Destination Main Streets

Winter Garden, Florida

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Winter Garden, Florida's history starts in the 1850s when people began to settle on the south side of Lake Apopka to grow citrus and other crops. Winter Garden became a mecca for the citrus and tourism industries, particularly fishing-related tourism as fishing in Lake Apopka was very popular. Winter Garden was connected to the world by rail. In fact, rail lines were built straight down the middle of Plant Street, Winter Garden's Main Street. The rail line was used to ship the citrus north and bring vacationers south. Historic Edgewater Hotel marketed itself to the fishers and even provided a boat to take fishers out on the lake as well as fish-cleaning stations and refrigerators for the fish on each floor. Eventually, Winter Garden's fortunes died out. Colonial Highway opened nearby and shopping and other commercial traffic moved there, nearly killing off the downtown. The city had made plans to tear down the Edgewater Hotel. However, locals came together to save and rehab it. That was the spark that lead to Winter Garden's renaissance.

Today, the downtown is vibrant with boutiques, cafes, recreation, and nightlife. The rail lines that cut through town are now part of the West Orange Trail. It's not uncommon to see bikers riding through the historic district. Winter Garden is located in West Orange County, Florida, approximately 15 miles west of downtown Orlando. The main commercial district lies along Plant Street between Dillard Street and Park Avenue with the intersection of Plant Street and Main Street serving as the heart of the historic district. One easy way to get there is to take the Plant Street exit off of toll road Florida State Road 429 and head west.

Photo Gallery Tour

We'll start our tour of Winter Garden, Florida at the intersection of Dillard Street and Plant Street. Winter Garden's Main Street is Plant Street. There is a Main Street as well nearby but that is more of side street compared to Plant Street. This is the First Baptist Church, built in 1922.
We'll start our tour of Winter Garden, Florida at the intersection of Dillard Street and Plant Street. Winter Garden's Main Street is Plant Street. There is a Main Street as well nearby but that is more of side street compared to Plant Street. This is the First Baptist Church, built in 1922.
Here we have the Winter Garden Heritage Museum. This complex contains a visitor center and gift shop. The building, constructed in 1918, originally served as a train depot for the Atlantic Cost Line Railroad.
Here we have the Winter Garden Heritage Museum. This complex contains a visitor center and gift shop. The building, constructed in 1918, originally served as a train depot for the Atlantic Cost Line Railroad.
Outside the Winter Garden Heritage Center is this caboose. It was built in 1948 and used on the Chesapeake and Ohio Railroad. Rail was important to Winter Garden as the area was one of the largest citrus producers in the country, shipping the citrus up north.
Outside the Winter Garden Heritage Center is this caboose. It was built in 1948 and used on the Chesapeake and Ohio Railroad. Rail was important to Winter Garden as the area was one of the largest citrus producers in the country, shipping the citrus up north.
If we pull back a bit, we can see the old railroad station. This was first used by the Orange Belt Railway, which eventually was incorporated into the Atlantic Coast Line Railroad.
If we pull back a bit, we can see the old railroad station. This was first used by the Orange Belt Railway, which eventually was incorporated into the Atlantic Coast Line Railroad.
On this tour we'll head west along Plant Street. The main commercial district lies along Plant Street between Dillard Street and Park Avenue. Plant Street is named for Henry B. Plant, a railroad tycoon known for connecting the isolated Tampa Bay area and southwest Florida to the nation's railroad system.
On this tour we'll head west along Plant Street. The main commercial district lies along Plant Street between Dillard Street and Park Avenue. Plant Street is named for Henry B. Plant, a railroad tycoon known for connecting the isolated Tampa Bay area and southwest Florida to the nation's railroad system.
We get to the corner of Plant Street and Main Street. If we head down Main Street we find some more shops and businesses. Many of these buildings were only recently rehabbed with new businesses pouring into them.
We get to the corner of Plant Street and Main Street. If we head down Main Street we find some more shops and businesses. Many of these buildings were only recently rehabbed with new businesses pouring into them.
