Events in Kissimmee, FL

At the Orlando Tattoo Show, artists from the United States and overseas gather for a lively, three-day celebration of tattoo art, culture, and creativity. The event welcomes working artists, passionate fans, and the simply curious to meet creators, find emerging talent, and see the latest styles in body art. Parking costs $15.

Sun on the Beach in Old Town welcomes the return of The Last Territory with another Conquer Kissimmee installment. Professional wrestling takes center stage alongside food and drinks for a party-style atmosphere in Central Florida.

This group hike at Disney Wilderness Preserve brings everyone together at the start and keeps the group together through the finish. The route spans about 6 miles round trip on easy terrain. For more information, contact the host.

Learn the craft of Chicago-style deep dish at UNO Pizzeria and Grill in a hands-on cooking class. Work alongside the restaurant’s chefs to mix and press the signature crust, build the layers of cheese, toppings, and sauce, then bake it to a golden finish. The session welcomes all experience levels, from first-time cooks to devoted pizza fans. Each ticket includes a step-by-step demonstration, lunch with salad and a beverage, plus unlimited soft drinks.

The Bingo Experience turns Sun On The Beach into a high-energy spin on classic bingo, packed with singalong moments, dancing right at the tables, off-the-wall antics, outrageous prizes, and cocktails with a serious punch. The crowd brings concert-level volume, so a quiet card can quickly become a full-on celebration when someone wins. This lively takeover has become a monthly tradition on the second Saturday, delivering big laughs, bold drinks, and bingo chaos all in one place.

Taking place at Half Barrel Beer Project, this gathering centers on round 16 of the 2026 Formula 1 season, the Spanish Grand Prix. The event is open to everyone.

Support Orlando City B as the team continues its 2026 MLS NEXT Pro season. This event highlights fans rallying behind the club throughout its league campaign.

Orlando City B faces Toronto FC II under the lights at Osceola County Stadium at Osceola Heritage Park in Kissimmee. This MLS NEXT Pro matchup highlights emerging talent, tactical experimentation, and high-energy play, with the potential for unpredictable moments from the opening whistle to stoppage time. The environment offers a close view of the next wave of players competing at a high level.

Metamorphosis partners with Half Barrel Beer Project to present a hands-on charcuterie workshop where creativity meets flavor. Learn how to build a beautiful, delicious board, including how to craft a Provolone Rose, design a Salami River, and refine fruit and cheese cutting. Instruction covers placement, balance, and arrangement so every element looks and tastes its best. All materials and ingredients are provided, and everyone leaves with a charcuterie creation to enjoy. Participants receive 15% off food and beverages from Half Barrel Beer Project the night of the workshop. A special rate is available at $40 per person when paying via Venmo, CashApp, or Zelle, $41.40 per person via credit card with advance notice, and $47.87 per person through Eventbrite. Seats are limited, registrations are final and non-refundable, and advance tickets are required. For questions, contact Metamorphosis at 407.719.1865. Payments can be sent to Venmo @ButterflyDreamsMetamorphosis, CashApp $BDMeta, or Zelle 407.719.1865.

Celebration hosts a Health and Wellness Expo, a Celebration Town Hall event presented by Experience Kissimmee. This community-focused gathering promotes healthy living through educational booths, live fitness demonstrations, activities for kids, food trucks, and a live DJ. Guests can explore local health and wellness resources and connect with organizations dedicated to well-being.

This two day Kissimmee expo centers on reptiles and exotic animals, showcasing live species from many parts of the world. Meet knowledgeable vendors, ask questions, and purchase pets and related supplies directly from the experts while learning more about these fascinating creatures. Parking is $15.

At Hilton Orlando, the Headdress Gala is a long-running Orlando charity celebration where creativity and impact meet. The production showcases large-scale staging, theatrical lighting, and standout moments from live performers such as singers, dancers, drag artists, aerialists, and acrobats. Fashion is central to the experience, highlighting headdresses, fascinators, statement pieces, and creative black-tie attire. Each ticket benefits Hope & Help, supporting HIV and STI prevention, testing, treatment, and healthcare for thousands across seven counties. Bold, festive, and full of energy, it brings bold fashion and live performance together in one memorable night.

Orlando City B takes on Atlanta at Osceola Heritage Park as part of the 2026 MLS NEXT Pro season.

