Instructions:
1....Print this file.
2....At its end, click on "rules" to see a copy of the trail rules, print it, and then click where indicated at the end of the 3-page rules and patch order form to get back to the list of Florida trails.
3....If you want a hand-drawn map showing the locations of all of the sites, send a self-addressed stamped envelope to Steve Rajtar, 1614 Bimini Dr., Orlando, FL 32806.
4....Hike the trail and order whatever patches you like (optional).
WARNING - This trail may pass through one or more neighborhoods which, although full of history, may now be unsafe for individuals on foot, or which may make you feel unsafe there. Hikers have been approached by individuals who have asked for handouts or who have inquired (not always in a friendly manner) why the hikers are in their neighborhood. Drugs and other inappropriate items have been found by hikers in some neighborhoods. It is suggested that you drive the hike routes first to see if you will feel comfortable walking them and, if you don't think it's a good place for you walk, you might want to consider (1) traveling with a large group, (2) doing the route on bicycles, or (3) choosing another hike route. The degree of comfort will vary with the individual and with the time and season of the hike, so you need to make the determination using your best judgment. If you hike the trail, you accept all risks involved.
One of the first settlers of this portion of the county was W.C. Roper, who arrived in 1857 from Merriwether County, Georgia. While on a homesite prospecting trip on horseback, be bought 600 acres along the shore of Lake Apopka, between present Winter Garden and Oakland. He returned in 1858 with his family.
Roper had ten children and his family group, including slaves, numbered 28. In January of 1860, the B.B. Reams and A.J. Dunaway families, also from the same part of Georgia, settled here. Roper farmed and operated a sawmill, grist mill, sugar mill, and a cotton gin, and later had a tannery for making shoes. He served as Orange County's Superintendent of Schools from 1873 to 1877.
This is the oldest remaining church in Orange County, having been built between 1860 and 1865. The building was substantially remodeled in 1945. In the 1970s, it was known as the Zion Baptist Church.
The community of Beulah was originally known as the Reaves Settlement. In January of 1860, B.B. Reams and his family arrived here from Georgia. They were followed by the Reaves family in 1867, and the O'Berry family in the 1890s.
There were many members of the Reaves family living in and near Beulah, as evidenced by the high percentage of headstones bearing that name. They also gave their name to Lake Reaves, reached by following Reaves Rd. southward.
This school opened in 1976, replacing Lakeview High School.
Another settler of Winter Garden was Kit Johns, who arrived just after the Civil War. He lived in a small log house on what is now E. Story Rd.
This building started as a black-owned movie theater, popular in the 1940s and 1950s. Eatonville Diversified, Inc. renovated it in 1979 to provide a community gathering place.
Macedonia Lodge No. 49 A.F.A.M. was founded in 1907. Its home here was dedicated on November 28, 1971. The building is also the home of other fraternal groups.
This church was organized in 1912 by Eld. John McCall. This sanctuary was built in 1974 under the supervision of Eld. A.W. Whitehead.
This church building was erected in 1951, under the supervision of Rev. J.W. Calloway, pastor.
This congregation organized in Ocoee on August 26, 1888, with nine members. Those instrumental in its founding were Rev. J.A. Richardson, J.L. Dillard, A.W. Hurley and W.L. Story. The church moved to a wooden building across the street at 114 E. Plant St. (where the Rainbow Supermarket now sits) in 1915 when J.S. Dillard offered them $250 to move to Winter Garden.
This formerly was the site of a large sawmill operated by Will Pennington. In 1922, while J.B. Holley was the pastor, the present brick sanctuary was built, with an auditorium that seats 600. The architect was J.J. Baldwin, and R.W. Wimbish was the builder.
This church has been active in starting other churches as missions - the First Baptist Church of Windermere, the Park Ave. Baptist Church, the Oaklevel Baptist Church, and the Starke Lake Baptist Church. It also started a ministry at the Oakland/Winter Garden Campground in 1977.
In the 1880s, this was the location of the railway depot of the Orange Belt Railroad, which Peter Demens extended to St. Petersburg. The Atlantic Coast line replaced it around the turn of the century with another wooden depot, and later with the existing brick building on the northeast corner (1 N. Main St.). For a while, that building housed the Winter Garden Chamber of Commerce.
This bank began in 1908 with Dan McKinnon as its president.
A.B. Newton arrived here from Mississippi in 1892 and opened a dry goods and notions store at this location. He applied for a post office, but was turned down as a result of protests from the Oakland and Ocoee post offices. His application was later approved, and his post office opened on December 28, 1892.
Newton's store was the first in Winter Garden, at a time when the settlement consisted of about six houses, a sawmill, and a railroad depot. He also was the city's first mayor when it was incorporated in 1908, published the city's first newspaper (the Ricochet), and was the station agent for the Orange Belt Railroad.
To the west of Newton's store was located Geo. T. Smith & Co. That is now the site of the Block Building, at 12 W. Plant St.
The present buidling on the Newton site was erected in 1912.
