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Interlachen Avenue Historic District

5.0 (1 review)

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Hannibal Square

Hannibal Square

4.3(6 reviews)
0.5 mi

Hannibal Square is a historic district in Winter Park on New England Avenue two blocks west of Park…read moreAvenue, between Virginia and Pennsylvania Avenues. Winter Park sprang up around a railroad track laid in 1880 by the South Florida Railroad that connected Orlando to Sanford. Hannibal Square was founded in 1881 as an African-American community of laborers who built the town and worked as domestic servants to the areas wealthy families. The people who lived in Hannibal Square had educational opportunities, prosperity, and professional standing. The railroad tracks served as the dividing line in the town with whites living on the east side and blacks to the west. While visiting Hannibal Square I enjoyed taking in the charming architecture, Shady Park, the Hannibal Square Heritage Center, restaurants, and shops. Hannibal Square is not as busy as the Park Ave area of town but it is still near enough to it that you could easily walk there.

2019 Review 47/100 A…read moregreat little area in Winter Park. Worth stopping by if you're strolling down Park Ave (it's only a few blocks away). Hannibal Square is lined with a variety of great restaurants and cool shops (Rifle Paper Co. is my fave!). It's much smaller than Park Ave. And almost never as crowded. So it's great if you're looking for a chill "Winter Park experience" without the hustle and bustle of Park Ave. Plus parking is always much easier. I usually park in Hannibal Square on Saturday mornings and go for a nice run through the Square up to Park Ave and walk around the Winter Park Farmers' Market.

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Hannibal Square
Hannibal Square
Hannibal Square

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Washington Street Bridge

Washington Street Bridge

5.0(2 reviews)
3.8 mi•Lawsona / Fern Creek

Stopping for a minute to read a historic marker is a great way to learn more about the history of…read morean area. I have learned so much from these blue historical markers that can you find all around the state. This particular marker is located in H.H. Dickinson Azalea Park. One side of the marker tells about the park and the other side is about the nearby Washington Street Bridge. During the 1920's, Florida experienced a massive period of growth called the land boom years. As growth moved east in Orlando the little wooden bridge over Fern Creek could no longer with stand the increased vehicle traffic. In July of 1926, the Orlando City Council accepted proposals to replace the bridge. Concrete Steel Bridge Company of Miami Beach was chosen for their $10,400 bid. Orlando City Engineer Morton Hagartney designed a reinforced concrete arch deck bridge with walkways on both sides. The historically inspired light fixtures give the bridge its classical appearance. The bridge isn't very large but it is very pretty and is great for pictures, especially by the lamp posts. The Washington Street Bridge is the only bridge of its kind in the City of Orlando and was designated a Historic Landmark by the city in 1991. In 2014, historic marker F-808 was installed by The City of Orlando District 4 Commissioner Parry Sheehan, Girl Scouts of Citrus Council, Orlando Garden Club, Lake Lawsona Fern Creek Historical Neighborhood Association, Eugene & Lois Pawlak & Family, Dr. Howard Green & Family, The Van De Bogert Family, Deborah Kohan, The Magley Family, Robin & Nancy Lewis, Nancy & Walk Jones, Kathy Wickman, Theresa Smith and the Florida Department of State.

I love discovering these little historical markers that you can see in every city and town across…read morethe country. By seeing the blue historical sign, I learned a little bit more about the history of Orlando. The Washington Street bridge is located on the corner of Washington Street and Rosearden Drive in the downtown section of Orlando. It is right next to Dickson Azalea Park and this new bridge is going on one hundred years old. The bridge was built back in 1926 to replace a deteriorating wooden bridge over Fern Creek and was built for the sum of $10,400. Today, it is the only Bridge of its kind here in Orlando and was designated a Historic Landmark by the city back in 1991. It is hard to imagine what Orlando was like back in 1926. However, this bridge gives us a glimpse of that moment in history. How many people have walked across this bridge since its opening? Orlando is a city that continues to change and progress, but we can never lose sight of the past of the city.

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Washington Street Bridge
Washington Street Bridge
Washington Street Bridge

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Downtown Winter Park Historic District - The annual Christmas parade.

Downtown Winter Park Historic District

4.9(14 reviews)
0.2 mi

The Winter Park Downtown Historic District is a fantastic neighborhood with its roots tracing back…read moreto 1881. The neighborhood has some great restaurants and shopping options and is close enough to downtown Orlando to make it convenient, yet far enough away to embrace its own identity and be a lot more laid back. The streets are cobblestone and just adds to the ambiance. This is a nice upscale neighborhood and gives a cool, almost small-town feel in the midst of the city of Orlando, Florida. I would definitely recommend a visit to this cool neighborhood.