Spend a day at Topgolf Orlando celebrating community and purpose with the third annual Drive for Dreamers. Participants can opt for a scramble-style competition by bay or choose a mix of playful mini-games, making it welcoming for both experienced golfers and first-timers. Expect engaging golf activities alongside interactive vendor experiences and friendly challenges, plus a menu that starts with a light breakfast and continues with a buffet lunch, all in support of programs that build a more inclusive community. The event supports Dreamplex programs that expand opportunities for people with disabilities and special needs of all ages, including therapy, education, adaptive sports, social activities, and vocational training, helping create pathways for everyone to thrive. For sponsorship information, contact Jennifer Buchanan at (954) 778-9177 or jbuchanan@cfldreamplex.com.

Celebrate the season at a fall-themed festival highlighting women in business. Browse a marketplace of women-owned brands, enjoy complimentary face painting, take photos in a booth, and take part in kid-friendly raffles at no cost. The first 10 guests receive goodie bags. A hands-on arts and crafts zone will be available, along with an outdoor playground and soft play. Admission and parking are free, offering a relaxed way to enjoy an afternoon of community, fun and autumn vibes. Organizers are also seeking local women-owned vendors interested in showcasing products, building brand awareness, and connecting with the community.

Channel your inner hero at Celebration Lakeside Park during a family friendly 5K that supports families affected by cancer. Now in its 10th year, the M Family Foundation presents the Superhero Race Against Cancer 5K to raise funds for ovarian cancer and pediatric brain cancer, including DIPG and DMG. Participants are encouraged to wear capes or superhero attire as they take part in a spirited run that brings awareness and hope to those facing these illnesses.

VetteFest returns to Old Town for the 21st annual celebration of the Corvette, bringing together vintage standouts and modern machines that showcase the power, curves, and unmistakable sound of this American icon. On-site registration is available, and the festivities include a Corvette-only cruise along Old Town’s main street. An event T-shirt will be offered for $15 while supplies last, with both cash and card payments accepted. Whether arriving with a car or coming to appreciate the lineup, the Corvette community gathers here in full force.

Day’s Trips presents a group outing to Boots, Bulls & Barrels at Silver Spurs Arena. The package is $80 and includes bus transportation departing PSL with a pickup in Vero Beach, direct travel to the Kissimmee venue, and gold level seating located across from the chute. The arena is indoors and climate controlled. Vendors sell food, beer, and souvenirs, and bringing cash is recommended. After the event, the bus returns home. Payment is due at booking. Tickets are nonrefundable but can be transferred to another person. 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, reference number ST44375.

At Rosen Shingle Creek in Orlando, the Harvest Ball edition of Arts for Carts offers a formal evening of dinner, dancing, and philanthropy that benefits the specially abled dogs cared for by LoveyLoaves, a 501(c)3 rescue in East Orlando devoted to saving and rehabilitating dogs facing challenges such as amputation, sensory impairment, complex medical needs, and illness or injury. The program features guest speaker Tamar Geller, a New York Times bestselling author and canine expert known for The Loved Dog method, shaped by her experience in Israeli Special Forces intelligence and by observing wolves in the wild. The night includes a live DJ, hors d’oeuvres and dinner prepared by Rosen Shingle Creek, a silent art auction, chances to meet LoveyLoaves dogs, and stories from the rescue. Autumn inspired formal attire is encouraged. Proceeds support LoveyLoaves medical and rehabilitation funds that provide mobility carts and veterinary care, and also advance the goal of acquiring land to develop a safe haven where dogs with special circumstances can receive rehabilitation and physical therapy, be rehomed or fostered, or live out their days in comfort.

At Celebration Brewing Company, Piano Rob leads an interactive, family-friendly piano request show where the audience shapes the setlist. Expect singalong moments spanning Disney favorites, Broadway tunes, and pop hits, with surprises sprinkled in. Admission is free, and the brewery serves food and drinks to enjoy during the music. A food or beverage purchase is required to secure a table.

A relaxed, connection-focused Disney getaway brings together adults, friends, partners, and children to rediscover a bit of magic at a comfortable pace. The trip begins with a short stay at Walt Disney World during EPCOT’s Food and Wine Festival, offering unhurried mornings, flavorful bites, meaningful conversation, and plenty of laughter with a dose of nostalgia. The adventure continues aboard the Disney Fantasy for a Disney Cruise Line sailing that features Halloween on the High Seas and visits to Castaway Cay and Lookout Cay at Lighthouse Point. The aim is simple... share good food, enjoy great conversations, soak up Disney magic, and build memories that turn new faces into new friends.

A gathering at Half Barrel Beer Project marks the eighteenth round of the 2026 Formula 1 season, the Singapore Grand Prix. The event is open to everyone.

