Events in Osceola County, FL

St. Cloud Main Street’s guided walking tour winds through Downtown St. Cloud, blending local history with eerie folklore. A guide shares stories of the people and places that shaped the community, along with accounts of fires, tragedies, and curious happenings passed down through generations and retold by those who live or work in the historic buildings today. Along the way, hear about unexplained footsteps, doors that rattle on their own, mysterious figures, and other moments that defy easy explanation. This experience suits history lovers and paranormal enthusiasts alike, offering a fresh perspective on the area and its enduring legends. Tickets are $30 per person.

Old Town’s Bike Night brings Central Florida’s biker community together at the Old Town Entertainment District in Kissimmee for a free, biker-friendly gathering. All makes and models of touring motorcycles are welcome, including Harley, Indian, trikes, and slingshots, celebrating the brotherhood and sisterhood of riders and the unmistakable rumble through Old Town. Participants must have a valid driver’s license and proof of insurance. Colored patches are not permitted.

Celebrate the 2000s with a music bingo night built around the decade’s pop hits. Players listen to familiar tracks, mark their cards, and try to be the first to call bingo. It takes place at Pizza Hut in St. Cloud, Florida, with sing along moments and the option to enjoy pizza with friends.

Wojo’s Bar & Grill hosts a Scream themed trivia night focused on the horror film series. Participants tackle questions about Ghostface, the town of Woodsboro, memorable lines, surprise twists, and the franchise’s most chilling moments. Teams can put their knowledge to the test, and familiarity with classic horror survival rules may come in handy.

Tiny Tees offers a playful parent‑child introduction to golf where little ones build confidence, coordination, and friendships through age‑appropriate games, movement, and hands‑on activities. Designed for toddlers and preschoolers, it is especially welcoming to beginners and families seeking a positive first sports experience or a fun weekly activity together. Classes are led by Coach Roger, and a parent, grandparent, or trusted adult takes part alongside the child throughout. Young golfers pick up early skills with putt and chip challenges, movement‑based drills, rotating stations, and small team games while practicing balance, focus, listening, turn taking, teamwork, and on‑course safety and etiquette. The atmosphere is relaxed and encouraging, with plenty of celebration for effort and progress. Parent participation is required, and no prior golf experience is needed. Sessions take place at Royal St. Cloud Golf Links in St. Cloud, Florida. Enrollment is limited to eight parent‑child pairs per six‑week session. The fee is $199 per parent‑child pair for the full six sessions, and weekly activities are included. Bring your little golfer, a big smile, and a sense of adventure.

This afternoon social brings together a welcoming circle of women to play Hand, Foot and Toe at the Kissimmee Woman’s Club Clubhouse. The gathering is relaxed and community oriented, with conversation and laughter complementing the cards. It is held weekly. Players at any experience level are comfortable, and newcomers can learn the game from others at the table. Attendees may come on their own or with a friend. Participants may bring their lunch.

Step up to the mic at Old Town’s karaoke, where every performer takes the spotlight. Whether you are a seasoned singer or simply enjoy songs with friends, all experience levels are welcome. Take the stage on Old Town’s Main Stage next to Southern Breeze and share a favorite tune.

Designed for Osceola County residents ages 55 and up, this District 3 monthly bingo event at Poinciana Library in Kissimmee is hosted by Chairman Brandon Arrington. Expect a Fall Festival theme, prizes, and a friendly setting to meet neighbors and enjoy a few lively rounds.

Every Friday night at Old Town, a muscle car show welcomes show-quality vehicles and ends with a cruise for registered participants. Eligible entries include muscle cars from 1964 and newer, plus hot rods and classics from 1985 and earlier. There is no charge for car owners to participate, and the public can attend at no cost. Participating classic cars should enter at the east side beneath the Jukebox signs, where event staff will greet drivers and arrange a security escort along the brick streets. Please wait for permission before driving on the bricks. Old Town Cruisers earn an entry each time they cruise on Fridays and Saturdays during the month for a chance to win $1,000. One name is drawn after the final Friday and Saturday cruises each month, awarding a total of $2,000 monthly courtesy of Old Town Kissimmee.

