By  Mike Miller Updated November 27, 2023

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. 

Plant Street MarketPlant Street Market

PLANT STREET MARKET is a locally owned venue in one of downtown Winter Garden's historic buildings that focuses on natural foods, organic food, and handmade craft objects from the local community.

The market and other attractions are all located along or near West Plant Street, the main street through downtown with its centerpiece being the West Orange Trail.

Crooked Can Brewing CompanyCrooked Can Brewing Company

CROOKED CAN BREWING COMPANY is located in Plant Street Market and produces and serves hand crafted beer.  It's a great place to catch some live music while you do your shopping.

Bridge on West Orange TrailBridge on West Orange Trail

WEST ORANGE TRAIL is a multi-use path that has been built on the former route of the old Orange Belt Railroad.   It is one of the most popular bike trails in Central Florida.

The trail is 22 miles long and begins west of Winter Garden and extends all the way north to Apopka along the south and east sides of Lake Apopka.  There are four main stations along the route with parking lots and restrooms.

One of my favorite things to see on the trail is the butterfly garden.  All features related to the trail have free admission.

Central Florida Railroad MuseumCentral Florida Railroad Museum

CENTRAL FLORIDA RAILROAD MUSEUM is located in the former Tavares and Gulf railroad depot built in 1913.  It contains exhibits showing Central Florida's railroad history.  A interesting collection is of dining car china.  

The building is located in the downtown area included in the National Registry of Historic Places.

WINTER GARDEN HERITAGE MUSEUM was founded in 1998 and is located in historic downtown Winter Garden.  It displays artifacts from the city's past.  It is located within the former Atlantic Coast Railroad Depot that was built in 1918.

Edgewater HotelEdgewater Hotel

THE HISTORIC EDGEWATER HOTEL opened in 1927 and is in the heart of downtown Winter Garden.  It has been totally restored and the second and third floors have beautifully furnished rooms that are managed in bed and breakfast style.

The ground floor of the building features some popular restaurants including the Chef's Table for fine dining and great food, The Tasting Room, and Thai Blossom.

Winter Garden Farmers MarketWinter Garden Farmers Market

WINTER GARDEN FARMERS MARKET is held every Saturday morning in historic downtown.  Local farmers and vendors display fresh produce and other good from 8am to 1pm.


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