This Halloween-themed pin trading event fills the full ballroom at Holiday Inn Resort Kissimmee by the Parks, with free parking available. Attendees can explore an education station, enjoy complimentary snacks, enter hourly raffles, and take part in a meet and greet with WDW Kevin. Traders are welcome to wear costumes to match the spooky theme. Admission is collected at the door by cash or PayPal, priced at $5 for adults and free for those 16 and under. By attending, participants consent to photography and video, and each person is responsible for their own transactions.

Hosted at Rosen Shingle Creek in Orlando, the Sit. Stay. Sparkle. Southeast Gala celebrates and supports a mission to provide expertly trained service dogs at no cost to adults, children, and veterans with disabilities. The evening features pre-dinner cocktails, a served dinner, and entertainment, along with a combination of live and silent auctions offering a handpicked selection of items. The program shares stories from clients about the life changing impact of their service dogs. Cocktail attire is requested.

Half Barrel Beer Project hosts a gathering centered on round 19 of the 2026 Formula 1 season, the United States Grand Prix. Everyone is welcome.

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.

Discover a Disney getaway built around the EPCOT International Food & Wine Festival, where global flavors, live entertainment, unique shopping, and the magic of Disney come together. The experience is centered at JW Marriott Orlando, Grande Lakes, combining resort comfort with a group travel vibe that keeps things easy from arrival to farewell. It is planned as a weekend focused on fun, food, fellowship, and lasting memories. Inclusions feature four nights at JW Marriott Orlando, Grande Lakes with daily gourmet breakfast, an exclusive welcome meet and greet, a ticket to the EPCOT International Food & Wine Festival, a premium outlet shopping experience, the Travel Addicts poolside experience, an evening at Disney Springs, and a signature farewell brunch. Guests receive a curated Disney gift bag and the support of a dedicated Melanin & Stamped hostess. Roundtrip charter bus transportation is available at an additional cost.

Designed for homeschool families, this hands-on Middle Ages unit study at Medieval Times Dinner & Tournament in Orlando turns history into a living lesson. An educational presentation explores the Code of Chivalry with themes of citizenship, justice, respect, and forgiveness. Students see demonstrations of swordplay, jousting, horsemanship, falconry, and knight training. The experience includes a tour of the Hall of Arms Museum with coats of arms, weaponry, and medieval artifacts. A one and a half hour tournament unfolds on stage while a period-style meal is served. Each student receives a cheering banner in their knight’s color, and complete lesson plans are provided for before and after the trip. 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, so at least one parent must attend with their child. For families using Step Up for Students, tuition for students age 4 and older is $49, with a separate $5 student meal charge paid by parents. The program is approved for direct pay through Step Up for Students in Florida and may qualify for other voucher programs. Parents cover all food, transportation, and hotel expenses using personal funds, and SUFS policy does not allow refunds.

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.

At Half Barrel Beer Project, round 21 of the 2026 Formula 1 season is in focus with the Brazilian Grand Prix. All are welcome.

An inaugural 5K is being organized with plans to make it a yearly tradition during Veterans Day weekend. Pre-registration is available, including a discounted early bird option. More details will be shared as arrangements are finalized.

Now in its 15th year, this community charity walk at downtown Kissimmee Lakefront Park rallies support for Christ centered programs that help keep kids off the street. There is no cost to participate, and each mile logged contributes to those services. Participants can enjoy chances to win raffle prizes totaling thousands of dollars, and the first 700 registered walkers receive complimentary food and beverages. Vendors and community partners will be on site with yard games, and children can explore police vehicles and a fire truck, making it a family friendly day. In the previous year, more than $30,000 in donations were given back to the community through contributions from over 135 local attractions, businesses, and restaurant sponsors, including three kids bikes from Napleton Kissimmee, weekend getaway packages for youth and adults, and a $500 higher learning scholarship. Organizers look forward to giving back even more this year as the community comes together to walk for children and safer streets.

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.

At The Rosen at Shingle Creek, The Health & Healing Expo by Documenting Hope offers a two-day immersive conference paired with an experiential expo focused on practical ways to restore and sustain vibrant health. The program reflects a growing movement to look beyond symptom management by addressing root causes, exploring the interplay of gut, brain, and immune function, considering environmental and lifestyle influences, and tailoring care through integrative, personalized approaches. Rather than piecing together information from many sources, participants can find these perspectives gathered in one place. Expect opportunities to learn directly from people working in these fields, see how different methods complement one another, and engage in conversations that go deeper than the basics. Professionals can discover new tools to enhance their practice, while parents and individuals can gain clarity and direction for next steps. For anyone navigating a complex wellness landscape, this setting offers a clear path to understanding and connection. Early-bird pricing is available for a limited time. Arrive curious and leave feeling more connected and informed.