Events in Four Corners, FL

The Osceola County Senior Expo brings together dozens of local organizations that support older adults and their families in Osceola County and nearby communities. Attendees can meet with specialists to explore Medicare coverage, assisted living, mobility solutions, independent living, veterans benefits, audiology, senior travel, health insurance, home care, medical equipment, hospice care, financial planning, legal assistance, aging in place home improvements, eye care, physical therapy, and more. It is a chance to ask questions, compare options, and discover resources tailored to senior needs.

Take a few minutes for your health and let it make a lasting difference. Osceola County is partnering with UCF Health to bring free medical and health screenings to the Robert Guevara Community Center through the Mobile Health Clinic. Available services include blood pressure checks, cholesterol and diabetes screenings, and hearing evaluations. Care is provided by UCF faculty healthcare professionals together with students, helping residents stay informed, proactive, and connected to ongoing care.

UNO Pizzeria & Grill in Kissimmee features a festive pumpkin decorating activity where guests can get creative together. Participation in the craft is complimentary with a food purchase, and the event welcomes all ages, from first timers to experienced decorators. Kids meals start at $6.99. Availability is limited, so reservations are recommended to secure a pumpkin.

A safe and festive Halloween trunk-or-treat brings together local organizations from Haines City and Davenport. Participants will decorate their vehicle trunks and share candy and small treats with attendees.

This biweekly meeting from the CLG Hunters Creek Chapter takes place at Sajoma Latin Fusion in Kissimmee and centers on building relationships that turn into real business and referrals. The atmosphere is energetic and results driven, with a focus on meaningful conversations that lead to practical outcomes. It welcomes business owners, entrepreneurs, real estate professionals and lenders, contractors and other service providers, marketers, creatives, and professionals aiming to grow locally.

Spend an evening playing bingo at Chick-fil-A Four Corners with food and plenty of fun. Costumes are optional, so bring friends and enjoy a lighthearted outing.

Every Tuesday evening, the FloDash Events and Dash Sports run and walk group meets at The View Clermont. Participants can choose a 45 minute walk or run, track their miles, and earn milestone prizes. The outing finishes back at The View for time to socialize. Open to all, including families, individuals, and dogs.

Puzzles Entertainment brings a weekly Jukebox Bingo to The Friar Tuck, combining the spirit of Name That Tune with classic bingo. The experience includes music, singing, dancing, and opportunities to win. It is free to play, with four rounds that produce four winners, and prizes include free drinks and gift certificates.

Puzzles Entertainment hosts a weekly Jukebox Bingo game at The Friar Tuck that blends music recognition with classic bingo. The event features four rounds with four winners, and prizes include free drinks and gift certificates. Expect an upbeat atmosphere with music, singing, and dancing as players mark their cards and compete to win.

Led by Ride Advocate Keith, the Wednesday Social group ride welcomes entry-level cyclists for a no-drop outing of roughly two and a half hours at an easy to moderate pace of about 15 miles per hour on the West Orange and South Lake Trail. Expect an average distance of around 32 miles, a friendly atmosphere, and support for practicing group riding fundamentals. Helmets are required. This is not a sanctioned race or event and participation is at your own risk. Route information is provided as planning guidance only and may be incomplete or inaccurate, so each rider is responsible for personal research and safety decisions. Cycling carries inherent risks, and participants assume all responsibility for any outcomes, including injury or property loss. Check weather, surface conditions, and possible closures, follow all applicable laws and land use rules, and bring appropriate safety and navigation gear.

In honor of National First Responders Day, first responders are offered a complimentary meal in appreciation of their courage, dedication, and service. Choose from Strawberry Fields Salad, Blackened Chicken Pasta, a Pulled Pork Sandwich, Margherita Pizza, or the Backstage Burger. Take a well deserved break and enjoy a meal at no cost. A valid first responder ID is required to redeem.

This kid-focused community gathering prioritizes safety while creating a warm, welcoming atmosphere for children. The environment is designed to be secure and family friendly so kids can enjoy themselves and caregivers can feel comfortable. Expect a positive experience centered on providing a protected space for young attendees.

Build the knowledge and skills needed for responsible concealed carry at a focused Florida CCW class in Clermont, held at Marco Hunt Club. The course fee is $50. This single session satisfies the training requirement for the Florida Concealed Carry Permit and includes a range component with a guided shooting exercise. Weapons and ammunition are not offered for sale by the organizers.

Old Town's Bike Night returns to the Old Town Entertainment District in Kissimmee as a free, biker-friendly meetup welcoming all makes and models of touring motorcycles, including Harleys, Indians, trikes, and slingshots. This gathering highlights the camaraderie of the riding community, with the familiar rumble of engines bringing riders together throughout Old Town. Participants must have a valid driver's license and proof of insurance. Colored patches are not permitted.

At The Friar Tuck, host Ken Franzetta spotlights original music in an easygoing showcase for local songwriters. Artists can bring an acoustic guitar, add their name to the sign-up, and share their own songs on stage. A house keyboard is on hand for those who prefer keys. Covers are not part of the program, the focus is entirely on original material. Listeners can relax with dinner and a couple of cold pints while discovering new voices from the community.

