This weekend in Kissimmee, FL

● Listings verifiedMonday, September 21 · every listing checked against its source by our Kissimmee editors

Saturday & Sunday, Sep 26–27

3 events, 1 free. All of this week's events →

Saturday, September 26 2 events
  • 1pm

    Welcome Fall Festival: For the Girlies

    Marydia Community Center, 707 Sawdust Trl, Kissimmee · verified Sep 20
    See details

    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.

    Event website ↗
  • 1pm

    Saturday Classic Car Show & Cruise

    Old Town, 5770 W Irlo Bronson Memorial Hwy, Kissimmee · verified Sep 18
    Free

    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.

    Event website ↗
Sunday, September 27 1 event
  • 7am

    Superhero Race Against Cancer 5k

    Celebration Lakeside Park, 701 Front St, Kissimmee · verified Sep 20
    See details

    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.

    Event website ↗

Hosting something in Kissimmee? — Get your event listed in the directory and in the newsletter.

More events near Kissimmee

BaseLocal covers 900+ communities — these are next door.