Here we see some more of the businesses in historic buildings along Main Street. Notice that most of these buildings are brick. After a fire in 1909 wiped out most of the buildings, the city was rebuilt with brick.
Here we see some more of the businesses in historic buildings along Main Street. Notice that most of these buildings are brick. After a fire in 1909 wiped out most of the buildings, the city was rebuilt with brick.
Check out this cute wellness boutique along Main Street, painted in some bright colors.
Check out this cute wellness boutique along Main Street, painted in some bright colors.
This shop on Main Street sells gifts, jewelry, and apparel.
This shop on Main Street sells gifts, jewelry, and apparel.
More historic buildings along Main Street. In the background we have the Winter Garden water tower. Painted on the water tower, you can see the Centennial Clock Tower that is often used as a symbol of Winter Garden.
More historic buildings along Main Street. In the background we have the Winter Garden water tower. Painted on the water tower, you can see the Centennial Clock Tower that is often used as a symbol of Winter Garden.
We make it back to Plant Street. Here at the corner of Plant and Main, we see a cafe and a yoga studio. This building on the corner, constructed in 1912, was the first brick building built in Winter Garden after a 1909 fire destroyed most of the wooden structures in town.
We make it back to Plant Street. Here at the corner of Plant and Main, we see a cafe and a yoga studio. This building on the corner, constructed in 1912, was the first brick building built in Winter Garden after a 1909 fire destroyed most of the wooden structures in town.
This building was constructed in 1913 and was originally the site of the Shelby Hotel.
This building was constructed in 1913 and was originally the site of the Shelby Hotel.
Here is a view of the Centennial Clock Tower we mentioned earlier. Running down the middle of Plant Street is a hiking and biking trail that is part of the West Orange Trail. This is a rails to trails project. Originally rail lines along with trains ran down the middle of Plant Street. This well landscaped stretch is known as Centennial Plaza.
Here is a view of the Centennial Clock Tower we mentioned earlier. Running down the middle of Plant Street is a hiking and biking trail that is part of the West Orange Trail. This is a rails to trails project. Originally rail lines along with trains ran down the middle of Plant Street. This well landscaped stretch is known as Centennial Plaza.
As we continue down Plant Street, we find more restaurants, businesses, and even a bar, featuring live music.
As we continue down Plant Street, we find more restaurants, businesses, and even a bar, featuring live music.
On the left, the Roper Building was built in 1927 and was originally home to a hardware store.
On the left, the Roper Building was built in 1927 and was originally home to a hardware store.
It's not uncommon to see these little electric golf carts buzzing around town. In the background is the Edgewater Hotel, one of the most important buildings in Winter Garden. Years ago, when the community came together to prevent the tearing down of this building, they started something that lead to the preservation of the historic district.
It's not uncommon to see these little electric golf carts buzzing around town. In the background is the Edgewater Hotel, one of the most important buildings in Winter Garden. Years ago, when the community came together to prevent the tearing down of this building, they started something that lead to the preservation of the historic district.
Here is a view of an ice cream shop inside the Edgewater Hotel. Almost looks like an old timey soda fountain. Construction on the Edgewater Hotel began in 1924 and was completed in 1927.
Here is a view of an ice cream shop inside the Edgewater Hotel. Almost looks like an old timey soda fountain. Construction on the Edgewater Hotel began in 1924 and was completed in 1927.
This is the lobby of the Edgewater Hotel, which now operates as a bed and breakfast. Early in its life, the Edgewater was a place to stay for vacationers who came to fish in nearby Lake Apopka. The hotel advertised itself as a full-service fishing lodge, providing boat trips for fishers and cleaning stations and refrigerators for the fish on each floor.
This is the lobby of the Edgewater Hotel, which now operates as a bed and breakfast. Early in its life, the Edgewater was a place to stay for vacationers who came to fish in nearby Lake Apopka. The hotel advertised itself as a full-service fishing lodge, providing boat trips for fishers and cleaning stations and refrigerators for the fish on each floor.
