West Orange Trail

The Winter Garden Downtown Historic District is a U.S. historic district in Winter Garden, Florida. It is bounded by Woodland, Tremaine, Henderson, and Lakeview Streets, encompasses approximately 100 acres (0.40 km2), and contains 26 historic buildings. Among the 26 buildings are the Winter Garden Heritage Museum, Garden Theatre, Tony's Liquors, the Dillard & Boyd Building, and many more. The oldest confirmed of these are the Dillard & Boyd Building and 36 W. Plant Street, both dating to 1912 (there are some buildings which may be older, however sources cannot confirm their date of construction). On August 1, 1996, it was added to the U.S. National Register of Historic Places.

The Garden Theatre is a refurbished, historic theatre located at 160 West Plant Street in Winter Garden, Florida. The Garden Theatre, which hosts over 200 events a season, including professional level theatre, music, dance, and films. The Garden Theatre serves as the primary performing arts center for the Winter Garden area.

The Withers-Maguire House is a small event venue and historic house museum in Ocoee, Florida. It is located at 16 East Oakland Avenue and is owned by the City of Ocoee. It was added to the U.S. National Register of Historic Places on April 2, 1987. The builder was retired General William Temple Withers, a native Kentuckian, who began wintering in Florida in 1884. He spent much of his time acquiring land in western Orange County and growing citrus. In 1888, he built this house and lived here until his death the following year. Withers’ widow, Martha, sold the house and its furnishings in 1910 to David O. Maguire and his family, whose house had recently burned. Like Withers, Maguire was very involved in citrus growing, and the family became prominent citizens in Ocoee. Maguire's son, Fred, was Ocoee's first mayor, and another son, Raymer, was the first city attorney. David Maguire died in 1913, but members of his family continued to reside in the house until 1979. After a commercial venture to convert the home to offices was abandoned, the City of Ocoee acquired the house in 1984. It was listed on the National Register of Historic Places in 1987. Made from pine cut and milled on this site, it is an example of Stick Victorian style architecture. One of the finest houses in west Orange County, it was one of the first to have concealed electrical wiring and closets. The city restored the house following its acquisition using a combination of city funds and a State of Florida grant. The downstairs rooms is available for rental and is suitable for smaller gatherings or to support an outside event. A modern catering kitchen is available. The upstairs rooms serve as a museum depicting early 1900s life in Ocoee. Current information regarding the City of Ocoee can be found here.

The Ocoee Christian Church is a historic Carpenter Gothic church in Ocoee, Florida. It is located at 15 South Bluford Avenue. On March 28, 1997, it was added to the U.S. National Register of Historic Places. The church is affiliated with the Christian Church (Disciples of Christ) and is believed to be the oldest church of that denomination in continuous use in Florida.

The Winter Garden Historic Residential District is a U.S. historic district in Winter Garden, Florida. It is bounded by Plant, Boyd, Tilden, and Central Streets, encompasses approximately 250 acres (1.0 km2), and contains 76 historic buildings. On August 1, 1996, it was added to the U.S. National Register of Historic Places.

Winter Garden is a city in western Orange County, Florida, United States. Located 14 miles (23 km) west of Downtown Orlando, it is part of the Orlando metropolitan area. The population was 46,964 as of the 2020 census.

Woman's Club of Ocoee is a national historic site located at 10 North Lakewood Avenue, Ocoee, Florida in Orange County.It was added to the National Register of Historic Places in 2011.

WXXL (106.7 FM) is a commercial radio station licensed to Tavares, Florida, and serving the Greater Orlando - Central Florida radio market. The station airs a top 40 (CHR) radio format and is owned by iHeartMedia. The studios and offices on Maitland Center Drive in Maitland. WXXL has an effective radiated power (ERP) of 100,000 watts. The transmitter is on Story Road at Veterans Memorial Park in Winter Garden.

Ocoee () is a city in Orange County, Florida, United States. According to the 2019 US Census population estimate, the city had a population of 48,263. It is part of the Orlando–Kissimmee–Sanford, Florida Metropolitan Statistical Area.

West Orange High School is a high school located in Winter Garden in southwest Orange County, Florida, United States. West Orange serves Winter Garden, Oakland, Tildenville, and parts of Lake Butler and Ocoee.

Minorville is at the intersection of SR 50 (Colonial Drive) with former SR 439 (Bluford Avenue) and CR 526 (Old Winter Garden Road). It is inside the city of Ocoee, Florida

Lake Bennet, also spelled Bennett and also known as Lake Blanchard, is a somewhat kidney-shaped natural freshwater lake in Orange County, Florida. Florida State Road 50 (West Colonial Drive) travels over the south end of this lake. On the lake's northeast is the Lake Bennett Health & Rehabilitation Center. This lake is surrounded by commercial properties. The lake has a fountain on the south end. There are no public boat ramps or swimming areas on this lake. The Hook and Bullet website says this lake contains largemouth bass, bream, bluegill and crappie.