Destination Main Streets

Winter Park, Florida

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Park Avenue, or "Park Ave" as the locals call it, is the Main Street and focal point of downtown Winter Park, Florida. In fact, just a few miles north of downtown Orlando, Park Avenue serves as a major retail and dining mecca for all of Central Florida. And if anyone doubted the city's cosmopolitan focal point for the Orlando metro area, Winter Park boasts several major museums and even its own Amtrak station that is also a stop on the SunRail, Central Florida's commuter rail line. Also, Rollins College, Florida's oldest recognized college, is located at the southern end of Park Avenue, which gives Winter Park a dynamic, college town feel. Winter Park was originally founded as a winter resort for wealthy northerners, hence the name. And wealth is still a key ingredient in Winter Park's mix. The city is one of the wealthiest in the area. Therefore, the shops in downtown Winter Park tend to be more upscale to meet the tastes of the area's well-to-do residents.

Although, Park Avenue is the central artery through town, other businesses can be found on side streets including East Morse Avenue, and East Lyman Avenue. More businesses are located in the Hannibal Square district, on West New England Avenue between Virginia and Pennsylvania Avenues within walking distance of Park Avenue. Although Fairbanks Avenue is not as pedestrian friendly as the rest of Winter Park, many unique shops and restaurants can be found along this stretch as well. Winter Park is an independent city in Orange County, Florida just outside of the city of Orlando. Its downtown is about seven miles away from downtown Orlando. Other nearby Main Street communities in the city of Orlando include College Park and Ivanhoe Village. Also, in the Central Florida area, you have Sanford, Celebration, and Mount Dora.

Photo Gallery Tour

Today, we'll start our tour of Winter Park, Florida at the south end of Park Avenue where Park Avenue meets Fairbanks Avenue and work our way north along Park Avenue.  Park Avenue is Winter Park's Main Street.  Here, south of Fairbanks Avenue, we see Rollins College, which makes its home in Winter Park.
Today, we'll start our tour of Winter Park, Florida at the south end of Park Avenue where Park Avenue meets Fairbanks Avenue and work our way north along Park Avenue. Park Avenue is Winter Park's Main Street. Here, south of Fairbanks Avenue, we see Rollins College, which makes its home in Winter Park.
We head north along Park Avenue or "Park Ave" as the locals call it.  There aren't too many chains on Park Avenue but this one is an exception and not too far from Rollins College at that.
We head north along Park Avenue or "Park Ave" as the locals call it. There aren't too many chains on Park Avenue but this one is an exception and not too far from Rollins College at that.
Up ahead and across the street are more shops and boutiques.  The brick paved streets are very common throughout the Orlando area.
Up ahead and across the street are more shops and boutiques. The brick paved streets are very common throughout the Orlando area.
As we continue along Park Avenue we find several shops and restaurants, including a French bistro and an Italian restaurant.  Winter Park is known for its culinary diversity.
As we continue along Park Avenue we find several shops and restaurants, including a French bistro and an Italian restaurant. Winter Park is known for its culinary diversity.
More shops along Park Avenue.  This one has a kitschy feel to it.  Park Avenue gets its name from the large Central Park that runs along Park Avenue that we will be seeing in a little bit.
More shops along Park Avenue. This one has a kitschy feel to it. Park Avenue gets its name from the large Central Park that runs along Park Avenue that we will be seeing in a little bit.
We get to the corner of Park Avenue and Comstock Avenue.  This appliance store is in a fun-looking art deco building.
We get to the corner of Park Avenue and Comstock Avenue. This appliance store is in a fun-looking art deco building.
Across the street is a Restoration Hardware.  Although there aren't too many restaurant chains in Winter Park some retail chains have set up shop in this upscale shopping district.
Across the street is a Restoration Hardware. Although there aren't too many restaurant chains in Winter Park some retail chains have set up shop in this upscale shopping district.
Speaking of chains, here are a few more examples in this building that gently curves as Park Avenue curves slightly as well.
