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Winter Garden is a city of about 50,000 people in west Orange County, Florida, roughly 14 miles west of downtown Orlando on the southern shore of Lake Apopka. Founded as a citrus and farming town in the early 1900s, it grew around the railroad that carried oranges and vegetables to northern markets.
Today its historic downtown along Plant Street is one of the most charming small-town centers in Central Florida, with brick storefronts, sidewalk cafes, the restored 1935 Garden Theatre, the Edgewater Hotel and two railroad museums. The West Orange Trail, built on the old rail line, runs straight through the middle of downtown, so cyclists and walkers drift in for coffee and ice cream all day.
On Saturdays the Winter Garden Farmers Market fills the downtown pavilion, and Plant Street Market offers local food stalls and a craft brewery. Nature lovers can explore Tucker Ranch and Newton Park on Lake Apopka, while Walt Disney World and the Orlando theme parks are only about 20 to 30 minutes south.
An indoor market hall in downtown Winter Garden with local food vendors, bakeries, coffee, a wine bar and Crooked Can Brewing Company at its heart. It is a casual place to graze, sit at long communal tables and drink a local beer. Weekend evenings are busy, so arrive early for a table.
A Mediterranean Revival movie palace on Plant Street that opened in 1935, closed for decades and reopened in 2008 after a community restoration. Inside, a starry ceiling and courtyard facades frame live plays, musicals, concerts and classic films. Check the schedule and book seats ahead for weekend shows.
A community art gallery on South Boyd Street, just off Plant Street, run by the local art association. It shows rotating exhibits by Central Florida artists, from painting and photography to ceramics, and hosts classes and receptions. Admission is free; pair it with a downtown walk and lunch nearby.
A long paved multi-use trail built on a former railroad line, running through the middle of downtown Winter Garden and out toward Oakland, Lake Apopka and Apopka. It is popular for cycling, running and skating. Bike rentals are available near downtown; ride early in the morning to avoid the midday heat.
An Orange County park on the south shore of Lake Apopka at the edge of Winter Garden, with a boat ramp, picnic shelters, a fishing area and wide views across one of the largest lakes in Florida. Sunsets over the water are lovely. It is a good place for a picnic after riding the nearby trail.
A small museum in a historic railroad depot on Plant Street that tells the story of Winter Garden's citrus groves, early settlers and railroad era through photos, tools and memorabilia. It is a quick, free stop that adds context to a downtown stroll. Volunteers are happy to answer questions.
A volunteer-run museum in an old depot building in downtown Winter Garden, packed with lanterns, signals, timetables, uniforms and model trains from the railroads that once served Central Florida's citrus towns. Admission is free and it is a hit with children. Hours are limited, so check before visiting.
A weekly Saturday morning market in the downtown pavilion with local produce, honey, baked goods, plants, flowers, crafts and food trucks. It is one of the busiest farmers markets in the Orlando area and has a friendly small-town feel. Come early for parking and the best selection, and bring cash for some stalls.
A large open-air shopping center on former citrus grove land near SR 429, with department stores, national chains, restaurants and a movie theater. It is the main place in west Orange County for practical shopping and dining. It can get busy on weekends; visit on weekday mornings for easy parking.
A large city-owned former cattle ranch on the shore of Lake Apopka that has been opened as a nature park, with oak hammocks, open pasture, walking trails and lake views. It is a quiet place for birdwatching and an easy walk away from the crowds. Bring water, bug spray and sun protection, as shade is limited.
A small historic hotel on Plant Street that opened in the 1920s and has been restored with period furnishings and a classic lobby. Even if you do not stay, it is worth a look as one of the landmarks of the downtown historic district. Rooms are few, so book well ahead for weekends and events.
A large golf complex near Winter Garden with two championship courses, a nine-hole course and one of the biggest practice ranges in the country, set among pines, wetlands and old citrus land. It is popular with visiting golfers staying near Disney. Book tee times ahead, especially in winter and spring.
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