Celebrate the season at the Fall Festival at Renaissance Academy of Arts and Sciences, where barbecue fare will be available for purchase.

ARTS Unlimited, LLC presents Night of the Living Dead Live, a comedic tribute to the landmark 1968 film that is officially approved for the stage. Six strangers barricade themselves in a creepy farmhouse while a swarm of zombies presses in, and the production digs into the movie’s core themes, the swinging 1960s atmosphere, and its lasting influence on horror. With more than one possible ending, the characters face a cascade of dilemmas and slapstick chaos as they struggle to make it through the night. Select performances also feature a costume contest. To take part, a ticket is required, costumes must be family friendly, faces must remain clearly visible without masks or heavy makeup, and weapons as well as any blood or gore are not allowed. Two winners are chosen at each participating show. Entry may be refused to anyone who does not follow these rules, and no refunds are issued if removal is required.

A Zumba fitness class that welcomes all fitness levels, offering a friendly environment and a fun workout.

The ballroom at Holiday Inn Resort Kissimmee by the Parks becomes a Halloween themed hub for pin fans, offering a full day dedicated to trading and community. Attendees can explore an education station, enjoy free snacks, take part in hourly raffles, and meet WDW Kevin. Costumes are welcome, and traders are encouraged to dress up for the festivities. Admission is $5 for adults and free for anyone 16 and under, payable in cash or via PayPal at the door. Free parking is available. By entering, guests consent to photo and video capture, and each person is responsible for their own transactions.

The Promenade at Sunset Walk hosts the Sunset Walk Weekend Wellness Series featuring a complimentary fitness class with a live DJ keeping the music going before, during, and after the session. Fuel up with food and drink selections from 7 Brew Coffee and La Boom Café. Participants receive 15% off their entire check at Lizzie’s Memphis Style BBQ and a complimentary coffee with each entrée. A weekly gift card giveaway adds extra fun. An RSVP is required to be eligible, and winners must be present to claim a prize. Please bring your own mat or towel.

This Halloween themed adoption event from The Way Station Cat & Kitten Rescue takes place at Petco Poinciana in Kissimmee. Attendees can meet adoptable cats and kittens, search for a perfect match, and maybe leave with a companion sweeter than any treat. The gathering welcomes those ready to adopt as well as supporters of rescue, with plenty of whiskers, purrs, and seasonal charm.

This family-friendly Halloween glow bingo gathering brings together kids, grandparents, extended family, and neighbors for a single-day celebration. It is a private, ticketed event, and entry is limited to guests with seats confirmed for every person in their party through Eventbrite.

A weekly Old Town tradition takes car enthusiasts on a trip down memory lane and has been part of the community for more than three decades. The showcase features show-quality vehicles from 1985 and earlier, including hot rods, street rods, and antiques. After the display, registered cars roll out together for a cruise. Admission is free for participants and free for the public, making it a family-friendly outing for every generation. Drivers bringing classic cars should enter beneath the east side of the Jukebox signs, where event staff will greet arrivals and arrange a security escort onto the brick streets. Please wait for permission before driving on the bricks. Old Town Cruisers also earn entries toward a $2,000 monthly giveaway. Each time you cruise on Friday and Saturday during the month, you receive an entry. One name is drawn after the last Friday cruise and another after the last Saturday cruise for $1,000 each courtesy of Old Town Kissimmee.

Wojo’s Sports Bar hosts a music-themed bingo night celebrating the legends of popular music. Mark your cards to familiar hits from major artists, sing along, and take your shot at bingo glory. Arrive early with friends to enjoy food, classic songs, and plenty of chances to win.

A weekly yoga class takes place at Basecamp. Participants should bring a yoga mat and plan to practice on the lawn by the yurts.

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.

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.