Speaking of chains, here are a few more examples in this building that gently curves as Park Avenue curves slightly as well.
Throughout Winter Park's downtown are these interesting art nouveau style information kiosks with electronic touch screen displays.
Throughout Winter Park's downtown are these interesting art nouveau style information kiosks with electronic touch screen displays.
We make it to the corner of Park Avenue and Lyman Avenue and we see the Winter Park City Hall.  The City Hall actually takes up the entire block between Comstock and Lyman but this shot is from Lyman Avenue.
We make it to the corner of Park Avenue and Lyman Avenue and we see the Winter Park City Hall. The City Hall actually takes up the entire block between Comstock and Lyman but this shot is from Lyman Avenue.
And this is a view of the boutiques and eateries catty-corner from the City Hall on the other side of Park Avenue and Lyman Avenue.
And this is a view of the boutiques and eateries catty-corner from the City Hall on the other side of Park Avenue and Lyman Avenue.
Here are more shops and businesses along Park Avenue.  In Winter Park, and many other cities in Florida, you see these signs on the sidewalks pointing to the shops along the street.
Here are more shops and businesses along Park Avenue. In Winter Park, and many other cities in Florida, you see these signs on the sidewalks pointing to the shops along the street.
More boutique shopping along the tree lined streets of Park Avenue in Winter Park, Florida.
More boutique shopping along the tree lined streets of Park Avenue in Winter Park, Florida.
More shops, including a cigar shop, and an outdoor cafe along Park Avenue in Winter Park, Florida.
More shops, including a cigar shop, and an outdoor cafe along Park Avenue in Winter Park, Florida.
The Colony Theater opened in the 1940s and lasted until 1975 when it was put out of business by larger movie chains.  The building was used to house smaller shops and restaurants until 1999 when Pottery Barn renovated and moved in.
The Colony Theater opened in the 1940s and lasted until 1975 when it was put out of business by larger movie chains. The building was used to house smaller shops and restaurants until 1999 when Pottery Barn renovated and moved in.
We continue heading north along Park Avenue where we find more boutiques in downtown Winter Park, Florida.
We continue heading north along Park Avenue where we find more boutiques in downtown Winter Park, Florida.
Across the street we find more shops, restaurants, and even a mid rise office building all in downtown Winter Park, Florida.
Across the street we find more shops, restaurants, and even a mid rise office building all in downtown Winter Park, Florida.
We see a pharmacy and a candy shop.  In the distance is the intersection of Park Avenue with New England Avenue.  We also see a sign pointing to Hannibal Square and the Winter Park History Museum, which we will be visiting in a moment.
We see a pharmacy and a candy shop. In the distance is the intersection of Park Avenue with New England Avenue. We also see a sign pointing to Hannibal Square and the Winter Park History Museum, which we will be visiting in a moment.
At the corner of Park Avenue and New England Avenue is this interesting building, which contains a lot of greenery on its second floor.
At the corner of Park Avenue and New England Avenue is this interesting building, which contains a lot of greenery on its second floor.
We'll take our first detour off Park Avenue and head down New England Avenue towards Hannibal Square.  New England Avenue is the southern boundary of Central Park (where Park Avenue gets its name).  This is our first shot of Central Park.  Notice the peacock.  It's the symbol of Winter Park and it's not uncommon to see them running wild from time to time.
We'll take our first detour off Park Avenue and head down New England Avenue towards Hannibal Square. New England Avenue is the southern boundary of Central Park (where Park Avenue gets its name). This is our first shot of Central Park. Notice the peacock. It's the symbol of Winter Park and it's not uncommon to see them running wild from time to time.
As we head west on New England Avenue, we pass the Winter Park History Museum.  It is one of several museums in the Winter Park area and is located in a former railroad freight depot.  Every Saturday behind the museum is the Winter Park Farmers' Market.
