the lounge’s owner. Expect signature hits like My Way, Come Fly with Me, Ain’t That a Kick in the Head, Everybody Loves Somebody Sometime, and more. The itinerary includes a bus departure from PSL with an additional pickup in Vero, travel to the theater for the performance, and time afterward to enjoy dinner in Winter Park at one of several restaurants before returning home. The price is $105 per person. Payment is due at booking. Tickets are nonrefundable but may be transferred to another person. Day’s Trips, LLC is a Florida Seller of Travel, Ref. No. ST44375.

Wrap up summer with a free, team-based scavenger hunt in Winter Park powered by the ClueRally web app. No download or account is required, simply scan a QR code to get started on your phone’s browser. Take part with a group of 6 to 12 or arrive on your own and be paired with teammates. Work together to track down locations, crack clues, and complete challenges across historic Winter Park. The group meets at the Central Park Fountain by the Amtrak and SunRail station, which is the main center fountain, not the peacock fountain in the rose garden, and the finish is back at the same spot. Top teams are announced at the end, and there are plenty of nearby options for food and drinks if you want to linger. One player per team submits answers while others use Navigator Mode to help navigate and solve along the way. This edition returns to the place where ClueRally hosted its first hunt.

Now in its third year, the Songbirds Spooktacular Halloween Parade celebrates Oviedo’s community spirit with a festive procession designed for families. What began as a modest neighborhood parade has grown into a local favorite, drawing more than 1,500 families last year with an even larger turnout anticipated. Costumes are encouraged for an evening of Halloween cheer. Participants can build a float, showcase a themed vehicle, or walk together as a group, offering plenty of ways to take part in the celebration.

An inviting evening centered on community, lively conversations, and shared celebration, paired with delicious food.

Connect with local professionals at a meetup hosted by the Altamonte Council, held on the first and third Fridays each month. Offered at no cost to Seminole County Chamber members, this gathering focuses on building relationships with area businesses and giving you a chance to highlight your company.

An opening reception introduces a new contemporary art exhibition showcasing the work of Soude Dadras. The gathering features music, a food truck, and a cash bar, and includes a moment to honor the featured artist, all set on a National Historic Landmark campus.

At Blue Bamboo Center For The Arts, Walter Parks & The Unlawful Assembly present a live concert that celebrates and reframes historic spirituals and hymns that inspire, empower, and bring people together. The group is led by guitarist and vocalist Walter Parks, a longtime sideman to Woodstock icon Richie Havens. The lineup appears as either a six piece band or a trio, with featured artists including drummer and producer Steven Williams, vocalist Ada Dyer, who is currently touring worldwide with Bruce Springsteen, and trombonist Andrae Murchison. The program weaves together roots traditions from different backgrounds, interlacing spirituals, gospel, blues, and prison work songs with swamp hollers, shaped note hymns, and Appalachian reels tied to white homesteader heritage. The performance aims to both entertain and inform by revealing the shared musical threads that run through American history.

A candlelit tribute celebrates the iconic catalogs of Queen and ABBA at Azalea Lodge in Mead Botanical Garden, bringing an intimate, multi-sensory live music experience to Orlando. A string quartet performs favorites like Dancing Queen, SOS, Money, Money, Money, Bohemian Rhapsody, I Want to Break Free, Waterloo, Super Trouper, Mamma Mia, Don't Stop Me Now, We Will Rock You, and We Are the Champions. The program lasts 60 minutes. Doors open 45 minutes before the music begins, and late entry is not permitted. Seating is assigned within each zone on a first come, first served basis. The venue meets ADA accessibility standards. Recommended for ages 8 and up, with an adult required for attendees under 16. This is a tribute performance and is not affiliated with, endorsed by, or sponsored by the original artists, their estates, or official representatives. On select dates, ensembles such as the Listeso String Quartet and the Fernwood String Quartet take the stage.

Celebrating its tenth year, BIKE 5 takes place at Mead Botanical Garden and welcomes cyclists of all experience levels. Organized by Bike/Walk Central Florida, the event brings riders together to explore nearby trails and highlight the region’s expanding network of bike friendly routes. Sponsors include Kimley-Horn, Kittelson & Associates, WAYMO, Ardurra Group, Cogent Bank, Fehr & Peers, DIX.HITE + PARTNERS, Florida Freewheelers, HDR, RSP Engineers, Traffic & Mobility Consultants, and WTS Central Florida.

