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.


West Orange Trail - Oakland Nature Preserve Trailhead
140 Apopka Lake Rd, Oakland, FL 34760. (407) 654-1108 

For a breath of fresh air and a scenic outdoor adventure, lace up your walking shoes and head to the West Orange Trail, starting at the Oakland Nature Preserve Trailhead.

Our favorite part? The serene nature walk through lush landscapes, where you can spot local flora and fauna. Whether you choose to bike, jog, or simply take a leisurely stroll, the trail offers a peaceful escape into Florida's natural beauty.  

Oakland Nature Preserve 
747 Machete Trail, Oakland FL 34760. (407) 905-0054 

Enjoy hiking the upland trails or the Healthy West Orange Boardwalk to Lake Apopka, where you can see various birds and other wildlife. Visit the Jim Thomas Environmental Education Center and Museum to learn more about the area.

Check the calendar for scheduled events throughout the year. Whether you're a birdwatcher or simply seeking a tranquil setting for a leisurely stroll, the Oakland Nature Preserve provides an opportunity to connect with Florida's unique environmental treasures. Restrooms are available.

Central Florida Railroad Museum
101 S Boyd St, Winter Garden, FL 34787. (407) 656-0559 

Uncover the rich history of railroads at the Central Florida Railroad Museum in Winter Garden, just three miles from Oakland. Our favorite exhibit? The collection of vintage locomotives and railroad memorabilia that transports you to a bygone era of transportation.

Delve into the region's railway heritage and marvel at the well-preserved artifacts on display. Whether you're a history buff or simply curious about the locomotive legacy of Central Florida, this museum provides an engaging and educational experience for visitors of all ages. 

Tucker Ranch Recreation and Nature Complex
100 Avalon Road, Winter Garden, FL 34787.  (407) 656-4155 

Tucker Ranch is discussed earlier on this page and is three miles from Oakland. Dogs are allowed.


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