FloDash Events and Dash Sports host a run and walk group at Dash Sports in downtown Clermont. Participants choose a 45 minute run or walk, track their miles, and earn prizes for milestones while connecting with others. The outing wraps up at Sud's Saloon for more socializing. All are welcome, including families, singles, and dogs.

A friendly group of women gathers at the Kissimmee Woman’s Club to play the Hand, Foot and Toe card game in a relaxed, welcoming setting. The social side is as important as the game, with plenty of conversation, laughter and connection. Both seasoned players and those new to the game take part, with guidance available for anyone learning or brushing up on the rules. Attendees can bring lunch and may come solo or with a friend.

Old Town’s Karaoke Nights put the mic in your hands on the Main Stage next to Southern Breeze. From powerhouse singers to enthusiastic first timers, all voices are welcome. Sing solo or with friends in a relaxed, upbeat setting that celebrates every performance. It is a chance to share favorite songs, have fun, and enjoy a turn in the spotlight.

Enjoy live music at @twobridgespub as @daveygilmore performs a set of Britpop and UK classics.

A themed trivia night devoted to The Nightmare Before Christmas takes place at Pizza Hut, featuring questions that span Halloween Town, Christmas Town, and the areas that connect them. Teams compete for first place and can enjoy pizza during the game.

ARTS Unlimited, LLC presents Night of the Living Dead Live, an officially authorized stage tribute to the 1968 film with a comedic edge. Six strangers take shelter in a farmhouse while a mass of brain-hungry zombies surrounds them. The production dives into the spirit of the original, the style of the 60s, and the film’s broad influence on horror. With multiple possible endings, the characters face a string of predicaments and antics as they try to make it through the night. A costume contest will be held during select performances. To participate, a ticket is required and costumes must be family friendly. Masks and heavy makeup that prevent clear facial recognition are not permitted. Weapons, blood, and gore are not allowed. Two winners will be selected at each participating performance. Entry may be refused to anyone who does not follow the costume rules, and no refund will be issued if you are asked to leave.

Set out on a spirited group ride that spans roughly 42 miles, keeping an average speed between 18 and 20 mph. The route blends roadway sections with a bike trail, heading to Apopka and returning to the starting point. Helmets are required, and lights are recommended for safety. Please observe all traffic laws and take part at your own risk. Keith leads this ride.

A Halloween-themed high tea serves scones alongside a mix of sweet and savory treats, paired with a trio of teas. The experience spans three courses in a lively, festive setting. Attendees can sing along to favorite Halloween songs for an extra touch of fun.

Friday nights rev up with a showcase of show-quality 1964 and newer muscle cars alongside hot rods and classics from 1985 and earlier. The show and cruise are free for car owners and free for the public. Registered vehicles are welcome to participate in the cruise. Classic car participants should enter Old Town from Highway 192 beneath the east side of the Jukebox signs to meet event staff, then follow a security escort along the brick streets. Please avoid driving on the bricks unless given permission. Old Town Cruisers earn an entry each time they cruise on Fridays and Saturdays during the month, with a $1,000 winner drawn after the final Friday cruise and another $1,000 winner after the final Saturday cruise for a total of $2,000 awarded monthly.

Jake Q Music makes a debut appearance on The Friar Tuck stage with a high energy Guitar Rock Show highlighting British Invasion and Americana favorites from the 60s through the 90s. Expect sing along moments with songs by The Beatles, Yardbirds, Stones, CCR, Oasis, Eagles, Aerosmith, Billy Joel, and others. Known across Central Florida for lively vocal and guitar performances that have entertained thousands, Jake Q blends broad musical knowledge with creative flair to connect with audiences and turn the room into a celebration. Food and drinks are available at the pub to complement the live music.

Horror House Haunted House presents a circus-themed fright experience spread across more than 4,000 square feet on two levels. Explore scare zones, catch live performances and other shows, and hear rock bands perform. Between scares, play carnival games and grab bites from food trucks. Billed as the most expansive and darkest season yet, the big top transforms into a maze of thrills and chills.

Enjoy live music on the patio featuring About Tuesday.

A group bike ride rolls out from Trek Clermont with a route chosen by the riders. Plan for about two and a half hours on the bike, covering roughly 26 to 33 miles with a mix of climbs, flat sections, and stretches on public roads. The average pace is around 19 mph, and the group stays together rather than dropping riders. Keith leads the ride. Participants must follow traffic laws and ride at their own risk. Helmets are required, and lights are encouraged.

Embrace the season with a fall-themed SUP flow at Lake Hiawatha Preserve in Clermont, featuring a 90 minute session on Lake Minneola. Start with an easy paddle out to anchored spots, then enjoy the class on the water. Beginners are welcome, and comfort with swimming is encouraged. Bring seasonal accessories and decorate your board to keep the festive spirit going. You can bring your own or take advantage of available rentals. Registration details are provided through the event page.