An award-winning 3D mobile mammography program is coming to Oviedo Mall as part of the Florida Breast Cancer Foundation’s Race 2 Cure 5K. Presented by The Beautiful Gate, the nationally recognized Mammograms After Sunday Service program focuses on health equity and has earned back-to-back national awards. It brings convenient 3D mammography screenings to the community and is designed to make prioritizing breast health simple and accessible for those with insurance and those without. Uninsured Florida residents may qualify if they live in the state, do not have health insurance, have not had a mammogram within the past year, and meet age or risk criteria. Eligibility includes being 40 to 64 years old, or being under 40 with a first degree family history of breast cancer or with symptoms. Income should be at or below 200 percent of the poverty level, and women of any age who have completed treatment for breast cancer may also be eligible. Insured Florida residents who have not had a screening mammogram within the past year can schedule as well. Those at average risk should begin screening at age 40, and most health insurance plans cover screening mammograms with no out-of-pocket cost. Florida women who are insured can schedule directly with 3D MammoLink. Appointments are limited, and participants who schedule and keep their appointment and complete a virtual breast health session receive a free gift card.

Discover how a small sketch transforms into a public mural in this hands-on workshop devoted to real-world techniques. Over four days, participants will paint a permanent wall at the Art and History Museums Maitland Campus using a design selected in advance. Guidance includes preparing the site, getting the surface ready, setting up a projector, mapping with a grid, creating accurate outlines, and applying paint at large scale. The experience is well suited for studio artists seeking practical mural skills and serves as an introduction to large-scale public art. Basic experience with traditional drawing and painting is recommended. Scheduling is weather dependent. Upon completion, participants receive on-site credit and a project they can proudly add to a professional portfolio.

Orlando’s largest celebration for people with locs unfolds amid the scenic setting of Cranes Roost Park, highlighting the journey, expression, and culture of locs. Expect high-energy sets from live DJs alongside performances by local talent, plus creative showcases featuring artists, designers, models, locticians, and fashion centered on locs. A curated marketplace brings vendors selected with the loc community in mind, offering plenty to explore and discover. Whether locs have been part of someone’s life for years or they are just beginning, attendees can connect, shop, and celebrate in a space that honors the history and beauty of this style.

Boys Town Central Florida marks 40 years of service to children and families, celebrating a legacy that has touched more than 47,000 lives. The Building Brighter Futures Gala honors this milestone with an uplifting evening of storytelling, reflection, and recognition of the community support that opens doors for underserved youth. Hosted at The Wedding Barn in Oviedo, the event highlights needs across Central Florida and the path ahead for youth aging out of care and those experiencing homelessness through new program expansions. Proceeds from tickets, tables, and sponsorships directly support vital care programs for foster and at-risk youth and their families. Tickets are $150 per person or $1500 for a private table of ten. Registration is required to confirm attendance.

A touch of Monte Carlo comes to Maitland as The Venue on Lake Lily presents an elegant Gala Monte Carlo that blends entertainment, connection, and purpose. The evening features a headline performance by nationally recognized vocalist Michael Andrew, acclaimed for bringing the American Songbook to life in the tradition of Frank Sinatra, Dean Martin, and Bobby Darin. Guests can enjoy casino-style experiences, gourmet tastings from select caterers and restaurants, wine and spirit pairings, and both silent and live auctions, along with time to gather with friends on the lakeside veranda. At its heart, the gala raises support and awareness for three nonprofit causes. The National Pediatric Cancer Foundation advances research to help end childhood cancer, United Abolitionists works to stop human trafficking and support survivors, and IDignity helps people secure essential identification documents that restore access, stability, and dignity. The Venue on Lake Lily welcomes participation from local businesses, families, and community partners as sponsors, auction item contributors, attendees, or Champions for the Cause. Every ticket, bid, and sponsorship helps transform a memorable evening into meaningful support for children, families, and individuals in need.

Recently featured on the History Channel series Pawn Stars and honored as the Society of American Magicians' Magician of the Year, Niels presents a singular blend of comedy and magic at Blue Bamboo. The show offers an evening of laughter, astonishing feats, and unexpected moments created with adults in mind.