Winter Park began as 8 acres of land purchased by David Mizoram Jr. in 1858 who called his purchase…read moreLakeview. The town of Winter Park was plotted when Loring Chase and Oliver Chapman purchased 600 acres in 1881. Life was given to the new town when the railroad was persuaded to extend it's line. The railroad depot built in 1882 was the towns first building. A store was built at Park Ave and Morse Blvd that housed a mercantile, post office, and assembly room. The building still stands. The town was chartered in 1887 and became a retreat for wealthy northerners looking to escape the cold climate in the winter, hence the name of the town Winter Park. The towns economy was built on entertaining winter tourists. Rollins College, the oldest college in Florida was founded here in 1885. The city was incorporated in 1925 and is governed by four city commissioners and a mayor. Today Winter Park is 9 square miles and home to approximately 28,500 residents. The town is known for it's lakes, parks, museums, and shops and restaurants along historic Park Avenue. My favorite restaurant is the Briar Patch. The Winter Park Historic District includes buildings constructed from 1882 through 1965, and it runs along Park Avenue from Canton to Comstock Avenues. Winter Park has held on to its old small town charm. Popular past times here include a boat ride on Lake Osceola, a meal on Park Avenue, and a trip to the Morse Museum. Favorite festivals include the Winter Park Sidewalk Art Festival and the 4th of July Celebration in Central Park. The Winter Park Historic District is a delightful mixture of the new and the old and just like in the 1800's you can still arrive by train.

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Downtown Winter Park Historic District
Downtown Winter Park Historic District
Downtown Winter Park Historic District

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Harry P Leu Gardens - New cafe! Can't wait to come here to get some work done

Harry P Leu Gardens

4.5(382 reviews)
2.1 mi

These bots ticks gardens is such a beautiful conservatory of a lot of amazing floral and plant…read morespecies. You can take your time and stroll through the gardens or come or one of their many events they hose such as outdoor movie nights! Check their website and calendar to see when you'll want to stop by

I had to schedule some activities on non-theme park days, found Harry P Leu Gardens as an option,…read moreand it was one of our favorite visits. They host various exhibits at different times of the year to keep things fresh. I was there for Origami in the Garden, which ran from February to September last year, and they had 13 different origami sculptures scattered around the gardens. We got lucky for parking, which seemed plenty, but the gardens was host to several private celebratory events. The people at the welcome center were very friendly and informative, letting me know where to go and giving me useful guides. There's also a small cafe and marketplace before you make your way to the gardens. Overall, the grounds has a fair ratio of both shaded and unshaded areas with different plant species organized in some manner that goes beyond my understanding. You MUST make sure you are well protected by the UV, as it bears down. You should consider thirst quenchers, too. It wasn't too crowded, and there's plenty of semi-secluded spots for a peaceful picnic. I loved that the origami exhibits allowed us to have goals along the grounds. If I go here again, I'd be interested in touring the historic Leu house. The "secret garden" was not really anything except a bunch of foliage, in my opinion, so it was kind of a waste of time trying to find it. The map is very helpful, and the paths are distinguished enough to not get lost. It looks like they had several beautiful options for wedding venues. The Leu Gardens is a great place to pair with some downtown Orlando or Winter Park exploration.

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Harry P Leu Gardens - Jazz and Blues Concert

Jazz and Blues Concert

Harry P Leu Gardens - Glass exhibit ANTS

Glass exhibit ANTS

Harry P Leu Gardens - Proposal @maryfoskyphotography

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Proposal @maryfoskyphotography

Winter Park Telephone Company Historical Sign

Winter Park Telephone Company Historical Sign

5.0(2 reviews)
0.3 mi

I love finding a historical marker. Usually they are the blue state issued historic markers but the…read moreCity of Winter Park has installed several of their own markers at spots significant to the history of the city. This particular marker provides information about the Winter Park Telephone Company. You can the marker on South New York Avenue, on the right when traveling south. The Winter Park Telephone Company was established in 1910 in Maitland by Carl H. Galloway when his former boss in Texas sent him a used switchboard and ten used telephones. He installed the switchboard above his parents' general store and the phones found their way into the homes of nine wealthy families and a livery stable. At first Galloway provided phone service for free to promote the grocery business and customers enjoyed the convenience of phoning in their orders. By the next year business doubled to 20 phone customers. In 1912, another switchboard was installed in Winter Park in the Henkel Building at the corner of New England and Park Avenues. In 1913 the first telephone directory was published on one sheet of paper with 60 listings. In 1918 the company built its first plant on New England Avenue and named the company the Winter Park Telephone Company. The first phone cable was laid underground in order to preserve the natural beauty of Winter Park. Winter Park's 10,000th telephone was installed in 1956, and in 1966 the Winter Park Telephone Company became the first company in the Southeast to offer "Tel-Tone" pushbutton calling service. It was the tenth largest non-Bell telephone company in the country when it joined United Telephone System in 1979. Presently the company is named Sprint Corporation. If this marker sparks your curiosity, you can learn more about the historic Winter Park Telephone Company at the Maitland Art and History Museum where there is a display of antique phones and switchboards.

This historical sign is located between Century Link and the Lash Lounge and commemorates the…read moreWinter Park Telephone Company and its origins in 1910 as a telephone switchboard above a grocery store. Florida and the world certainly has changed since 1910, but it is important to remember our past.

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Winter Park Telephone Company Historical Sign
Winter Park Telephone Company Historical Sign
Winter Park Telephone Company Historical Sign

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Interlachen Avenue Historic District - landmarks - Updated May 2026

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