A community plant exchange in the South Lake area where participants bring plants or items related to plants to swap with others or give away.

In the heart of Downtown Clermont, the Harvest Festival brings a festive Halloween celebration, hosted by Clermont Main Street and presented by Orlando Health South Lake Hospital. Explore more than 100 artisan vendors, enjoy live music and food trucks, and let kids have fun in a dedicated Kid Zone with family activities. A costume contest is open to both people and pets, rounding out a full day of fall shopping and community spirit.

The Promenade at Sunset Walk presents the Weekend Wellness Series featuring a free fitness class. A DJ provides music leading up to the workout, throughout the session, and after it wraps. Food and drink options are available nearby, including 7 Brew Coffee and La Boom Café. Participants in the Weekend Wellness Series receive 15 percent off the entire bill at Lizzie’s Memphis Style BBQ, along with a complimentary coffee with each entrée. Gift card drawings add an extra perk. Please bring a mat or towel. To qualify for the weekly gift card giveaway, an RSVP is required and you must be present to win.

A nostalgic Saturday tradition in Old Town brings classic car enthusiasts together for a weekly showcase that has delighted Central Florida for more than three decades. Show-quality vehicles from 1985 and earlier, including hot rods, street rods, and antiques, are welcomed to display, and a cruise invites all registered cars to take part. Admission is free for those showing cars and free for spectators, creating an easygoing outing for families of every generation. Participants bringing a classic should enter Old Town from Highway 192 beneath the east side of the Jukebox signs, where event staff will greet arrivals and arrange a security escort along the brick streets. Please do not drive on the bricks unless instructed. Cruisers can also enter a monthly giveaway totaling 2,000 dollars, with 1,000 dollars awarded on Friday and 1,000 dollars on Saturday. Each time a car cruises on those days during the month, an entry is earned. After the final Friday and Saturday cruises of the month, one name is drawn each day for 1,000 dollars courtesy of Old Town Kissimmee.

Enjoy a nighttime 5K run and walk with several interactive scare zones along the route. Costumes are encouraged, and top looks across multiple categories will receive prizes that include cash and merchandise.

Stevie G returns to The Friar Tuck for a Halloween show featuring an entire Elvis set alongside a broad repertoire of more than 250 songs that span Rat Pack and swing, rock and roll, British Invasion and contemporary music. With many years of performing experience in Florida and the UK, he delivers a varied program suited to the occasion. Costumes are encouraged, and there is no cover or ticket charge. These performances are typically busy and the reservation list is filling quickly, so reserving a table in advance is recommended by contacting the venue.

Horizon West Cars & Coffee is a relaxed community meetup held in the parking lot behind Agave Bandido. Owners and enthusiasts are welcome to bring cars or trucks of any year, make, or model and enjoy coffee and conversation with neighbors. The gathering is family friendly and focused on safety. Please avoid revving, burnouts, speeding, and racing so everyone can have a pleasant experience. This is an informal, recurring event where people share their passion for vehicles and connect with the local community. Attendance is at your own risk, and the organizers, property owners, sponsors, and vendors are not responsible for any damage, loss, or injury.

Each Sunday, the Downtown Clermont Farmers Market fills the heart of town with fresh produce, handmade goods, and a variety of local vendors. Visitors can pick up a coffee, enjoy a relaxed walk through the park, and browse at their own pace while supporting small businesses. It offers a welcoming, small town atmosphere for families and friends who want to make shopping local part of their weekly routine.

Enjoy a soothing art class with clear, sequential guidance from a professional artist. All materials are provided, along with an apron or smock, so you can relax and create. New techniques are explored each month, and beginners are welcome with no prior experience needed.

The Viceroy Curry Club brings Curry Night to The Friar Tuck with guest chef Poppadom Paul, winner of the Clermont Sun’s 2026 Reader’s Choice Award for Best Chef, presenting his renowned British curry from London. The menu moves from mild to fiery with Chicken Korma, Chicken Tikka Massalla, Chicken Pathia, Bengali Chicken, Chilli Chicken Massalla, Chicken Vindaloo, and the Bonfire Curry as the hottest choice. Every curry is served with pilau rice, a vegetable samosa, onion bhajee, Bombay potato, and a choice of garlic or plain naan. Each dish can be prepared with chicken, prawn, lamb, or a vegetable option. Plates are $25, with a $2 supplement for lamb. Pre orders can be made by messaging The Friar Tuck on Facebook or by asking a server.

Spend an evening savoring food tastings from over 60 local restaurants and businesses. Explore a wide mix of flavors in one outing and discover new favorites along the way.

Created for adults 55 and older, this Senior Expo at Lake Eva Event Center brings together local businesses and community organizations to showcase services and programs for older adults. Attendees can meet one-on-one with representatives, ask questions, and pick up complimentary items. Features include vendor booths, raffle drawings, health screenings, giveaways, and more. Walgreens will provide flu shots at an offsite clinic. Admission is free. Presented by Haines City and Miracle Toyota, with support from sponsors including Miracle Toyota - Haines City, IMA Medical Group, CarePlus - Humana, AdventHealth - Heart of Florida, Duke Energy, Valora Medical Group, Soni Family Practice, and Eye Specialists of Mid-Florida.