As we head west on New England Avenue, we pass the Winter Park History Museum. It is one of several museums in the Winter Park area and is located in a former railroad freight depot. Every Saturday behind the museum is the Winter Park Farmers' Market.
We head a couple more blocks down New England Avenue before entering the Hannibal Square district.  Here we find some elegant buildings housing a wide array of businesses.
We head a couple more blocks down New England Avenue before entering the Hannibal Square district. Here we find some elegant buildings housing a wide array of businesses.
More shops and a coffee shop where I had stepped in on a hot day for something to drink.  Hannibal Square had been a segregated African-American neighborhood in West Winter Park.  Today it is home to the Hannibal Square Heritage Center, which preserves the history of the African-American community.
More shops and a coffee shop where I had stepped in on a hot day for something to drink. Hannibal Square had been a segregated African-American neighborhood in West Winter Park. Today it is home to the Hannibal Square Heritage Center, which preserves the history of the African-American community.
A newer building along New England Avenue.  Here we see businesses along the bottom and residences on the upper floors.
A newer building along New England Avenue. Here we see businesses along the bottom and residences on the upper floors.
Across the street are multiple restaurants with wide sidewalks for outdoor dining in Hannibal Square.
Across the street are multiple restaurants with wide sidewalks for outdoor dining in Hannibal Square.
We get to the corner of New England Avenue and Hannibal Square.  This fine looking building has excellent stone work and wooden shutters.  Looks like it houses a French restaurant with what appears to be outdoor seating on two stories.
We get to the corner of New England Avenue and Hannibal Square. This fine looking building has excellent stone work and wooden shutters. Looks like it houses a French restaurant with what appears to be outdoor seating on two stories.
We get to Shady Park, another large park in the city of Winter Park where we see this monument to Hannibal Square.
We get to Shady Park, another large park in the city of Winter Park where we see this monument to Hannibal Square.
Here is a view looking southbound down Pennsylvania Avenue at some of the restaurants and other businesses in the Hannibal Square area of Winter Park.  From here, we will head back to Park Avenue.
Here is a view looking southbound down Pennsylvania Avenue at some of the restaurants and other businesses in the Hannibal Square area of Winter Park. From here, we will head back to Park Avenue.
We are back on Park Avenue.  From here, we will continue our tour of Winter Park by heading north.  The Wine Room showcases over 150 hand-selected wines that can be sampled from wine dispensing machines.
We are back on Park Avenue. From here, we will continue our tour of Winter Park by heading north. The Wine Room showcases over 150 hand-selected wines that can be sampled from wine dispensing machines.
More shops and businesses along Park Avenue in Winter Park.  You can't see it in this shot but Central Park is across the street.  So for awhile most of these shots will show the shops, restaurants, and businesses on the east side of Park Avenue while Central Park will be on the west side of Park Avenue.
More shops and businesses along Park Avenue in Winter Park. You can't see it in this shot but Central Park is across the street. So for awhile most of these shots will show the shops, restaurants, and businesses on the east side of Park Avenue while Central Park will be on the west side of Park Avenue.
And if you look across the street, you will see Central Park.  Here is a view of the park near where Welbourne Avenue meets with Park Avenue.
And if you look across the street, you will see Central Park. Here is a view of the park near where Welbourne Avenue meets with Park Avenue.
This is a view of the intersection of Park Avenue with Welbourne Avenue.  There is a sign pointing to more shops down Welbourne Avenue.  The sign says East Welbourne Shops.
This is a view of the intersection of Park Avenue with Welbourne Avenue. There is a sign pointing to more shops down Welbourne Avenue. The sign says East Welbourne Shops.
So let's head down Welbourne Avenue in Winter Park where we cone across this book store.
So let's head down Welbourne Avenue in Winter Park where we cone across this book store.
At the corner of Welbourne Avenue and Center Street in Winter Park we find this Mexican restaurant.
At the corner of Welbourne Avenue and Center Street in Winter Park we find this Mexican restaurant.
