Events in Kissimmee today

Staying active and socially connected can support overall health, lift mood, and help maintain independence. Osceola County’s Healthy Senior Initiatives provide two free options each month for residents ages 55 and older at the Robert Guevara Community Center. Bingo offers a welcoming, social setting with plenty of laughs and friendly competition. Sit & Be Fit is a gentle, seated exercise class that helps build strength, improve flexibility, enhance balance, and promote overall wellness, and it suits all activity levels. Both activities are offered twice a month throughout the year at no cost for eligible county residents.

At Universal Dog Care Orlando, Tiny but Mighty Tuesdays highlights little dogs with outsized spirit. This daycare play day is tailored to smaller pups who enjoy safe play and friendly social time in a supervised setting designed just for them. Features include small-dog play groups that put safety first, socialization that boosts confidence, guided daycare activities, and plenty of enrichment with cute photo moments to remember it all. From bold and bouncy to cuddly and sassy, the spotlight stays on compact canines with big energy. Capes are optional, and confidence comes standard.

Connect with local entrepreneurs, business owners, and professionals at the bi-weekly meeting of the CLG Hunters Creek Chapter, a focused space to grow your business through genuine relationships and referrals. Expect an energetic, results-oriented atmosphere that goes beyond typical networking, turning meaningful conversations into real opportunities. The gathering is well suited for business owners and entrepreneurs, real estate and lending professionals, contractors and other service providers, marketers and creatives, as well as professionals aiming to expand their local reach.

Put your smarts to work at a trivia night hosted by Great Big Trivia. Enjoy friendly competition with prizes, no cost to participate, and an unlimited boneless wings and fries special for $19.99.

Old Town Kissimmee hosts a free, biker-friendly gathering that welcomes touring motorcycles of every kind, including Harleys, Indians, trikes, and slingshots. The event brings the rumble of engines back to the Old Town Entertainment District and focuses on the camaraderie of riders, a hallmark that has made it a favorite for the Central Florida motorcycle community. Participants must carry a valid driver’s license and proof of insurance. Colored patches are not allowed.

An afternoon card social at the Kissimmee Woman’s Club focuses on Hand, Foot and Toe, bringing together a welcoming group of women for play, friendly conversation and community. Both newcomers and seasoned players feel at ease, with guidance available for anyone learning or refreshing skills. The emphasis is as much on camaraderie as on the cards, and the mood stays light with plenty of laughter around the tables. Participants may bring their own lunch, and people arrive either solo or with friends.

Take the spotlight at Old Town during an inclusive karaoke night where anyone can sing. Confident crooners and off-key enthusiasts alike are encouraged to grab the mic, perform solo or with friends, and enjoy a few moments center stage. The performances take place on Old Town’s Main Stage next to Southern Breeze, creating a welcoming setup that puts you in the role of headliner.

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.

Classic horsepower takes center stage at this weekly Friday showcase and cruise. Eligible entries include show-ready muscle cars from 1964 or newer, along with hot rods and classics from 1985 or earlier. A cruise rounds out the evening, and all registered vehicles are welcome to roll out together. There is no charge for participating owners or for spectators. Classic car participants should use the Old Town entrance beneath the east (left) Jukebox signs, where event staff will greet drivers and arrange a security escort along the brick streets. Please avoid driving on the bricks unless permission is given. Old Town Cruisers can also take part in a monthly cash giveaway. Each Friday and Saturday cruise during the month earns an entry, and after the final Friday and Saturday cruises of the month, one winner is selected on each of those days to receive $1,000 courtesy of Old Town Kissimmee.

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.

Every Saturday, Old Town hosts a classic car tradition more than three decades in the making, featuring show quality hot rods, street rods, and antique vehicles from 1985 or earlier. The event is free for participants and free for spectators, offering an all ages outing for car enthusiasts and families. A cruise is part of the day, and all registered vehicles are welcome to take part. Participating drivers should enter Old Town beneath the east side Jukebox signs to meet event staff, who will arrange a security escort along the brick streets. Please do not drive on the bricks unless directed by staff. Old Town Cruisers can also take part in a monthly $2,000 giveaway, earning an entry each time they cruise on Friday and Saturday during the month. After the final Friday and Saturday cruises, one winner is drawn each day for $1,000 courtesy of Old Town Kissimmee.

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.