Hosted by the Longwood Council, this monthly Lunch & Learn takes place on the third Monday and serves as a Seminole County Chamber benefit designed to help participants network and connect with area businesses. Lunch is provided.

Songs, stories, and art fill a gentle, garden-based program created for babies and toddlers and the special adult in their lives. Held in the main garden on the historic grounds of the Art & History Museums, it includes a themed circle time, read-aloud moments, and a simple art activity designed for the youngest creatives. A snack is provided. The recommended age is under 3 with a parent, grandparent, or caregiver, and older siblings are welcome. Space is limited and pre-registration is required, with registration closing two days before the program date; email Jcohen@artandhistory.org to reserve a spot. Plan to arrive about five minutes early to allow time to park and walk to the garden, and feel free to bring a picnic blanket for your family. This free program is presented by the Art & History Museums of Maitland and supported as part of A&H’s 2025-26 Free Family Programs through a grant from the Duke Energy Foundation.

Take part in a guided walk across the historic grounds of the Maitland Art Center, established in 1937 as an artists' retreat and celebrated for its imaginative Mayan Revival design. Explore lush gardens and encounter more than two thousand carvings and murals connected to A&H.

Spend a day on the course with the OWS Chamber at Twin Rivers Golf Club, featuring a scramble format with teams of four that welcomes seasoned golfers and newcomers alike. Start with breakfast, play a full round, then cap it off with a celebratory reception with awards and lunch, all in a relaxed, energetic environment that makes it easy to connect with local businesses and community leaders. Pricing is $175 for individuals, $300 for pairs, and $500 for teams of four.

Cigano Swing brings its gypsy jazz artistry to Blue Bamboo Center for the Arts, drawing on the tradition of Django Reinhardt and the Hot Club de France while adding fresh energy. The quartet features André Santana on lead guitar, Kyle Jones on bass, Allen Kooken on rhythm guitar, and Emily Cole on vocals. Their sound blends nimble improvisation, driving swing rhythms, and graceful, nostalgic singing for music that feels both classic and new. The group has sold out shows at this venue, appeared at College Park Jazz Fest, headlined the New Smyrna Beach Jazz Festival, and performed live on 89.9 WUCF Jazz. Appearances for Seminole State College and First Institute reflect their place as one of Florida’s leading gypsy jazz ensembles.

The 13th annual HOWL-O-WEEN celebration brings a dog walk and a playful costume contest for canines to Cranes Roost Park. Organized by Franklin’s Friends, the event features opportunities to meet adoptable pets, explore pet friendly vendor booths, and enjoy food trucks, music, and more. Registration is $20 in advance or $25 at the door. Prizes will recognize the top three individual fundraisers and standout canine costumes. Sponsorship and vendor booth options are available. Last year more than 500 supporters helped raise over $48,000 for local animal welfare, and every contribution benefits Franklin’s Friends as it provides lifesaving support to pets and the organizations that care for them.

Guided by Dennis and Kathy Lang, this session offers a four-element movement journey. Begin with air through mindful pranayama to center the breath. Flow into water with supple, continuous motion. Stoke the fire with expressive, freeform dance and intentional rhythm. Settle into earth with quiet presence as Dennis provides live music. The experience invites release, reconnection, and restoration through breath, movement, and rhythm. No prior dance experience is required. Bring a yoga mat if you prefer, and mats are available to borrow.

Oviedo Mall's Annual Monster Dash 5K is a 5K with a Halloween theme welcoming runners, walkers, and families. Costumes are encouraged, from monsters and superheroes to ghosts, witches, vampires, pumpkins, or something completely original. The event offers fun for all ages, a lively race atmosphere, event goodies, and plenty of chances for memorable photos. Whether chasing a personal best, enjoying a stroll with friends, showing off a standout costume, or running for medals, participants can look forward to fitness, fun, and festive fall memories from this seasonal tradition. Registration is open.

Austin Formula 1 fans can gather at the Hourglass Brewing Longwood Taproom for a watch party centered on the Austin F1 race. Presented with Orlando F1 Fans, the viewing pairs high-speed action on screen with cold beers in a relaxed taproom setting. Admission is free, sponsor support adds to the buzz, and fans are encouraged to bring their F1 spirit.