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 themed trivia night at Wojo’s Bar & Grill celebrates the Ghostbusters films, with questions spanning supernatural run-ins, ghostbusting gear, fan favorite characters, quotable lines, and standout scenes. Teams compete to show their knowledge in a lighthearted movie trivia setting.

Enjoy live music on the patio featuring About Tuesday.

Choose a favorite pumpkin from the patch, then carry it into the pasture with the goats to carve while these friendly companions wander nearby.

Wojo's Sports Bar hosts a Halloween-themed music bingo night filled with singalong favorites and seasonal hits. Mark off songs on your card as you recognize them and aim for a winning bingo. Enjoy a lighthearted evening of music, laughter, and friendly competition with a spooky twist.

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.

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.

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.

During the fall Citywide Garage Sale, residents within the city limits can host garage sales without the usual city permit. At other times, a permit is typically required and should be obtained through the city's standard permitting process.

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.

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.

Hosted by Toho Water Authority, AdventHealth, and the City of St. Cloud at St. Cloud Lakefront, this movie night features a screening of Zootopia 2. Enjoy a fun evening with complimentary popcorn for attendees. Bring something comfortable to sit on, such as a lawn chair or a blanket, and settle in for the film. There is no charge to attend.

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.

Experience a supportive health and wellness class tailored for older adults. The session focuses on practical ways to enhance strength, flexibility, balance, and overall well-being, with activities adapted for all fitness levels and an emphasis on safety and enjoyment. Whether the goal is to support independence, improve health, or simply add a little fun to the week, this program encourages staying active and engaged. Instruction is provided by Felicia Marable-Williams, Family and Consumer Sciences Agent with UF/IFAS Extension Osceola County. Please wear comfortable clothing and sneakers or other sturdy closed-toed shoes. A liability waiver will be provided at check-in and must be completed to participate. There is no fee to attend. Classes may be cancelled if minimum enrollment is not met, and registrants will receive notice by email. For disability accommodations, call 321-697-3000 at least 10 business days in advance. Inflammatory or inappropriate behavior will not be allowed, and disruptive participants may be removed. For more information, call 321-697-3000.

This guided walk through Downtown St. Cloud weaves together the city’s past with tales of lingering spirits passed down over generations and shared by people who live and work in its historic buildings. Participants visit notable landmarks while a guide recounts episodes of fires, tragedies, and curious happenings that shaped the community, along with firsthand reports of odd footsteps, rattling doors, mysterious figures, and other puzzles that defy easy explanation. It suits history lovers, paranormal fans, and anyone interested in seeing the area from a new perspective. Admission is $30 per person.

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.

Enjoy an outdoor showing of Wonka at Basecamp, where attendees can spread out on the lawn, snack on complimentary popcorn and chocolate coins, and sample offerings from local food trucks.

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

Celebrate the season with a cheerful evening of painting that gives back. Enjoy a relaxed, creative atmosphere as you paint and support a meaningful purpose.

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.

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.

Sunbridge’s annual Starry Night offers a festive tree lighting and an evening of seasonal activities for all ages. Families can visit with Santa and Mrs. Claus for photos and wish sharing. A holiday market features handcrafted gifts from local makers, and playful flurries of faux snow add to the atmosphere. Food trucks serve seasonal bites and sweet treats while live music and holiday performances set a cheerful mood. Children have a dedicated area with activities to keep them entertained. The celebration concludes with the lighting of the Sunbridge tree to welcome the start of the holiday season. Admission is free and open to the public.

Help Me Grow hosts a free Books, Balls & Blocks developmental screening at the Veterans Memorial St. Cloud Library. Families can enjoy an open play setting with books, balls, blocks, and other engaging activities while learning about early childhood development. As children explore, parents complete a brief developmental milestone questionnaire. This simple, stress free screening helps celebrate strengths, track growth, and highlight areas where additional support may be useful. No appointment is required and drop ins are welcome.

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.

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.

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.

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.