We head back out to Park Avenue.  This is a view of Park Avenue from Central Park in Winter Park, Florida.
We head back out to Park Avenue. This is a view of Park Avenue from Central Park in Winter Park, Florida.
As we continue heading north on Park Avenue in Winter Park, we find more shops, boutiques, and sidewalk cafes.
As we continue heading north on Park Avenue in Winter Park, we find more shops, boutiques, and sidewalk cafes.
Up ahead is a sign pointing into a courtyard filled with more shops and cafes.  This courtyard is called Greeneda Court.
Up ahead is a sign pointing into a courtyard filled with more shops and cafes. This courtyard is called Greeneda Court.
Here is another view looking into the interior of Greeneda Court and its shops, eateries, and other services.  We'll see a few other courtyards like this along Park Avenue in Winter Park.  Also, on Park Avenue we see quite a few financial services firms.
Here is another view looking into the interior of Greeneda Court and its shops, eateries, and other services. We'll see a few other courtyards like this along Park Avenue in Winter Park. Also, on Park Avenue we see quite a few financial services firms.
At this point, we'll head across Central Park and check out the SunRail station with its art nouveau architecture.  Winter Park has long been known for its stop on a rail line.  It has had stations going back to 1882.  This current station was built in 2014 and serves the SunRail commuter line and Amtrak as well.
At this point, we'll head across Central Park and check out the SunRail station with its art nouveau architecture. Winter Park has long been known for its stop on a rail line. It has had stations going back to 1882. This current station was built in 2014 and serves the SunRail commuter line and Amtrak as well.
Now we'll head back to the shopping again. This time on the other side of Park Avenue on Morse Boulevard.  Morse has a wide, tree-lined median with shops and eateries on either side.
Now we'll head back to the shopping again. This time on the other side of Park Avenue on Morse Boulevard. Morse has a wide, tree-lined median with shops and eateries on either side.
Here's another view of Morse Boulevard with its shops and other services in Winter Park, Florida.
Here's another view of Morse Boulevard with its shops and other services in Winter Park, Florida.
We head further down Morse Boulevard in Winter Park to find folks walking along the sidewalk and others eating at an outdoor cafe.
We head further down Morse Boulevard in Winter Park to find folks walking along the sidewalk and others eating at an outdoor cafe.
Back on Park Avenue we find more shops and boutiques, including some well known chains.
Back on Park Avenue we find more shops and boutiques, including some well known chains.
As we continue heading north along Park Avenue in Winter Park, we find more shops and restaurants, some with outdoor seating on the wide sidewalks.
As we continue heading north along Park Avenue in Winter Park, we find more shops and restaurants, some with outdoor seating on the wide sidewalks.
More chains and financial services can be found in this building with some interesting modern architecture on Park Avenue.
More chains and financial services can be found in this building with some interesting modern architecture on Park Avenue.
We take a break for a view across the street at Central Park at a fountain as well as some lush landscaping.
We take a break for a view across the street at Central Park at a fountain as well as some lush landscaping.
Also, in Central Park you can see one of Winter Park's electronic information kiosks.  Notice the Spanish moss hanging from the trees.  The crosswalk is where Park Avenue meets Lincoln Avenue.
Also, in Central Park you can see one of Winter Park's electronic information kiosks. Notice the Spanish moss hanging from the trees. The crosswalk is where Park Avenue meets Lincoln Avenue.
More shops and restaurants along Park Avenue.  On the right, you can see more of those signs that point out the location of businesses.  Also, in this mix is the Shops on Park indoor mall.
More shops and restaurants along Park Avenue. On the right, you can see more of those signs that point out the location of businesses. Also, in this mix is the Shops on Park indoor mall.
This is a view inside the Shops on Park indoor mall.  They have shops, eateries, and even a koi pond.  I did find a public bathroom here, by the way.
This is a view inside the Shops on Park indoor mall. They have shops, eateries, and even a koi pond. I did find a public bathroom here, by the way.