This is the front desk of the Edgewater Hotel. Notice the antique cash register, safe, and switchboard amongst some other cool items. The Edgewater hosted the Washington Senators during their Spring Training, WWII troops, and even workers performing site work on the land that would become Walt Disney World before the hotel closed in 1968.
This is the front desk of the Edgewater Hotel. Notice the antique cash register, safe, and switchboard amongst some other cool items. The Edgewater hosted the Washington Senators during their Spring Training, WWII troops, and even workers performing site work on the land that would become Walt Disney World before the hotel closed in 1968.
Back outside, we can see Centennial Plaza along with a well-landscaped West Orange Trail, running through Plant Street. In the background is the Cappleman Building, built in 1921. At one time, it was known as the Clinic Building due to all the doctor's offices in it. Also the Winter Garden Post Office called this building home from 1933 to 1955.
Back outside, we can see Centennial Plaza along with a well-landscaped West Orange Trail, running through Plant Street. In the background is the Cappleman Building, built in 1921. At one time, it was known as the Clinic Building due to all the doctor's offices in it. Also the Winter Garden Post Office called this building home from 1933 to 1955.
The water fountain in the center of Centennial Plaza features mosaic tiles designed like old fruit-packing labels. A reminder of Winter Garden's past in the citrus industry.
The water fountain in the center of Centennial Plaza features mosaic tiles designed like old fruit-packing labels. A reminder of Winter Garden's past in the citrus industry.
We're looking at it from behind, but the sign reads Centennial Plaza. This plaza was dedicated in 2003.
We're looking at it from behind, but the sign reads Centennial Plaza. This plaza was dedicated in 2003.
If we head north on Boyd Street, we find this deli with outdoor seating. If you head a little further north, you'll find a convenient parking lot.
If we head north on Boyd Street, we find this deli with outdoor seating. If you head a little further north, you'll find a convenient parking lot.
Back on Plant Street, we find this row of shops on the ground floor of the Cappleman Building. On the corner is a bike shop. Biking is very popular in the area, and it's not uncommon to find bicyclists travelling through or stopping in town. You may even see some shopping and eating while wearing their biking attire.
Back on Plant Street, we find this row of shops on the ground floor of the Cappleman Building. On the corner is a bike shop. Biking is very popular in the area, and it's not uncommon to find bicyclists travelling through or stopping in town. You may even see some shopping and eating while wearing their biking attire.
Further down on Plant Street in the Cappleman Building, we find more shops, including several boutiques and furniture shops.
Further down on Plant Street in the Cappleman Building, we find more shops, including several boutiques and furniture shops.
We pull back and get another view of the Cappleman Building along this tree-lined stretch of Plant Street.
We pull back and get another view of the Cappleman Building along this tree-lined stretch of Plant Street.
Across the street, we have some more shops, including a chocolate shop (Yum!) and another bike shop. Customers line up at a carryout window for a new Winter Garden eatery.
Across the street, we have some more shops, including a chocolate shop (Yum!) and another bike shop. Customers line up at a carryout window for a new Winter Garden eatery.
We head south on Boyd Street and find more shops along the way.
We head south on Boyd Street and find more shops along the way.
Here on Boyd Street, we come to the Central Florida Railroad Museum. This was originally the Tavares & Gulf Railroad Depot built in 1913. In the background, we can see the Winter Garden water tower with its famous Centennial Clock Tower painted on it.
Here on Boyd Street, we come to the Central Florida Railroad Museum. This was originally the Tavares & Gulf Railroad Depot built in 1913. In the background, we can see the Winter Garden water tower with its famous Centennial Clock Tower painted on it.
We head back to Plant Street where we find some more businesses, including a cafe, housed in some excellent historic architecture.
We head back to Plant Street where we find some more businesses, including a cafe, housed in some excellent historic architecture.
Space between two buildings serves as a walkway and also provides an area for folks dining outdoors.
Space between two buildings serves as a walkway and also provides an area for folks dining outdoors.
Here is another view looking back towards Plant Street. Here we see some boutiques along with eateries. In Winter Garden, even the alleys are buzzing with activity.