Although the setting leans Halloween, the plan is to get a head start on Christmas with a Secret Santa inspired ornament swap. Bring one wrapped ornament valued between five and ten dollars. Participants will draw numbers to set the order, then take turns choosing a wrapped ornament or taking one that has already been opened. There is a limit of two steals, and no steal backs during the same turn.

Take advantage of free admission to the galleries, purchase a drink from the cash bar, and wander the main garden after hours on the last Wednesday of each month. Each month features complimentary tours of the current exhibitions led by the Chief Curator or a free lecture by a visiting expert in art or history. Connect with a creative community at the Art & History Museums of Maitland.

This A&H curator-guided gallery tour offers an in-depth look at the exhibition Vilomah: Against the Natural Order, tracing its path from initial concept and creation to the curatorial choices that shape its presentation. The evening begins with a 45 minute tour led by Chief Curator Dan L. Hess, followed by conversation with complimentary food for the remainder of the event. Attendees may arrive with a friend or a date, or attend solo and connect with others who share an interest in the arts.

At the Winter Park Community Center, the 50+Plus FYI Expo brings together local organizations and knowledgeable professionals with resources for adults 50+, caregivers, and families. Explore information on insurance, housing, transportation, Social Security, Medicare, VA, disability, and health care while connecting with experts who can point you to programs and services that fit your needs. Enjoy free admission and free parking, enter for door prizes, and get a keepsake with caricatures by Irina. Hosted by the City of Winter Park.

A community Halloween display in the Orlando area supports an animal rescue charity and showcases many handmade props. The organizers expect to seek fresh ideas and hands-on help with additional DIY elements this year, and they plan to share requests for assistance in upcoming posts.

Oviedo Mall hosts its annual Kid Crew Mall-O-Ween Trick-or-Treat, a free, family-friendly celebration for children 12 and under. Costumed kids can stroll through the mall and visit participating shops to pick up candy and treats, available while supplies last. The festivities happen entirely indoors, offering a comfortable and safe option in place of neighborhood trick-or-treating. Families can enjoy exploring the mall together, showing off creative costumes, and making Halloween memories at a popular tradition in Oviedo and Central Florida.

Experience the Mexico City Formula 1 race with a watch party at Hourglass Brewing Longwood Taproom. Presented in collaboration with Orlando F1 Fans, this gathering highlights desert circuit excitement and fast-paced action alongside cold brews. Entry is free, so bring your F1 enthusiasm. Sponsors are acknowledged for helping power the event.

At Blue Bamboo Center For The Arts, the Allan Vache Swingtet presents a program of swing that highlights music connected to Benny Goodman, Duke Ellington, Count Basie, and more. The lineup includes Allan Vache on clarinet, David Jones on trumpet and cornet, Mark McKee on piano, Jake Jones on guitar, Charlie Silva on bass, and Ed Metz on drums.

The Altamonte Council hosts small business networking on the first and third Friday of each month. Offered as a free member benefit of the Seminole County Chamber, this gathering focuses on networking, connecting with area businesses and spotlighting participants' businesses.

Broadway and Hollywood share the spotlight in a high-energy concert that flows from stage classics to silver screen favorites in one continuous experience. Signature numbers span eras, from Lullaby of Broadway and Hooray for Hollywood to powerhouse selections like The Impossible Dream and All I Ask of You. The set also weaves in beloved hits including Fever, That’s Amore, Over the Rainbow, Copacabana, 9 to 5, and Sweet Caroline, along with pulse-raising medleys celebrating Gershwin and Cher. Expect playful duets, sweeping ballads, and clever surprises that keep the music moving. Led by the award-winning pair Cordone & Kilgore, this production delivers a full evening of big tunes and memorable moments from start to finish.

Introduce babies and toddlers to the pool with a free, guided clinic focused on water safety for families new to British Swim School. Held at LA Fitness Altamonte Springs, this session brings parents or guardians into the water with their children to learn and practice essential skills together. Instruction covers floating, safe ways to enter and exit the pool, and techniques for staying calm in the water. Participation is limited to new students, and every attendee will be in the pool with a caregiver. There is no fee, and registration is required. Please bring towels, water bottles, and a change of clothes.

