The city has a total area of 12.1 square miles and is bordered on the south by the town of Windermere and on the east by the city of Ocoee. The toll road Western Beltway (SR 429) was completed in late 2006 and it links I-4 near mile marker 58 in Osceola County with Florida's Turnpike at Winter Garden. Other major roads through Winter Garden include Orange County Road 535 and Orange County Road 545. CR 535 (also called Winter Garden - Vineland Road) begins at SR 50 and bisects the southern half of the city and proceeds south to Windermere, Lake Buena Vista and Walt Disney World where it becomes State Road 535.

The West Orange Trail:
The West Orange Trail is a 14 foot wide, 22 mile long paved bicycle trail following an abandoned railroad line that ran through the heart of historic downtown. The trail passes through downtown Oakland, Winter Garden, and Apopka. Today, more than 50,000 cyclists, skaters and walkers use the trail every month. Horseback riders will also be able to enjoy a parallel equestrian path, five-feet wide and ten-miles long, extending north and south of Clarcona Horse Park. Florida law requires all bicyclists under age 16 to wear a bicycle helmet.

The Garden Theater:
Originally built in 1935 as a single screen cinema, the Garden Theater was the first theater in Central Florida built for “talkies” (the first movies with sound), and was a gathering place for locals to watch the latest newsreels and films of the day.

Constructed in the Mediterranean Revival style, the interior of the theater was modeled after a Spanish courtyard with “Romeo & Juliet” balconies, Spanish tile roof and a dark blue ceiling resplendent with stars.

The theater closed in 1963, and soon after became a tractor warehouse and showroom for the Pounds Motor Company located next door. The theater was restored through the efforts of the Winter Garden Heritage Foundation, and the Garden Theater reopened in February 2008 and now hosts over 200 events per season. The Garden Theater hosts live plays, concerts, special events, movies, and vintage, cult, and micro-budget flicks.

The Central Florida Railroad Museum:
The Train Museum located at 101 S. Boyd Street is dedicated to preserving railroad history, especially that of the Central Florida area. They have an extensive collection of railroad memorabilia, housed in the old Tavares and Gulf railroad depot built in 1913 and located in the historic section of Winter Garden. You are invited to attend monthly Chapter meetings the second Monday of each month at 7:00 PM at the Train Museum. The Florida Central Railroad serves Winter Garden with the tracks to the museum being the end of the line for the Winter Garden branch. Memorabilia on display includes historic photographs, lanterns, telephones, telegraphs, stoves, tools, furniture, timetables, tin ware, marker lanterns, ticket punches, lamps, uniforms, locomotive bells and whistles, a 1938 Fairmont motorcar, a velocipede hand car and a very large collection of dining car china and silver service. Outside there is a former Clinchfield caboose #1073 and a three head interlocking signal from the former ACL SAL junction in Plant City. Open 350 days a year from 1 p.m. to 5 p.m.

The museum is solely supported by donation and fund raising events of the Central Florida Chapter. The Central Florida Chapter is a non-profit educational Florida corporation and has been granted 501 (c) 3 status by the IRS; therefore all donations received are tax deductible.

The Edgewater Hotel:
The Edgewater Hotel was opened in 1927. Construction of the Edgewater hotel began in 1923. With the placement of the final brick on top of the east wing facade on June 1st, 1926. The Edgewater opened January 26th, 1927. From the antique sinks and fixtures to the original, manually operated Otis elevator, the Edgewater is a bed and breakfast experience like no other in the Orlando area. The ground floor features Thai Blossom serving lunch and dinner, The Tasting Room serving lunch and dinner, and The Chef's Table fine dining serving dinner, also Scoops Old Fashioned Ice Cream Store. In the early to mid 1940's the Army utilized the hotel during World War II to house soldiers on their way overseas. The impact of the soldiers' stay at the Edgewater can still be evidenced by the telltale wear marks on the hotel lobby floor. The Edgewater sheltered everyone from businessmen to fishermen, including the Washington Senators during spring training, and famous Hollywood celebrities like Clark Gable.

The Winter Garden Farmers Market:
The Farmers Market is every Saturday 9am to 2pm year-round at the South Boyd Street lot. Listen to live music, browse the large selection of vendors from locally grown produce and baked goods, to homemade soaps and fresh flowers, and you can even bring your four-legged friends.

The Heritage Foundation hosts over 35,000 local, national and international visitors annually and operates the only two museums in our area: the Winter Garden Heritage Museum and the Central Florida Railroad Museum. Both are free and open to the public 350 days a year from 1 p.m. to 5 p.m.

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