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.
In 1913, Ransom Eli Olds bought 37,541 acres on the northern tip of Tampa Bay from Richard Peters for $400,000. He had invented the Oldsmobile and REO automobiles, and turned to land development. The first name of the town was R.E. Olds-On-The-Bay, but was changed to Oldsmar.
The early settlers had to go to Tarpon Springs or Dunedin to visit a store. Water was obtained from individual wells and collected rain. Despite the primitive conditions, Oldsmar was on the route from Tampa to St. Petersburg before the causeways were built.
Olds brought in surveyors and engineers from Boston to create a town modeled after the tree-lined boulevards of Washington, DC. Streets paved with oyster shells were named by Olds. He advertised heavily in the Detroit newspapers, using the slogan "Oldsmar for Health, Wealth and Happiness".
Olds encouraged his Detroit workers to move to Oldsmar. The housing he provided for his employees often was substandard, lacking proper sanitary facilties.
In the early 1920s, Olds disposed of his holdings in Oldsmar at a loss of $3 million. He had planned Oldsmar to be a city of 100,000. When he left, the population was about 200.
After Olds left, lots were still for sale by Harry A. Prettyman, a promoter from St. Louis. He was caught in 1927 selling underwater lots. In an attempt to avoid scandal, the town's name was changed to Tampa Shores. It was changed back to Oldsmar in 1937, two years after the last R.E. Olds land was sold.
This park dedicated to Olds includes a baseball field dedicated in 1964 to Charlie Fadeley, who in 1960 founded the Oldsmar Little Major League.
This house was built in about 1918 on Congress St., and was later moved here.
A Casino, later renamed the Two Bits Club, was built on the shore of the bay, serving busloads of people from Tampa and Pinellas County. A thousand foot pier stretched into the water, and was used to smuggle rum from the islands during Prohibition.
Olds drilled for oil in 1921 on the grounds of the present racetrack, originally named Sunshine Park, but hit water instead of oil. It has been said that oil was poured into it daily to make it look like Olds had reached an oil deposit. The well has now been capped.
In 1923, Olds realized that the town was not growing as he had planned, and started trying to get back some of the $4.5 million dollars he had invested in it. He traded this racetrack, nearly completed, for the Fort Harrison Hotel in Clearwater. He traded the rest of the land for the Belerive Hotel in Kansas.
The racetrack, which opened for its first season in February of 1916, was a financial success and helped Oldsmar through the lean years, despite being outside the city limits. Thousands of visitors drove in for the racing season, and horse owners often stayed in Oldsmar for the winter.
Before the days of the long bridges, Oldsmar was on the driving route from Tampa to St. Petersburg, and quite a bit of traffic came through here. After the Gandy Bridge was built in 1924 and the Courtney Campbell Parkway opened in 1934, traffic through this town was greatly reduced.
In 1921, Oldsmar's first hotel was built, and catered to tourists. On the first floor was a drug store, grocery store and hardware store. The hotel burned down in 1946.
This building with Italian polished tiles on the east and north walls was erected in 1918-19 and was the home of the Oldsmar State Bank into the 1920s. It was also the headquarters of R.E. Olds Farm Company and Oldsmar Land Development Company. During the 1950s, it housed a delicatessen and the post office on the first floor. Upstairs was a teen hangout for dances and other activities.
Oldsmar's first library was established in 1919 by the Woman's Club, under the leadership of Mabel Robbins. It was donated to the city in 1977 and moved into the City Hall Annex at 105 State St. It moved out in 1982, but returned here on July 11, 1991, after a $670,000 renovation and remodeling. During the years that the library was gone, this building was used as city government offices.
In the 1950s, this building was constructed to be the fire station. It also housed the police department, which was abolished in 1975 and replaced by the Pinellas County Sheriff.
From June 17, 1982, until 1991, this was the home of the library and the Parks and Recreation Department. In 1995, this was renovated to be a Community Center for the Parks and Recreation Department.
This small building was constructed before 1916 for workers hired to build the town. After they were no longer needed, this house was donated to the Woman's Club. In it, they founded and operated the library from 1919 until 1977.
This home was built in about 1924 by Louis London, brother of famous author Jack London. Louis received an Alaskan totem pole from his brother, which stood for years in this front yard. It was later donated to Oldsmar Elementary School and erected on its roof.
Jim H. Thompson was a shareholder in R.E. Olds Farm Company, formed to develop this town. This house was built in 1918, and the Thompsons lived here from then until 1922. Thompson also served as the president of Oldsmar State Bank.
The town's school was held in the black church and then in a private home built here in about 1918, and moved out when the schoolhouse was built in 1921. The house also served as the parsonage for Rev. Dr. L.H. Shumate.
This two-story bungalow is one of the original six homes built here between 1918 and the early 1920s. All were built as two stories, but this one caught fire and was restored with one. It was owned by R.E. Olds Farm Company as a rental or guest home for prospective buyers.
A wood frame school was built here in 1921 at a cost of $10,000. One room served the students in grades 1-4, another was for grades 6-8, and the high school was in the hall. In 1928, the school closed because of a lack of students. It reopened in 1943, and was torn down in December of 1981.
This school was constructed in 1959 with a single classroom, and has been expanded several times since then. Older students attend Safety Harbor Middle School and Clearwater High School.
With three stories, this is the largest of the original Oldsmar homes still standing. It was built for Edward Mitchell in 1917. Arlington Ave. was originally named St. Louis Ave., after the home town of promoter Harry A. Prettyman, but was renamed after his involvement in the 1927 scandal. Early promotional postcards of Oldsmar show a picture of this home with a St. Louis Ave. address.
This two-story Spanish style house has a covered entrance portico and a one-story addition, making it the largest of the many homes of this style built in Oldsmar during the 1920s. Recent owners include Claude and Francoise Jean.
The Methodist Episcopal Community Church was founded under the leadership of Rev. G.E. Bennett from Tarpon Springs. They held their first services in an unfinished bungalow across the street. They then moved to the Assembly Hall above the bank (now the second floor of the library), but abandoned that plan soon after when the back stairs turned out to be difficult for some of the members. They then moved back to the bungalow.
The first church building with Spanish style architecture was dedicated on March 8, 1925. It was torn down in 1956, and the present sanctuary known as Manahan Hall was completed in 1957. Inside, the original pews are still in use.
Oldsmar Past & Present, by Howard Brown (Linda's Print Inc. 1982)
Reflections of Oldsmar, by Paula Geist (Oldsmar Library 1996)
Yesterday's Florida, by Nixon Smiley (E.A. Seeman Publishing, Inc. 1974)
Click here for a copy of the trail rules.