Designed for homeschoolers, this educational matinee at Medieval Times Orlando turns the Middle Ages into a hands-on learning experience. Students explore the Code of Chivalry with a live presentation that emphasizes citizenship, justice, respect, and forgiveness, then watch history come alive through demonstrations of swordplay, jousting, horsemanship, falconry, and introductory knight training. The program includes a visit to the Hall of Arms museum, where coats of arms, period weapons, and other artifacts are on display. An immersive tournament show runs for about an hour and a half, with a period inspired meal served during the action. Every student receives a cheering banner in the color of their knight, and complete lesson plans are provided for both before and after the visit to extend learning at home. Tuition is $54 for ages 4 through adult, and children ages 0 to 3 are free when seated on a parent’s lap. This is not a drop off program and at least one parent must accompany their child. For families using Step Up for Students, tuition for ages 4 and up is $49, with a separate $5 meal charge paid by parents. The program is approved for direct pay through Step Up for Students in Florida and may qualify for other school voucher programs. Parents are responsible for all food, transportation, and hotel costs, which cannot be covered by scholarship funds, and no refunds are issued under SUFS policy.

Returning for a second year to London Island, this permaculture convergence unfolds across 350 acres just south of Poinciana, next to Disney conservation land and Lake Hatchineha. The weekend format remains familiar, with a Friday potluck paired with micro-talks, a Saturday focused on the Earthskills Village and a lively trade blanket, and a Sunday of plant walks and talks. Meals highlight a blend of wild and cultivated foods gathered from the site and community contributions. Attendees can explore talks and hands-on sessions on fermenting, foraging, growing food, creating herbal medicines, natural navigation, agroforestry systems, water filtration, bamboo building, and more. The kids program expands under the guidance of the team from Creation Village World School, featuring immersive classes that use natural materials. Music and yoga round out the experience, and the famous trade blanket returns. For schedules and presenter announcements, look to social media updates.

Enjoy The New Collective performing live on the patio in an open-air setting.

A free community fair offers families and early childhood educators practical support for a smooth transition into kindergarten. Families can connect with local organizations and find guidance on readiness skills, developmental milestones, early childhood services, community programs, and educational materials. Educators can meet community partners and explore resources for kindergarten transitions, instructional strategies, classroom materials, and tools that link families to community supports. Confirmed partners include Family Network on Disabilities, Help Me Grow and Heart of Florida United Way, Park Place Behavioral, Osceola Library System, R.I.S.E. Up Osceola, and the Florida Department of Education Division of Early Learning. Educational materials and resources will be available for families and educators while supplies last. Support comes from Lakeshore, FLAEYC, BJ’s Wholesale Club, Teaching Strategies, and Discount School Supply. Separate registration is available for families and for educators.

This officially sanctioned tournament series takes place each year across more than 20 locations. Thousands of players converge for fast paced matches as they compete for appealing prizes and the chance to secure an invitation to the World Finals. Parking costs $15.

Discover the Saturday edition of the Kissimmee Home & Holiday Market, a marketplace centered on home and holiday themes. It takes place at the Events Center inside Osceola Heritage Park in Kissimmee.

Downtown Haines City transforms into a festive fall market filled with local flavor. Small business vendors feature tasty treats, handmade crafts, one of a kind gifts, and other goodies. A small pumpkin patch with a photo area offers a cheerful backdrop for autumn snapshots. The setting is family friendly and pet friendly, welcoming visitors of all ages. A bake off may be part of the festivities, with bakers potentially sharing their best creations and attendees possibly tasting, voting, and cheering for a winner. The market offers a relaxed stroll, plenty of seasonal atmosphere, and chances to support neighborhood makers.

Meet a few of The Animal League’s adoptable dogs at the brand new Petco in Clermont. Volunteers will be available to discuss adopting, volunteering, fostering and donating, and to answer questions about the organization. The Animal League follows a best match adoption process, with an application as the first step. Cats are also housed at this Petco, and Team Meow volunteers host on-site meet and greets. To spend time with a cat at the store, coordinate an appointment with the adoption team.

Experience a second annual superhero 5K paired with a Family Fun Night at the Highlander Building in Clermont, FL. The 5K is professionally timed, and each registration includes a T-shirt and medal. Every sign-up helps cover the copay for one therapy session for a child with special needs. The free family festivities feature local vendors and businesses, food trucks, bounce houses, games, raffles, dance parties, and other activities.

An Art Deco inspired evening blends vintage glamour with a meaningful mission. Attendees are invited to dress in black tie or 1920s Gatsby style, leaning into gold and black hues, sparkling details, and classic silhouettes. The night features fine wine and craft cocktails, a full dinner with hors d’oeuvres, and a special auction. The highlight is a lively ballroom competition with eight performers, with audience votes determining the winner. Proceeds benefit programs for local families experiencing homelessness, supporting housing solutions, job placement and skills training, emergency food assistance, and faith-based services that help individuals and families rebuild. For sponsorship information, contact New Beginnings leadership at 352-404-6946.

