Family events in Kissimmee, FL

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.

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.