Old Town Kissimmee with kids is an easy way to enjoy a lively evening without spending a day in a theme park. It is a small, walkable street of rides, shops, snacks and restaurants, and it is especially popular for its classic car shows. Here is how to plan a visit when you are staying at Windsor Hills Resort in Kissimmee.
What Old Town is like
Old Town is a nostalgic, outdoor entertainment district built around a brick-style main street. It feels more like a small-town fair than a theme park, which many families find a relaxing change after busy Disney days. Hours, ride availability and events change, so check Old Town's official website before you go.
Rides for kids
The area has classic fair-style rides, from gentle options for little ones to spinning and swinging rides for bigger kids. Each ride usually has its own height and age rules, so measure your kids and check the posted rules at the gate. It helps to set a simple budget in advance, since individual ride costs add up.
Car shows and weekend fun
Old Town is known for its classic car shows, with polished vintage cars lined up along the street. Dates and times can change by season, so check the current schedule. Kids who love cars will enjoy it, and parents will like that it is a low-key way to spend an evening.
Dinner and snacks
You will find a mix of sit-down restaurants and quick snacks nearby. If your group is hungry and tired, a casual meal works better than a long wait. For more options close to your rental, browse our guides to restaurants near Windsor Hills and kid-friendly restaurants near Windsor Hills.
Tips for visiting with kids
- Go in the late afternoon so you can see the lights come on.
- Bring comfortable shoes, sunscreen and bug spray.
- Agree on a ride budget before you arrive.
- Keep younger kids close in the evening crowds.
- Plan a calm morning the next day if you stay out late.
Where Old Town fits in your trip
Old Town is a great rest-day or non-park evening idea. Pair it with our list of things to do in Orlando that are not theme parks and hidden gems near Kissimmee. Windsor Hills is a gated resort about 10 minutes from Disney property, so it is a convenient base for both park days and evenings like this. There is no resort shuttle, so plan on a car or rideshare.
Plan your Old Town Kissimmee evening from Windsor Hills
After a night out, it is nice to come home to a rental with a full kitchen, private pool options and space for everyone to spread out. Booking direct with an owner keeps things simple. Browse Windsor Hills rentals and pick the home that fits your family.