Hosted at Clermont City Center, the Pastor Appreciation Gala honors Elder James and Lady Sandra Rodgers with an evening centered on gratitude, fellowship, and thanks for their steadfast leadership, care, and service. The gathering brings together church family, friends, and the wider community to celebrate their impact. Attire is formal or semi-formal. Tickets are $60 per person. For ticket details, contact committee members: Bro. Clyde Mitchell, Missionary Torsha Durham at 305-401-4269, Evangelist Aundra Brodus at 352-874-2406, or Sis. Kiovonne Darby at 786-394-3173. The spirit of the event reflects the message of Jeremiah 3:15 about shepherds after God’s heart.

Explore a seven acre landscape at Here On The Farm with a guided look at 15 experimental gardens and diverse growing spaces. The route moves through vegetables, herbs and tea plantings, a Monet inspired area and shaded beds, a food forest, orchard and vineyard, pineapple and watermelon patches, wild blackberry brambles, a row of sugar cane, and a living bamboo fence. Along the way, the tour highlights sustainability in action, featuring a farmhouse designed for passive heating and cooling, rainwater harvesting, greywater filtration, a solar array, worm tea production, beehives, and erosion control supported by a lemongrass lined driveway, all rooted in regenerative farming practices. Farmer Banks leads with practical insights, stories, and a touch of dad humor. At times, locally known farmers stop in to share updates on new varieties and planting techniques. Seasonal tastings are part of the experience, so an appetite is welcome. Families are encouraged to attend, and participants may want a hat and plenty of curiosity.

Fairy Hair will be offered at The Summit of Winter Garden, a resort-style 55-plus community, on the second Monday of each month. Please check in at the front desk kiosk upon arrival. Friends and family are welcome. Appointments are optional, and you can text Tiana at (407) 864-7075 if you would like to schedule one.

Help Me Grow hosts a free Books, Balls & Blocks developmental screening at the West Osceola Library. Families can explore open play stations with books, balls, blocks, and other hands-on activities while learning about their child’s development. As children play and discover, parents complete a developmental milestones questionnaire. The screening is simple and low pressure, helping celebrate strengths, track progress, and highlight areas where extra support might be helpful. No appointment is required, and walk-ins are welcome.

Osceola County’s Healthy Senior Initiatives are open to residents ages 55 and older at the Roberto Guevara Community Center, offering two free activities that support well-being and social connection. The program includes Bingo, a lighthearted social game with friendly competition, and Sit & Be Fit, a seated, low impact class that focuses on strength, flexibility, balance, and overall wellness. Both activities take place twice each month throughout the year and are free for Osceola County residents.

Explore how to create a Florida-Friendly garden that appeals to sight, sound, smell, and touch at this Lunch & Learn workshop presented by UF/IFAS Extension Polk County and Haines City Water Utilities. Learn the fundamentals of Florida-Friendly Landscaping principles, discover plants with colorful blooms, inviting fragrance, textured foliage, and graceful movement in the breeze, and gather practical tips for designing a low-maintenance, sensory-rich landscape suited to central Florida yards. Registration is recommended and seating is limited. Lunch is provided for those who pre-register for in-person attendance, while later registrants may attend but might not receive lunch. Requests for accommodations are encouraged as early as possible, ideally at least ten days in advance. Programs may be canceled if minimum enrollment is not met, with updates shared via Eventbrite and by email to registrants.

At Railroad Park in downtown Haines City, this ceremony honors the bravery and sacrifice of U.S. veterans. Sponsors include The Cassidy Organization, AdventHealth - Heart of Florida, Duke Energy, and Eye Specialists of Mid-Florida.

Roll up your sleeves for a welcoming pasta making class at Erika's Tea Room & Gifts in Clermont, FL. Discover straightforward, authentic techniques to create fresh pasta dough from scratch, then roll and shape it into fettuccine, ravioli, and rustic hand rolled cuts. Round out the experience by crafting a signature sauce to match your pasta, and sip tea in a cozy tearoom setting filled with learning and laughter.

Hosted by Pete Prieto, this acoustic open mic creates a relaxed night of local music with sound kept gentle. Musicians can bring acoustic guitars or hand percussion, sign up, and share a few songs. Amps and full drum kits are not part of this event. Performers of all genres are welcome to play originals or covers. Food and drinks are available from The Friar Tuck.

The East Ridge High School Theatre Department presents A Knight of Theatre, a fall musical cabaret featuring the one act musical I Love You, You’re Perfect, Now Change alongside additional musical numbers. Rehearsals are underway to bring a lively mix of songs and scenes to the stage. Tickets are available.

Marking its twentieth year, the SUSC Soccer Competition highlights a legacy of faith, competitive play, and fellowship. This milestone gathering honors a long-running tradition of coming together around the game and the shared values that have sustained it.

Blazing Sands performs live on the patio, bringing music to an open-air setting.