Take a guided tour of the historic Maitland Art Center, established in 1937 as an artists' retreat and known for its distinctive Mayan Revival style. Walk through the gardens and see more than 2,000 carvings and murals across the A&H grounds.

Oviedo Mall’s Community Wellness Fair offers a full day centered on every part of well-being, including physical health, mental balance, family life, finances, and everyday routines. Area professionals, businesses, and community organizations will be available with guidance and services to help you take practical steps toward feeling your best. Explore vendor booths, learn about new options, ask questions, and build supportive connections. Admission is free and open to all, and you are welcome to come with family or friends and spend time focusing on yourself.

Visitors can explore working studios, meet the artists, watch new pieces take shape, and enjoy complimentary entry to the museum. The program was launched in response to community feedback requesting more consistent chances to connect with artists from the area.

Assel Jean-Pierre, a pianist, composer, and recording musician of Haitian-American heritage, appears at Blue Bamboo Center For The Arts with music shaped by conservatory technique, jazz improvisation, and the vibrant pulse of Caribbean and Latin styles. Born in New York and now based in Orlando, he has cultivated a personal sound driven by emotion, rhythmic spark, and a storyteller’s touch at the piano. He earned degrees in classical piano and in jazz and composition at the University of Central Florida, and his releases include Hymns of Meditation for the Soul, Hymns for Tots, and A Christmas Story by the Jean-Pierre Pianists. Highlights from his career include appearances at Carnegie Hall with Joey Alexander and Valentina Lisitsa, the NFL Pro Bowl Halftime Show with Jordan Fisher, Judson’s Live in Orlando, SOB’s in New York, and the Ocean Drive Promenade Music Series in Miami Beach. Known for leading the Assel Jean-Pierre Trio, he delivers dynamic sets that interlace jazz, classical, and global influences into an immersive live experience.

This event has moved to Lake Lily Park. Please note the location change.

Enjoy a Brazil Formula 1 watch party at Hourglass Brewing’s Longwood taproom in collaboration with Orlando F1 Fans. Expect high speed action, desert circuit thrills, and ice cold brews. Entry is free, and fans are encouraged to bring their love for F1. Thanks to the sponsors for fueling the excitement.

Experience an intimate candlelit concert celebrating the music of Taylor Swift. Talented musicians perform heartfelt renditions of her greatest hits while the setting glows with soft candlelight, creating an enchanting atmosphere. Whether you know every lyric or simply enjoy live music, this tribute offers a warm, memorable evening.

The Central Florida Chapter hosts a recurring social that has brought people together since 1994. Each month, the gathering offers a relaxed setting for conversation between industry professionals and the military community. Admission is $10 and includes beer and wings. The event raises funds for the chapter and includes a 50/50 raffle that supports the Scholarship Fund. It is a casual way to wrap up the workweek while networking with friends and colleagues in support of Army Aviation.

Nerd Night at Oviedo Mall brings together participating shops for an evening of free activities, special discounts, and prize opportunities. Adults can pick up a Mockbuster Membership card at Wizards and Lizards and collect a stamp at each event toward December prizes. Kids can visit Echo to color Marty and get Marty’s stick stamped at each Nerd Night for a chance at December prizes, with new Marty adventure coloring pages available every month. Disney pin traders can meet fellow local collectors at Wizards and Lizards. Ultimate Comics features a monthly coloring sheet highlighting Marty and a member of the Mallrats band. Versus Games invites participants to paint favorite 3D printed starter Pokémon, with a different generation featured each month. This event recurs on the second Friday of every month.

Bad luck gets a playful twist at a Friday the 13th themed night market that turns the mall into a showcase for vintage finds, offbeat art, handmade creations, and curious keepsakes. Expect nods to superstition like black cats and shattered mirrors, charms and ominous signs, retro throwbacks, eerie ambiance, and unexpected discoveries. Attendees can browse a wide mix of local sellers, uncover one of a kind pieces and collectibles, and enjoy bites and sweets from mall dining spots while exploring alongside collectors, creatives, and the simply curious. Presented as part of a monthly indoor market series at Oviedo Mall that spotlights nostalgia, creativity, community, and a love for the wonderfully odd. Entry is free. No misfortune required.

