By James | Last updated August 23, 2023
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Located around 14 miles west of downtown Orlando on the shores of Lake Apopka, the approach to Winter Garden along State Road 535 is not very inspiring but as soon as you hit Plant Street, everything changes.
The Winter Garden Downtown Historic District straddles Plant Street and Main Street with the imposing brick-built First Baptist Church at the eastern end and the City Hall at the other. The Deco inspired City Hall was built in 2008 whilst the First Baptist Church dates back to the 1880s.
Lining the two streets are a collection of pretty independently run shops, boutiques, cafes, restaurants, a theatre, a couple of museums and a splash park.
At Ms. Bees Candy and Popcorn store they have a vast range of candies (sweets) plus over 50 different flavours of popcorn. A few doors away a French patisserie sells freshly baked bread, croissants and fantastic tarts and other pastries.
Throughout the year there are a number of local events in Winter Garden and every Saturday morning there is a weekly Farmer’s market and on the third Saturday of every month there is a Cruz-n-Car Show in the early evening. Centennial Plaza plays host to a free concert each Friday evening.
Open spaces in Winter Garden include Newton Park on the Lake Apopka shore and the new Tucker Ranch Nature Preserve and Recreation Area which will be opening in March 7, 2015 offering canoes and kayaking, playground, picnic pavilion and nature trails.
To the south of Winter Garden on Daniels Road is the Winter Garden Village, a 1,100,000 square feet (100,000 m2) open air shopping centre with a large range of retail chain stores and restaurants.
The Winter Garden Heritage Foundation was set up in 1991 to preserve Winter Gardens’s heritage and architecture and today it runs the two museums, the Central Florida Railroad Museum and the Winter Garden Heritage Museum as well as the Garden Theatre.
Central Florida Railroad Museum
The Central Florida Railroad Museum is located just one block south of the downtown district in the former 1913 depot of the Tavares and Gulf Railroad.
It houses a large collection of dining car china and silverware as well as a couple of vehicles, a goods wagon (caboose) and model railroad layouts. A second caboose is located outside the nearby Heritage Museum.
Admission is free and the museum is open every afternoon except major holidays from 1 p.m. to 5 p.m.
Winter Garden Heritage Museum
Like the Central Florida Railroad Museum, the Winter Garden Heritage Museum is also housed in an old railroad depot building, in this instance, the 1918 Atlantic Coast Line on Plant Street.
The museum helps preserve the local history, culture and heritage of the Winter Garden area through a large number of different exhibits, including Timucua Indian artefacts, old photos, local war heroes and the citrus and sports fishing industries.
You cannot miss the building with its large yellow railroad caboose wagon and vintage fire truck outside.
Admission is free and the museum is open every afternoon from 1 p.m. to 5 p.m.
The Garden Theatre located at the western end of Plant Street opened in 1935 as a cinema (movie theatre) complete with Romeo and Juliet balconies.
It closed in 1962 and the building was acquired by the Foundation in 2004. It has been fully restored as a performing arts centre and cinema hosting concerts, plays and movies.
West Orange Trail
Plant Street is part of the 22 mile long West Orange Trail that runs from Killarney Station on State Route 50 (mile marker 0), eastwards through Oakland, Chapin, Winter Garden and Clarcona before finishing just beyond Apopka to the Northeast at Welch Road. There are plans to further extend the trail northwards and when eventually completed the trail will be 36 miles long. The West Orange Trail in turn forms part of the planned Central Florida Loop.
There are several bike shops in Winter Garden where you can hire a bike to explore part of the trail. For the most part, the trail follows former railroad tracks.
Winter Garden History
Winter Garden was originally home to the Timucua Native American Indians but the fertile soil and good climate encouraged European settlers in the middle of the 19th century, especially after the end of the American Civil War.
The introduction of two railroad in the late 1800s saw an increase in occupation and the area become well known for the growing of citrus crops, adopting the name Winter Garden because of the year round growing opportunities.
There were eight citrus packing plants inside the city limits in its heyday but several devastating freezes during the 1980s saw the death of large swathes of orange groves.
Nearby Lake Apopka also became a magnet for bass fishermen and the Edgewater Hotel opening in 1927.
Today Winter Garden uses the slogan “a charming little city with a juicy past” and the Winter Garden Downtown Historic District is on the National Register of Historic Places.