This depot was built in 1913 to serve the Tavares and Gulf Railroad. T & G's tracks intersected with the Atlantic Coast Line's to the west of this site. Although T & G was purchased by the Seaboard Air Line in 1926, it continued to operate as a separate company until it was absorbed into the Atlantic Coast Line System in 1969. Shortly thereafter, the track from Winter Garden to Tavares was abandoned and the track was connected to the line at Ocoee to provide service to this city.
The building was purchased in 1979 by the Central Florida Chapter of the National Railway Historical Society, and after renovation the present museum opened on May 21, 1983.
On November 22, 1986, the Florida Central Railroad took over operation of the 55 mile branch line serving Winter Garden.
The museum is open to the public. There is no admission charge, but donations are gladly accepted.
This was Winter Garden's second bank, beginning in 1917. Neither First National nor the State Bank of Winter Garden survive today.
This three-story brick hotel was completed in 1927. It had a telegraph office, electrical heating and a fire sprinkler system, and was the only hotel in west Orange County for nearly three decades.
In 1925, the unfinished building had an uncertain future until citrusman Jerry Chicone Sr. arranged for local investors to complete it. It opened with 52 rooms two years later and served as a central gathering place for the town.
It ceased being a hotel in the late 1950s, the upper floors were closed in the 1960s, and an attempt at turning the building into an apartment house was begun in the early 1970s. The building was condemned in 1972 and boarded up. Many plans were discussed for renovating or teating down the building, but it remained unoccupied for several years.
Finally, on November 7, 2003, it reopened as a 22-room bed and breakfast.
This church was organized on March 24, 1895, as the Beulah Methodist Church. When its first building was erected in 1897, it was called the Beulah Methodist Episcopal Church South.
The congregation moved to Winter Garden in 1909, meeting under a brush arbor one block east of here. A sanctuary was built at that location, and new property was acquired here in 1925.
The present brick sanctuary, known as the A. Livingston Mission Church, was built in 1939-42. The adjacent educational building was erected in 1946-51.
From 1870 to 1880, Lafayette Mills carried the mail around Lake Apopka for free. In July of 1953, this building opened on the site of the former Winter Garden Citrus Growers Association building, which burned down here in the 1920s. The present post office was remodeled in 1963.
This theatre was built by Collie Biggers in 1935 with a Mediterranean style. Biggers, a former Sanford motorcycle policeman, moved to Winter Garden in the early 1920s with the goal of bringing moving pictures to the public. After showing silent movies at the Movie Hut on E. Plant St., he then built the Winter Garden Theatre at 158 W. Plant St. After it burned down in 1934, he built this one with an air conditioning system - fans blowing over big chunks of ice. It claimed to be the first Central Florida theatre built for sound movies.
The theatre closed in 1963 after years of low attendance. For many years before a restoration project began in 2004, the building was used for storage of lawnmower parts and other equipment for the next-door Pounds Motor Co. It was restored to be a 344-seat community theatre for musical, dance and comedy performances, performing arts classes and student recitals, and movies.
The previous city hall, built in 1937, was torn down in 1979 to make room for this modern building. The municipal complex was built by L.B. Samford, Inc. of Miami.
When J.S. Dillard arrived in 1888, he cultivated land which he called the "Washington Place". Later, it and the town became known as Winter Garden.
This log cabin style building with a stamped tin roof is the headquarters of Post No. 63 of the American Legion, and the popular home of bingo. The monument in front, honoring the veterans of all wars, was dedicated on Veterans Day, 1960.
The Winter Garden Masonic Lodge #165 F.&A.M. was chartered on January 16, 1907, as South Apopka Lodge #165. Its home here was built in 1951-52.
The land for this school was donated in 1927 by Luther Fuller Tilden, a developer of citrus groves and vegetable fields. Construction of the school was supervised by his son, Will Tilden. Additions included a gymnasium in 1951 and a cafeteria in 1960. The student body became integrated in 1965. In 1976, with the opening of West Orange High School, it was converted into a middle school.
The school was designed by M. Leo Elliott, Inc., and was constructed by Daugherty-Nichols-Young, builders.
This is near the end of Phase I of the West Orange Trail, beginning about 3.2 miles to the southwest in Killarney. It is part of the national Rails to Trails movement, converting to recreational use land which once was under railroad ties and rails. It is planned to eventually extend to Apopka.
This park is dedicated to Winter Garden's citizens who died while serving in World War I, World War II, Korea and Vietnam.
Early Settlers of Orange County, Florida, by C.E. Howard (1915)
Flashbacks: The Story of Central Florida's Past, by Jim Robison and Mark Andrews (The Orlando Sentinel 1995)
The History of Public Education in Orange County, Florida, by Diane Taylor (Orange County Retired Educators Association 1990)
The History of Winter Garden, Florida, by Bea Deariso (1958)
Oakland: The Early Years, by Eve Bacon (The Mickler House 1974)
Orlando: The City Beautiful, by Jerrell H. Shofner (Continental Heritge Press 1984)