The National Ovarian Cancer Coalition presents its annual Together in TEAL Walk, a community event dedicated to a future where no one loses their life to ovarian cancer. The walk unites the TEAL community to advance prevention and cure efforts while supporting survivors and their caregivers. Eleven gatherings are taking place across the country this year, and a virtual option allows those without a nearby event to participate with family and friends in their own communities. Participants come together to honor survivors, remember loved ones, and raise critical awareness, turning advocacy into meaningful action in the fight against ovarian cancer. For details on participation, sponsorship, or volunteer opportunities, contact NOCC Regional Manager Nikki Coppola at ncoppola@ovarian.org.

The Man of Many Faces returns to Florida to entertain local audiences. This welcome-back appearance gives fans an opportunity to see him perform again.

Making its first appearance at Blue Bamboo, The Ultimate Santana Tribute Band brings a high-energy salute to the music of Carlos Santana. The set traces the journey from early Woodstock-era grooves to the chart-topping sounds of Supernatural and more, delivered with polished musicianship and faithful arrangements. The unmistakable Latin rock pulse is front and center, all in an intimate setting for a close-up concert experience.

Presented by Writer’s Atelier, this write-in at Winter Park Library features timed writing rounds with brief pauses between them. Participants should bring their preferred tools and any additional materials they need to work. Admission is free.

The Longwood Council hosts a recurring Lunch and Learn held on the third Monday each month. As a Seminole County Chamber benefit, it offers a friendly setting to meet and build connections with area businesses. Lunch is provided.

Little ones and their favorite grown-up can enjoy songs, storytelling, and simple art-making in the main garden on the historic grounds of the Art & History Museums of Maitland. The session features a themed circle time, storytime, and an age-appropriate art activity, with a snack provided. It is designed for children under three with a parent, grandparent, or caregiver, and older siblings are welcome. Space is limited and advance registration is required. Please allow time to park and walk to the garden, and consider bringing a picnic blanket for your family. This free program is presented by the Art & History Museums of Maitland and is supported in part by a grant from the Duke Energy Foundation as part of A&H’s Free Family Programs.

Taylor Swift’s music is reimagined for strings in a candlelit setting at The Azalea Lodge at Mead Gardens in Orlando. This 60 minute concert offers an intimate, multi sensory atmosphere, with seating assigned within each zone on a first come, first served basis. Doors open 45 minutes before the performance begins, and late entry is not permitted once the concert starts. The tentative set features songs such as Love Story, Anti-Hero, Cruel Summer, Shake It Off, and You Belong With Me, alongside medleys from Red, Reputation, Folklore, and 1989, plus The Fate of Ophelia. Performances feature the Fernwood String Quartet on select dates, with another date by the Listeso String Quartet. Attendees must be at least 8 years old, and anyone under 16 must be accompanied by an adult. The venue is ADA compliant. This is a tribute experience and is not affiliated with, endorsed by, or sponsored by the artist or their representatives.

Mead Botanical Garden hosts an evening of classical music by candlelight featuring Vivaldi’s Four Seasons performed live. Each movement paints spring, summer, autumn, and winter in sound while skilled musicians play within a warm, flickering glow. The ambiance and music come together for a serene and memorable experience.

Altamonte Council offers a recurring small business networking meetup that helps participants connect with local professionals and showcase their companies. This gathering is a free member benefit of the Seminole County Chamber, providing a friendly setting to build relationships and share what your business provides.

At Blue Bamboo Center For The Arts, local favorite Michael Andrew teams up with internationally acclaimed British saxophonist, vocalist, and bandleader Ray Gelato, known as “The Godfather of Swing,” for an evening that channels the golden age of Las Vegas and the spirit of the Rat Pack. A fixture on the international jazz and swing scene, Gelato has performed for HM Queen Elizabeth II and at leading festivals and concert halls across Europe and the United States, bringing high-energy playing and a charismatic stage presence. Backed by a six-piece band featuring piano, upright bass, drums, trumpet, trombone, and saxophone, the duo offers a stylish mix of sophistication, humor, and timeless songs associated with Frank Sinatra, Dean Martin, Bobby Darin, Louis Prima, and Sam Butera. Expect beloved favorites such as “Come Fly With Me,” “Fly Me to the Moon,” “New York, New York,” “My Way,” “Ain’t That a Kick in the Head,” “Mack the Knife,” “Buona Sera,” and “That Old Black Magic,” along with toe-tapping rhythms, smooth vocals, and vintage Vegas flair.