More shops and restaurants on Park Avenue in Winter Park.  A lot of people were lined up for brunch outside of the Briarpatch when I took this picture.
More shops and restaurants on Park Avenue in Winter Park. A lot of people were lined up for brunch outside of the Briarpatch when I took this picture.
Another view of a wide variety of shops, services, and eateries on Park Avenue in Winter Park, Florida.
Another view of a wide variety of shops, services, and eateries on Park Avenue in Winter Park, Florida.
We get to the corner of Park Avenue and Garfield Avenue.  Garfield is the northern boundary of Central Park.  We are actually looking at shops now on the west side of Park Avenue.
We get to the corner of Park Avenue and Garfield Avenue. Garfield is the northern boundary of Central Park. We are actually looking at shops now on the west side of Park Avenue.
And now we're back on the east side of Park Avenue again.  Here we see some more shops, including another courtyard entrance.  This one is called Hidden Garden.
And now we're back on the east side of Park Avenue again. Here we see some more shops, including another courtyard entrance. This one is called Hidden Garden.
This is a view inside the Hidden Garden courtyard where we see some shops, trees, benches, and a fountain.
This is a view inside the Hidden Garden courtyard where we see some shops, trees, benches, and a fountain.
We head back out and find more shops on Park Avenue.  Some of these boutiques are even having a sidewalk sale.
We head back out and find more shops on Park Avenue. Some of these boutiques are even having a sidewalk sale.
Some more shops, restaurants, and businesses on Park Avenue.  We see some more of those cool business signs and even another entrance to the Hidden Garden courtyard.
Some more shops, restaurants, and businesses on Park Avenue. We see some more of those cool business signs and even another entrance to the Hidden Garden courtyard.
We head back down into the courtyard and find a boutique and an eatery with outdoor seating in this part of the Hidden Garden.
We head back down into the courtyard and find a boutique and an eatery with outdoor seating in this part of the Hidden Garden.
Across the street on the other side of Park Avenue are some more shops and restaurants in these upscale mid-rise buildings in Winter Park.
Across the street on the other side of Park Avenue are some more shops and restaurants in these upscale mid-rise buildings in Winter Park.
This is another view of the boutique shopping along this stretch of Park Avenue in Winter Park, Florida.
This is another view of the boutique shopping along this stretch of Park Avenue in Winter Park, Florida.
We get to the corner of Park Avenue and Canton Avenue.  This is the northern limit of the heaviest shopping in downtown Winter Park.
We get to the corner of Park Avenue and Canton Avenue. This is the northern limit of the heaviest shopping in downtown Winter Park.
Across the street, just south of Canton Avenue are more shops and restaurants along Park Avenue in Winter Park.
Across the street, just south of Canton Avenue are more shops and restaurants along Park Avenue in Winter Park.
Heading north on the other side of Canton Avenue is St. Margaret Mary Catholic Church.
Heading north on the other side of Canton Avenue is St. Margaret Mary Catholic Church.
And just so we cover all four corners here, on the northwest corner is the Morse Museum, which houses the world's most comprehensive collection of works by Louis Comfort Tiffany, including the artist and designer's jewelry, pottery, paintings, and other works.  The museum also contains other American works of art.  This is one of the many museums in the Winter Park area.
And just so we cover all four corners here, on the northwest corner is the Morse Museum, which houses the world's most comprehensive collection of works by Louis Comfort Tiffany, including the artist and designer's jewelry, pottery, paintings, and other works. The museum also contains other American works of art. This is one of the many museums in the Winter Park area.
If we head a little bit further north on Park Avenue, we'll find a few more shops and businesses such as these in this Brandywine Square shopping center.  Past this it becomes mostly residential so at this point, we will end our tour and rest our feet.
If we head a little bit further north on Park Avenue, we'll find a few more shops and businesses such as these in this Brandywine Square shopping center. Past this it becomes mostly residential so at this point, we will end our tour and rest our feet.

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