The Last Territory is back at Sun On The Beach in Old Town for the next Conquer Kissimmee installment featuring professional wrestling. Food and drinks are available while the action unfolds. It is billed as the biggest party in Central Florida.

An all-new 5K is launching next year, with arrangements currently being finalized. The goal is to make it a recurring tradition during Veterans Day weekend. Participants can secure a spot through advance pre-registration, with an early bird option available.

The 15th Annual Help Keep Kids off the Street Charity Walk brings the community together at Kissimmee Lakefront Park to support Christ-centered programs and services focused on keeping youth safe and engaged. Participation is free, and each mile walked contributes to the cause. Expect a family friendly atmosphere with yard games, opportunities for children to explore police vehicles and a fire truck, and a variety of vendors and community partners. Raffle giveaways will offer thousands of dollars in prizes, and the first 700 registered walkers will receive complimentary food and drinks. Last year, the event returned more than $30,000 in donations from over 135 local attractions, businesses, and restaurant sponsors, including three kids bikes from Napleton Kissimmee, grand prize weekend getaway packages for youth and adults, and a $500 higher learning scholarship.

A full day of complimentary live performances awaits at the Embrace of Celebration music festival, with 15 bands and artists appearing across two stages for continuous entertainment. This all-ages community gathering spotlights local talent and features food and drink vendors with an emphasis on area businesses. Organized by Embrace of Celebration, a nonprofit charitable organization, admission is free. Proceeds from donations, sponsorships, and sales of food and merchandise support the organization’s mission to strengthen the community and build connections through the arts. Set in Celebration, Florida, the focus is on music, community, and connection.

A morning gathering at the Celebration Memorial Garden centers on honoring and remembering the lives of those who have touched many hearts. Participants can reflect together and remember loved ones. An RSVP is requested in advance.

This event blends a murder mystery with rounds of bingo. It features a three-course luncheon with three teas, and bingo for prizes takes place while the mystery is solved.

Sun on the Beach in Kissimmee hosts a high-energy spin on bingo that feels more like a party than a game. Get ready for big singalongs, dancing right at your table, playful chaos, over-the-top prizes, potent drinks, and a crowd that cranks up the volume. One moment you might be quietly checking your card, the next you could be cheering as someone scores a win while the music keeps everyone moving. This lively takeover pops up on the second Saturday of each month.

This free live music showcase at Lakeside Park features a premium, customizable band that can range from three to fourteen performers. The evening spotlights up-tempo sets built for the dance floor and includes a behind-the-scenes look at rehearsal. Attendees can sample a variety of musical styles and ensemble sizes, and there is an opportunity to speak with a producer about booking options for weddings, festivals, corporate events, and private celebrations. The musicians are specialists in live entertainment and are adept at getting the party started, with an energetic approach that keeps crowds moving.

BCe and friends are invited to take part in the Horrible Hundred ride in Clermont, Florida. This annual event usually falls around mid-November, and the planned day is tentative. Details will be updated once the organizers publish the 2026 schedule.

SparkleSilk teams up with Scates Realty and Pink Door Management for Pop in the Pink Door, a once-a-month chance to see Tiana for sparkles inside Flamingo Hall at Scates Realty’s new office in downtown Clermont.

The Celebration Women's Club presents the 2nd Annual Celebrachocolicious Chocolate Adventure, featuring a chocolate-themed route around Celebration guided by an event passport. Participants have a chance to win the Golden Ticket prize, and proceeds support music, drama, and visual arts programs at Celebration schools. The previous year’s event funded a $10,000 donation to these programs, with a goal of an even bigger impact this year. Tickets are available until sold out.

A casual in-person meetup brings together small business owners and nonprofit leaders to connect over coffee at Panera Bread in Clermont. Participants can chat, share ideas, and grow their networks in a relaxed, friendly atmosphere. It is a space for exchanging tips, supporting one another’s growth, and meeting like-minded people. Look forward to conversations and opportunities to build new connections and friendships.

Hosted by the School District of Osceola County, Choice Fair 2026 celebrates innovative learning, expanded options, and student achievement. Families can explore district offerings that include academic programs, career pathways, magnet options, and extracurricular activities. School representatives will be available to share details, answer questions, and help match students with opportunities that align with their goals. Highlights include the opening of the 2027 to 2028 School Choice and Magnet application. The fair also features student performances and art exhibits that spotlight local talent, health screenings, interactive booths from Osceola schools, and family-friendly activities with giveaways.

Ancient Sun performs live on the patio in Kissimmee, Florida.

After a fun outing last year, this Moana-themed paddle returns to Park of Indian Hills with music from the film setting the vibe. It is a free, BYOB event, and paddle board rentals are available for anyone who needs one.

Aquarelle Kids Academy presents The Nutcracker Remix, a student-centered performance at the Clermont Performing Arts Center. Young artists take the stage to share what they have been honing in Performing Arts classes, featuring music, dance, tumbling, and musical theater. The program celebrates their progress, showcasing growing confidence, creativity, coordination, discipline, and expressive skills as they bring their learning to life.