An outdoor holiday pop up market at Adjectives Market brings together food trucks and as many as 40 new vendors. Explore handmade goods, original artwork, and distinctive treasures suited for gift giving or a personal treat. The event highlights local creativity and a lively community vibe, with artisans and small businesses sharing their latest creations.

Capture the spirit of the season during a cozy in-studio mini session in Longwood, FL, styled with milk, cookies, soft blankets, and twinkling lights. Tailored for little ones, these 15-minute sessions focus on relaxed, genuine smiles and nostalgic holiday charm. Each booking includes 10 digital images for $275, secured with a $75 nonrefundable retainer. Festive pajamas or comfy winter outfits are encouraged to complete the look. Perfect for holiday cards and gifts for grandparents, with limited availability and the possibility of additional appointment slots being added.

At Blue Bamboo Art Center, the Groove Sleighers deliver a festive set that flips classic Christmas music into a vibrant mix of soul, funk, swinging jazz, and rock and roll. This Orlando group reimagines favorites such as Have Yourself a Merry Little Christmas, Jingle Bell Rock, Santa Claus Is Coming to Town, and All I Want for Christmas Is You with polished harmonies, punchy horns, and rhythms built for the dance floor. The performance blends nostalgia with new sparkle, encouraging swaying, singalongs, and plenty of holiday cheer.

Hip hop favorites take on a new glow as the Listeso String Quartet performs orchestral renditions by candlelight at The Azalea Lodge at Mead Gardens in Orlando. Across a 60 minute program, expect string takes on Gangsta’s Paradise, I Like It, Passionfruit, and Swimming Pools, along with medleys honoring Jay-Z, Outkast, Lauryn Hill and the Fugees, 2Pac, The Notorious B.I.G., Dr. Dre, and Eminem. Doors open 45 minutes before the performance and there is no entry after the music begins. The venue is ADA compliant. Seating is assigned on a first come first served basis within each zone. Guests must be at least 8 years old, and anyone under 16 must attend with an adult.

Experience the Qatar Grand Prix with fellow F1 fans at Hourglass Brewing’s Longwood taproom. Enjoy the high-speed action from the desert circuit along with cold brews from the bar. Orlando F1 Fans is collaborating on the gathering, and sponsor support adds to the excitement. Admission is free, so bring your racing passion and settle in for every turn.

The Palm Beach Society Orchestra brings its elegant sound to Blue Bamboo Center For The Arts, carrying forward the legacy first forged as the Grand Floridian Society Orchestra. For decades, that much-loved six-piece group filled Disney’s Grand Floridian Resort & Spa with swing, jazz, Disney favorites, and timeless standards, creating a charming and nostalgic atmosphere for guests. This concert continues that tradition with a vibrant program that spans eras and styles, from American Songbook gems to Disney melodies and big band jazz classics. The ensemble’s evolution from its Grand Floridian origins to today’s Palm Beach Society Orchestra reflects the musicians’ resilience and dedication, ensuring that sophisticated live music remains at the heart of every performance.

Day’s Trips presents a group outing to Winter Park Playhouse for A Christmas Survival Guide, a comedic musical that lightens holiday stress with laughter and song. Following a cheeky handbook, the characters navigate the season in search of what truly matters, blending familiar holiday tunes, inventive medleys, and new comic numbers for a mix of humor and warmth. The trip travels by bus, departing from PSL with an additional pickup in Vero, then continues to the theater for the performance. After the show, the group spends time in Winter Park for dinner at individual expense, with several restaurants available, and then returns home. The cost is $105 per person, payment is due when booking, and tickets are nonrefundable but transferable. For questions or to reserve a seat, call or text 908-230-6553 or email DayTripDayna@gmail.com. Day’s Trips, LLC is a Florida Seller of Travel, Ref. No. ST44375.

