By  Mike Miller  Updated November 27, 2023

Oakland, Florida Things To Do, Lodging, Dining, & Real Estate At End Of Article

Oakland, Florida is a small town of about 3,500 people located just west of Winter Garden.  

It is on the southern shore of Lake Apopka and a stop on the West Orange Trail, a popular "rails to trail" bike and pedestrian path in this part of Central Florida.

Classic Home on Old State Road 50, OaklandClassic Home on Old State Road 50, Oakland


Oakland began to boom when the Orange Belt Railroad came through town in the 1880s to serve the booming citrus industry. 

It was a narrow gauge railway that ran from Sanford to St. Petersburg. The biggest shareholder in that railroad was Peter Demens. 

He ended up running the railroad to St. Petersburg, naming the city after his hometown in Russia.

Oakland's economic fortunes began to decline when the railroads pulled out of town more than 100 years ago. 

The great freezes of 1894 and 1895 killed most of the citrus groves, and the railroads had nothing more to ship. 

Then along came a fire in the late 1890's that destroyed most of the downtown. 


The route of the original railroad is now the West Orange Trail, a favorite of walkers and cyclists from everywhere.

Oakland Town HallOakland Town Hall

Most people who live in this town don't want to go back to the booming old days in Oakland.

Home in Oakland, FloridaHome in Oakland, Florida

It is primarily a residential community, and the residents prefer the quiet serenity that now prevails. 

There are some interesting things to do in and near Oakland:

Oakland Nature PreserveOakland Nature Preserve

Oakland Nature Preserve has 128 acres that are examples of several ecosystems typical of Florida.  The preserve is open every day and has more than 13 miles of trails and boardwalks, along with an education center.  Admission is free.

Tucker RanchTucker Ranch

Tucker Ranch is a large park owned and managed by the City of Winter Garden.  It has 209 acres just off Avalon Road along the shoreline of Johns Lake.  The park has a children's play area, canoe and kayak launching area, and waterways to explore.

West Orange Trail MapWest Orange Trail Map

West Orange Trail is a rail to bike trail that is more than 22 miles long and goes through Oakland.  The trail extends from Killarney just west of Oakland through Winter Garden to the east and all the way to Apopka.

Historic Downtown Winter GardenHistoric Downtown Winter Garden

Winter Garden is only 3 miles east of Oakland and has a vibrant downtown area with abundant shops, hotels, restaurants, museums, parks, and plenty of places to just sit and enjoy people watching.

You will enjoy a visit to the quiet little Old Florida town of Oakland.


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