Best Things to Do near me in Winter Garden, FL

Planning a day in downtown Winter Garden

Plant Street is the center of everything. The West Orange Trail runs right through downtown, so you can rent a bike near the Winter Garden station, ride a stretch toward Oakland or Killarney, and be back for lunch. On Saturdays, start at the farmers market pavilion, where live music plays through the morning and leashed dogs are welcome.

The Winter Garden Heritage Museum and the Central Florida Railroad Museum are both free and both downtown, so they fit easily between other stops. They are small, which makes them ideal for kids with short attention spans or for a rainy afternoon.

Tips for visiting Winter Garden

Go early on summer weekends. The trail has little shade in places, and the market is most comfortable in the morning. Trail stations have parking and restrooms, and downtown street parking fills up on Saturdays, so arrive before the market gets busy. Plant Street's cafes and restaurants make it easy to turn a morning outing into a full day.

About this list

Every place here is a locally run business in Orange County with its own website, which we checked for hours, menus and contact details. We leave national chains off our best-of lists and favor places with a clear specialty.

This page covers 7 things to do in Winter Garden. You'll find them in Downtown Winter Garden, Hamlin and Horizon West.

About Winter Garden

Winter Garden in west Orange County is built around its historic downtown on Plant Street and the West Orange Trail. Fast growth in Horizon West has brought many new home service companies, clinics and restaurants to the area.