Here is another view looking back towards Plant Street. Here we see some boutiques along with eateries. In Winter Garden, even the alleys are buzzing with activity.
Back on Plant Street, we see all kinds of fun things to do. On the left is a nightclub, featuring live music. On the right is an historical theater that still hosts performances and movies. The Garden Theatre was built in 1935 as a single-screen cinema but closed in 1963. It was eventually rehabilitated and reopened in 2008.
Back on Plant Street, we see all kinds of fun things to do. On the left is a nightclub, featuring live music. On the right is an historical theater that still hosts performances and movies. The Garden Theatre was built in 1935 as a single-screen cinema but closed in 1963. It was eventually rehabilitated and reopened in 2008.
Across the street, we see more restaurants with outdoor seating and even a gourmet shop.
Across the street, we see more restaurants with outdoor seating and even a gourmet shop.
Further down on Plant Street, we find another boutique and a French cafe.
Further down on Plant Street, we find another boutique and a French cafe.
On the other side of Plant Street, we find a splash pad to help keep the kids entertained and cooled off.
On the other side of Plant Street, we find a splash pad to help keep the kids entertained and cooled off.
Also in this immediate area, we find a new parking garage. Much needed in the area. Certain times of the week, such as during the Farmer's Market, parking can be tight. In fact, in the foreground of this picture we can see the Farmer's Market in full swing.
Also in this immediate area, we find a new parking garage. Much needed in the area. Certain times of the week, such as during the Farmer's Market, parking can be tight. In fact, in the foreground of this picture we can see the Farmer's Market in full swing.
Here is another view of the Winter Garden Farmer's Market. Local merchants sell gifts, crafts, foods, and fresh produce. There's also live music.
Here is another view of the Winter Garden Farmer's Market. Local merchants sell gifts, crafts, foods, and fresh produce. There's also live music.
Underneath the pavillion, we have another shot of the Farmer's Market. Here is where a lot of the fresh produce is sold. Also, in the pavillion are public restrooms.
Underneath the pavillion, we have another shot of the Farmer's Market. Here is where a lot of the fresh produce is sold. Also, in the pavillion are public restrooms.
If we continue down Plant Street, we start to pass some government buildings such as this Post Office.
If we continue down Plant Street, we start to pass some government buildings such as this Post Office.
Next door to the Post Office is the Winter Garden Police Station.
Next door to the Post Office is the Winter Garden Police Station.
This is the Winter Garden City Hall recently built in 2008 to help support the fast growing city.
This is the Winter Garden City Hall recently built in 2008 to help support the fast growing city.
Further down, we have some newer commercial structures that help extend the activity further west along Plant Street.
Further down, we have some newer commercial structures that help extend the activity further west along Plant Street.
Here is a rear view shot of the building we looked at in the previous picture. As you can see, there are additional restaurants back here as well as more parking.
Here is a rear view shot of the building we looked at in the previous picture. As you can see, there are additional restaurants back here as well as more parking.
Next door is the Plant Street Market. It's a new building but has the feeling of a rehabbed historic structure. It's a huge draw for the area. The Market includes small shops, eateries, and even a microbrewery.
Next door is the Plant Street Market. It's a new building but has the feeling of a rehabbed historic structure. It's a huge draw for the area. The Market includes small shops, eateries, and even a microbrewery.
Here is an interior view of the Plant Street Market. You can see the wide variety of local vendors. There's also places to sit inside the market and outside as well.
Here is an interior view of the Plant Street Market. You can see the wide variety of local vendors. There's also places to sit inside the market and outside as well.
Towards the back of the Plant Street Market is a popular microbrewery.
Towards the back of the Plant Street Market is a popular microbrewery.
We head outside and conclude our tour with one more scene from the Plant Street Market. On a gorgeous day, there are plenty of places to sit and eat after patronizing the local businesses inside.
We head outside and conclude our tour with one more scene from the Plant Street Market. On a gorgeous day, there are plenty of places to sit and eat after patronizing the local businesses inside.

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