Downtown Clermont transforms into a festive winter scene for Clermont Celebrates, a cherished community tradition presented by AdventHealth. The event features snow, a visit from Santa, live music, a Kid Zone, and local vendors for seasonal shopping. It welcomes all ages and brings holiday magic to the center of Downtown Clermont.

Lake County Comic Convention returns for its sixth year with a full day devoted to comics, anime, gaming, and pop culture at the Clermont Performing Arts Center in Clermont, Florida. Attendees can show off cosplay, meet talented artists and writers, and hunt for exclusive merchandise and collectibles. Whether a dedicated collector or new to the scene, there is plenty to explore in this fan-focused celebration.

Coach Diane Calloway, known as TRiDi, leads structured training sessions focused on pace work, pick-ups, and speed work at Clermont Waterfront Park in Clermont, FL. Each workout is designed to accommodate athletes of all paces. Meet by the boat ramp restrooms located just east of the park. Please bring hydration, a stretch band, and a towel.

Celebrate Thanksgiving with a festive 5K at picturesque Waterfront Park. Whether aiming to run your fastest, enjoy a relaxed walk, or keep an easy holiday pace, this event welcomes all levels. Registration includes chip timing, a turkey-themed finisher medal, a soft ring-spun cotton short-sleeve shirt, awards by age group, and complimentary photos. Race day packet pickup will be available at the park before the start. Create a new holiday tradition with a scenic course and plenty of seasonal spirit.

Rooted in a spirit of community, compassion, and generosity, this nonprofit cattle show at the Kissimmee Livestock Pavilion provides support to families dealing with sudden hardships. Over the years it has grown from a cattle show into a tradition that brings together exhibitors, sponsors, and the local community to create meaningful help when it is needed most. Expect cattle show competitions, custom championship buckles, a silent auction with additional fundraising opportunities, and vendors, all focused on aiding a family in need. The event continues to grow while staying true to the purpose at its core.

Enjoy live music on the patio featuring The Rundown.

Meet adoptable cats from The Animal League at the new Petco Clermont. Team Meow volunteers will be on site for friendly meet and greets and to share information about becoming a foster. The Animal League follows a best match adoption process that begins with an application. Cats housed at Petco Clermont can be viewed during store hours, but Petco employees cannot facilitate petting or holding. To arrange an in-person meeting with a specific cat, contact The Animal League’s adoption team to set an appointment.

This no-cost workshop focuses on practical ways to care for both mind and body. It features gentle, beginner-friendly stretch yoga with guided meditation, straightforward mindfulness practices to help steady thoughts and emotions, and creative, hands-on art activities. There is also time for conversation and connection among people who share an interest in art and mental health. By highlighting self-care and mental health awareness, the gathering aims to strengthen community well-being and offer support to individuals experiencing significant challenges related to life-altering circumstances.

The first annual Solivita Toys For Tots golf tournament will be held at Stonegate Golf Club in Solivita. Participants can look forward to swag bags plus lunch with beer and water provided. The winning team takes home a $500 prize, and there are two $10,000 hole-in-one contests, along with other perks. Registration is open, and sponsors are welcome, with recognition planned on tournament day and again the next day at a concert and toy drive.

Trashy Annie fires up unfiltered rock and roll made for live stages and late nights, with towering guitars and hard-driving rhythms that land strongest on stage. Led by Annie Davis, the 2023 CMA of Texas Americana Artist of the Year and a Survivor Season 49 alum, the band delivers a high-energy set that is raw, sweaty, and fully committed. Nothing glossy, nothing extra, just pure rock and roll at Meliá Orlando Celebration for Celebrity Weekend.

The Grinch appears at Books-A-Million for a special visit featuring story time, a meet and greet, a photo opportunity, and a chance to have a book signed. The featured reading is How the Grinch Stole Christmas...According to Max, a retelling that shares the events of Christmas Eve from Max’s point of view, with the loyal sidekick taking the lead. An Eventbrite ticket includes admission for your family, one copy of the book, and a photo op with the Grinch. Only one RSVP is needed per family. Additional copies can be added during ticket purchase, and books will also be available in store while supplies last. Space is limited, and RSVPs are handled through Eventbrite.

Women come together for a cozy holiday ornament exchange that blends lighthearted conversation with heartfelt connection. The atmosphere is welcoming for those attending solo, making it easy to meet new friends and share the spirit of the season. Look forward to laughter, genuine community, and a warm, festive gathering.

At Old Town, a festive toy drive gathers donations to brighten the season for children across Osceola County. New, unwrapped toys are collected during the Friday and Saturday night car shows and cruise, and Santa with his holiday helpers will be on site to greet attendees and receive donations. All toys and monetary contributions go to the Osceola Council on Aging, keeping the impact local for families. Coins gathered from the fountains along the Brick Streets, including the Old Town fountain, also support the effort by funding additional toys and gifts. Expect a cheerful holiday scene with lights and car shows illuminated for the season, all focused on making a difference close to home.

