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    9 months ago

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    Hannibal Square

    Hannibal Square

    4.3(6 reviews)
    1.9 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)
    5.4 miLawsona / 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)
    1.9 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(386 reviews)
    3.6 mi

    If you're visiting Orlando, I highly recommend this as one of your stops. A historical landmark of…read morethe city. I found out the Leu family donated their family land hoping to share its beauty. Unique gardens with plenty of shade. Great for all ages, including toddlers. It is fenced in with lots of areas to picnic, if that's your thing! There's a small cafe for coffee, ice cream and a few snacks. On certain days they have infant and toddler reading time (20minutes long). The first Monday of each month is free entry however there are no guided tours. Check their website for more info!

    This garden is huge with wide paths through all the gardens with optional dirt paths. Most paths…read moreare naturally shaded by the tall mature live oak, cypress, crepe myrtle and banyan trees. If you love nature, you are in for a special treat as this garden has hundreds of plants and flowers all very clearly labeled. Sprinkled throughout the paths are funky bird houses and information on the birds there which sing non-stop in the background which is mesmerizing to sit on a bench by the brook and listen to birds and water, like I said, a special treat. I located a new bird to me, the gila woodpecker! The house museum tour is full of local Florida history and the house is beautiful with many interesting details like the children's back stairs and the bathrooms have original tiles and fixtures! The bathrooms are accessible, clean and well stocked with supplies. The map gives a clear idea of where you want to wander to and where you might want to stop to take in nature. One of my favorite places with sculpture added to the gardens along with specialized gardens for cocktail ingredients, salsa garden, chutney garden and tea garden! Fun! Many fruits and herbs as well. A must see if you love the outdoors, birds, plants, flowers, gardening or the peace that nature brings. A must see!!!!

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    Harry P Leu Gardens - Jazz and Blues Concert

    Jazz and Blues Concert

    Harry P Leu Gardens - Reading time

    Reading time

    Harry P Leu Gardens - Glass exhibit ANTS

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    Glass exhibit ANTS

    Lake Lily Drive

    Lake Lily Drive

    5.0(1 review)
    0.0 mi

    While taking a stroll along Lake Lily I was delighted to spot this historic marker recounting…read morehistorical information about the path I was on. Stopping for a minute to read a historic marker is a great way to learn more about the history of an area. I have gained so much knowledge about Florida from these blue historical markers that can you find all around the state. This marker is next to Lake Lily near the playground. According to the marker, the brick road along the west side of Lake Lily dates back to the Second Seminole War. In the 1830's Lake Lily Drive was used as part of the route between the Fort Mellon, a supply depot in Sanford along the St. Johns River and Fort Maitland built in 1838 on the shores of Lake Maitland across the street from this park. It took a full day by foot for troops to travel between the two forts. This small trail was important because it connected Fort Maitland to the main route. After leaving Lake Lily the route headed south south on what is now Highway 17-92. Lake Lily Drive became part of the first direct route from northeast Florida to Maitland. In 1915 Lake Lily Drive was covered in bricks making it the first grouted brick route in Florida. In 1925 Lake Lily Drive became part of Dixie Hwy connecting Sault Ste. Marie, Michigan to Miami, Florida. In 1927 the road was joined to the Black Bear Trail at Lake Lily. In the 1960's Lake Lily Drive was paved. A restoration project in 1998 removed the asphalt and the Maitland Historical Society restored the bricks. Today visitors to Lake Lily Park can take a step back in time as they walk along the brick pathway from the 1800's. Marker F-523 was installed in the park in 2004 by the City of Maitland and Florida Department of State.

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    Lake Lily Drive
    Lake Lily Drive
    Lake Lily Drive

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    Interlachen Avenue Historic District

    Interlachen Avenue Historic District

    5.0(1 review)
    1.9 mi

    Interlachen Avenue is a national historic district in Winter Park, Florida. Winter Park was…read morechartered in 1887. The city was founded as a wealthy winter resort for northern residents. The neighborhood includes homes, churches, and businesses constructed from 1882 through 1964. Architectural styles include Colonial, Mission, Monterrey, and Mediterranean Revival, This 5 acre, ten block neighborhood is bounded by Canton Avenue on the north, Knowles Avenue on the west, Lake Osceola on the east, and New England Avenue to the south. This neighborhood was added to the National Register of Historic Places on November 30, 2011. The oldest house in this neighborhood is at 231 North Interlachen Ave. It was built in 1882 as a vacation cottage for Francis B. Knowles, one of the the foundesr of Winter Park. When Interlachen became a historic district, two thirds of the property owners in the neighborhood had to agree to be historic. Once designated, all major repairs have to be approved by the Historic Preservation Board. Winter Park has one of the strictest requirements to become a historic neighborhood in Florida. Their rigid requirements means that there aren't many designated historic neighborhoods in the city even though there are many houses that could be considered historic. Visiting this neighborhood is special. There was a period in Winter Park's history when they let a lot of their historic buildings get torn down for development. It is nice to see that there is more care being taken now with the preservation of what is left. This is a wonderful neighborhood to walk around if you are in the area. They gorgeous older homes area what sets Winter Park aparrt from other cities in the atea and makees it such a desirable place to live.

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    Interlachen Avenue Historic District
    Interlachen Avenue Historic District
    Interlachen Avenue Historic District

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    Black Bear Trail - landmarks - Updated July 2026

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