The CFCArts Community Choir presents Believe: A Christmas Celebration, bringing together more than 300 singers with members of the Symphony Orchestra for a concert that journeys to the heart of the holiday season. This immersive program focuses on the enduring power of belief and pairs favorite Christmas music with touching narratives that reflect joy, hope, and resilience. Expect selections from A Muppet Christmas Carol and How the Grinch Stole Christmas, time honored classics like "Noel" and "God Rest Ye Merry, Gentlemen," and songs ranging from the playful "I Want a Hippopotamus for Christmas" to the reflective "My Grown Up Christmas List." The program also features Josh Groban’s rendition of "Believe" from The Polar Express. The performance includes theatrical effects such as fog, haze, and bright or flashing lights, which may affect those with light sensitivities. Ticket pricing: Standard $15, Prime $23, Premium $30. Lap held children age 3 and under are free. Groups of eight or more save 20 percent off regular pricing with code Holiday26 when booking online. For questions about group sales, including payment by check or over time, the box office can be reached at 407-937-1800 x1.

Hosted by the Altamonte Council, this small business networking gathering is a complimentary benefit for Seminole County Chamber members. It provides opportunities to connect with area businesses, exchange insights, and showcase your company. The emphasis is on building relationships and increasing visibility within the local business community.

Experience a guided walk through the historic grounds of the Maitland Art Center, established in 1937 as an artists retreat and noted for its distinctive Mayan Revival design. The route winds through verdant garden spaces and highlights a collection of over two thousand A&H carvings and murals, offering a close look at the site’s architecture, artwork, and landscape.

Vivacity sets the stage for a spirited holiday concert filled with sing along moments and swinging takes on favorite seasonal songs for listeners of every age. The program features xylophonist Heather Thorn with the Vivacity band, joined by special guest Adrian Cunningham, the Australian born and New York based saxophonist, clarinetist, flutist, vocalist, and award winning multi instrumentalist. Cunningham has recorded with Jeff Hamilton, John Clayton, and Ted Rosenthal on his album Jazz Speak on Arbors, which reached the top 20 on the US JazzWeek charts. He performs with Wycliffe Gordon and his International All Stars, and from 2014 to 2017 he led the saxophone section with the Grammy award winning Vince Giordano and the Nighthawks, a 1920s swing orchestra in New York City. He has been described as indispensable to New York jazz. Heather Thorn brings internationally recognized xylophone artistry, with appearances at the New Orleans Jazz Museum and as the headliner for Festival I Love Jazz in Brazil in 2019 and again in 2022. She appeared as a featured guest soloist with her band for the Orlando Philharmonic Holiday Pops in 2021, showcasing arrangements by Michael Andrew and Dave Mackenzie. In 2026 she served as a guest artist at the Paris Conservatory in France and at universities across the United States, and her local credits include performances at Blue Bamboo Center for the Arts, Timucua, the Sea World Christmas Celebration, Suncoast Jazz Festival, New Smyrna Beach Jazz Festival, and with the Walt Disney Orchestra. Local jazz favorites round out the ensemble, including Krissy Vavrek and Amy Parnell on vocals, Greg Zabel on upright bass, Paul Parker on drums, Bob Thornton on piano, John Depaola on trumpet, and Harold Johnson, leader of the Palm Beach Society Orchestra, on trombone, along with other surprise guests.

Taylor Swift’s hits are reimagined for strings in a candlelit tribute at The Azalea Lodge at Mead Gardens. Candlelight concerts pair live performance with an intimate, multi-sensory ambiance, turning this Orlando venue into a warm, glowing setting for favorite songs and themed medleys. Expect selections such as Love Story, Anti-Hero, Cruel Summer, You Belong With Me, and Shake It Off, along with medleys inspired by Red, Reputation, Folklore, and 1989, plus The Fate of Ophelia. The experience runs about 60 minutes, doors open 45 minutes beforehand, and late entry is not permitted. Guests ages 8 and older are welcome, with anyone under 16 accompanied by an adult. The venue is ADA compliant, and seating within each zone is assigned upon arrival on a first come, first served basis. Depending on the performance, the program is presented by the Fernwood String Quartet or the Listeso String Quartet. This is an independent tribute and is not affiliated with, endorsed by, or sponsored by the artist or their representatives.

An annual holiday celebration at the Center for Health & Wellbeing brings festive activities for consumers registered with CIL, the disability community, and their friends and loved ones. Look forward to craft activities, seasonal treats, and a cheerful visit from Santa. Consumers registered with CIL are invited as guests, while all other attendees will need to purchase tickets.