Step into a luau dinner show where wizarding whimsy meets island style. Creative attire is encouraged, whether that means a tropical spin on beloved witches and wizards, Hogwarts house colors reimagined with Hawaiian flair, outfits inspired by the mysterious denizens of the Black Lake, island looks nodding to fantastic beasts, or an original magical tropical ensemble of your own design. Seating options include premium and standard levels. Premium seating is priced at $79.99 for adults and $39.99 for children, with ages 2 and under admitted at no charge with a paying adult. Standard seating is $69.99 for adults and $29.99 for children ages 3 to 12, with ages 2 and under free with a paying adult. Use promo code DIRECT to take $10 off. Interest has leaned toward premium seating, though the choice is entirely up to each party. The buffet features Polynesian chicken, kalua pork, baked salmon, beef meatballs, vegetarian lo mein, fried rice, macaroni salad, fresh fruit, steamed vegetables, fresh tossed salad, krab salad, dinner rolls, and assorted desserts. Tea, water, and Coca-Cola products are included, and a cash bar will be available. Dietary needs are taken into consideration and the menu is subject to change. Advance notice of allergies or special diets helps the venue prepare. Current indicators note gluten free options and information regarding dairy, eggs, fish, wheat, and pineapple, along with selections that avoid peanuts.

Before the weekly Car Cruise, residents from Sherwood Forest RV Resort bring out their personal golf carts, each trimmed with seasonal lights and decorations, for a festive roll through Old Town. The carts arrive and parade down Main Street ahead of the Car Cruise, creating a bright showcase of holiday spirit.

Spend the afternoon playing bingo, enjoying prizes, sharing laughs, and connecting with fellow Osceola County residents ages 55 and up. The event takes place at Hart Memorial Central Library, second floor. Expect rounds of bingo, prizes to win, and plenty of friendly conversation in a relaxed setting.

Hands of Hope America is creating a North Pole themed evening that celebrates hope and community. Families can look forward to holiday lights, cheerful activities, and moments made for smiles and memories. The plan includes interactive, Christmas themed stations hosted by community partners, with a goal of engaging 25 organizations to help shape a night filled with joy, love, and encouragement. More than a seasonal celebration, this gathering emphasizes giving back and showing families that they are seen, supported, and valued.

Now in its fourth year, this holiday fest offers a choose-your-distance bike ride or walk on the Clermont Bike/Walking Trail at Waterfront Park. Cyclists register for $25, and walkers participate for free with fundraising encouraged to benefit the Bleeding Disorders Foundation of Florida. Raise at least $25 to receive an event T-shirt. Form a team to boost your fundraising, with more prizes available as totals grow.

The #SLAPPERS team will take on 70.3 Florida in Haines City. This team event centers on training together, support from coaches, and racing to earn TriClub points toward the trophy.

Osceola Magic faces the Oklahoma City Blue at Osceola Heritage Park in Kissimmee, FL. Guests aged two and older need a ticket to attend. For suite inquiries, contact 407-447-2140.

SparkleSilk partners with Scates Realty and Pink Door Management for a monthly Pop in the Pink Door visit in the Flamingo Hall at Scates Realty’s new downtown Clermont office. Stop in to see Tiana for sparkles.

Celebrate the season and kick off Winter Break with a festive paddle on the water. This free, BYOB outing offers paddle board rentals for anyone who needs one.

Enjoy a festive nighttime 5K run or walk weaving through Historic Downtown Clermont and along the waterfront. Finishers receive a medal and a long sleeve shirt, and results are chip timed. Look for glow necklaces, prizes for creative costumes, and a sweet finish with hot chocolate and cookies.

Registration is open for a Generation Cup qualifier featuring a two-person format that combines modified best ball and scramble play. Teams compete in three divisions, with pairings of grandparent and grandchild, parent and child or an aunt or uncle with a niece or nephew, and a PGA Professional with a generational family member. A USGA handicap is required. The top gross and net teams from each division advance to the National Championship. Entry is $250 per team for Omni club members and PGA Professionals and $350 per team for all other entrants. The fee includes lunch, awards, green fee, and range usage on the competition day. Capacity is limited, so early registration is recommended. Competition takes place on the National Course.

Ring in the new year with a festive 5k run and walk at Shingle Creek Regional Park in Kissimmee, Florida. Participants can run, walk, or simply enjoy the post-race beer. The event is chip timed and professionally scored by J3 Timing, with results available online. Registration includes a short sleeve super soft ring spun cotton T-shirt, a finisher medal, a race bib for the chip timed 5k, and a beer after the finish.

This event features fiber-focused activities and fun, with further details to be announced soon.

Rising Tides II brings together classes and coaching sessions, sparring, and additional activities at Clermont City Center in Clermont, FL. The instructor lineup features Jake Pendergraft covering rapier and sidesword, Brad Cramer Jr focusing on Italian sabre, lan Marra presenting Harnis (Armored), Connor Gibson on spada due mani, and Jack Murray teaching rapier. Further information will be shared as it becomes available, and tickets are on sale.