By  Mike Miller Updated December 28, 2021

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

Winter Garden, Florida is about 14 miles west of Orlando on State Road 50 in western Orange County, Florida. Winter Garden's population is slightly more than 45,000.

Historic Museum in Winter GardenHistoric Museum in Winter Garden

One of the first things a new Floridian has to do is learn the whereabouts of the "winter" towns:  

Welcome Arch in Winter GardenWelcome Arch in Winter Garden

Winter Garden, Winter Park, Winter Haven and Winter Springs.

I'll even mention Winter Beach over near Sebastian, but not many people remember it these days.


The first settlers came to the Winter Garden Florida area just before the Civil War in the 1850's. They established small farms along the south shore of Lake Apopka.

Winter Garden's economy depended largely on citrus and vegetable production. This economy was helped when the Orange Belt Railroad was completed and came through town.

By 1900, a small commercial district had popped up along Plant Street and residential neighborhoods began to appear on the side streets.

One of Many Fish Camps on Lake Apopka That No Longer ExistOne of Many Fish Camps on Lake Apopka That No Longer Exist

At one time, especially in the 1930's, Winter Garden's location on Lake Apopka made it a fisherman's paradise. Lake Apopka is one of the largest lakes in Florida.

Winter Garden Pool Vintage PostcardWinter Garden Pool Vintage Postcard

Some of the best bass fishing in the United States was to be had in the clean waters of Lake Apopka.  Winter Garden was the center of this fishing activity.

Huge agricultural operations along the northern shores of Lake Apopka resulted in toxic runoff into the lake and its glory days as a fishing paradise are lost in the distant past.


There are ongoing efforts to buy up the farms and improve the water quality of Lake Apopka.

There has been some success with this effort, and we should all keep our fingers crossed.

There are still many historic buildings in Winter Garden, most of them dating back to the period from 1915 to 1940.

Central Florida Railroad MuseumCentral Florida Railroad Museum

Many of the old railroad routes were combined into the West Orange Trail, a 22-mile long multi-use rail trail owned by Orange County.

Home in Winter Garden, FloridaHome in Winter Garden, Florida

The trail passes through downtown Oakland, Winter Garden, and Apopka. It is very popular with walkers, joggers and bicyclists.

Along the West Orange TrailAlong the West Orange Trail

Historic downtown Winter Garden contains an eclectic collection of restaurants,shops, cafes, a train depot that is now a museum, and a theater.

Downtown Winter GardenDowntown Winter Garden

Brick paving, tree planters and benches make this a favorite spot for locals and tourists to visit.

A few blocks north of downtown Plant Street are several public parks, a public swimming pool and community center.

Winter Garden Florida Trailer CityTrailer City, Winter Garden

This area also has a large city owned trailer park called Trailer City that opened in 1936 and is home to a couple of hundred happy people.


There are many things to do in Winter Garden that are fun and don't cost a lot of money, especially if you stay in the downtown area.

You will be close to many fun things to do.  There are movie theaters, many shops and restaurants, and frequent cultural events. 


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