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    Winter Garden Historic District

    4.9 (15 reviews)

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    Ariel W.

    Winter Garden was settled in the 1850s and the town was established in 1908. Like many Florida towns, it grew when the railroad arrived in the 1880s. The early town consisted of scattered farms and homesteads along the south shore of Lake Apopka. The economy was based on the citrus and vegetables the farmers grew. At the turn of the century a small commercial district emerged along Plant Street and from that residential neighborhoods began to appear. The historic district is made up of 26 buildings from 1890 through 1945 with most building dating between 1915 and 1940. The entire historic district is 100 acres bounded by Woodland, Tremaine, Henderson, and Lake View Streets. This district was added to the U. S. National Register of Historic Places on August 1, 1996. The historic district has maintained its Old Florida charm while providing today's visitors with a number of shops, museums, art galleries, breweries, and restaurants to visit. In the center of the historic district is Centennial Plaza where there is a fountain with swings around it. The clock tower is also another landmark in the downtown area. On Sundays there is a farmers market. During my visit the downtown was beautifully decorated for the holidays. A large tree was set up and the whole downtown was covered in lights. Several areas were set up so you could take pictures. I even spotted Santa. My time in this lovely town was short but I saw enough to make me want to come back soon.

    Rachel M.

    I sure love the Winter Garden Historic District. Seriously, if I can live in a community that is walkable to cafes, Bikeable with a nice bike/walk path, an awesome family oriented bustling farmers market and more, I would. I just explained Winter Garden right here! This is it. It's super close to Orlando and it's just the cutest town. They also have a near by mini food hall called Plant Street Market and tons of the cutest local boutiques of all types of items and restaurants. It's super ideal. Definitely check it out! I do love the area!

    Andres A.

    I love Winter Garden. Everything is so clean and beautifully landscaped. Walking in their downtown area is great. They have plenty of small shops and restaurants to enjoy yourself. Every time I visit my parents in Florida we make a point to stop and visit. As you walk on their center median, it feels like a sanctuary there with the water fountain, benches and tables to dine at. Everything is so nicely decorated, I remember visiting one year during Christmas time and the decorations were excellent. Kudos to the City Leaders, their efforts make this place a gem.

    The entrance to the town. Surrounded by white roses.
    Tensy M.

    The name is very appropriate, this town is like a giant garden. Flowers everywhere, roses, amaryllis, and others. (See pic) Many little coffee shops along main street and other boutiques. Even the parking garage is pretty here (see photo) There is a lake that you can reach through the little streets. Great for a picnic. Locals go to a market place at the end of main street where they brew their own beer and have other original interesting booths of food.

    The Clock
    Maria A.

    Having recently moved to Orlando, we make it a habit to explore a new city or town in the area. This time we went to Winter Garden Historic District. Many places to dine and shop. Super cute atmosphere. Definitely make your way there.

    Craig L.

    Not sure what happened. The Farmers Market did not come up in my search. Oh well. That's where I am. Used to be a regular until I changed my work schedule. Now I usually work on Saturday and miss out in this award winning weekend experience. Love coming here. Spacious. Pleasant. Live music. Food vendors. Every kind of craft and goodie you can imagine!

    Laura G.

    Winter Garden Historic District is lovely. It has beautifully restored buildings that add character and charm to Main St. In 1996 Downtown Winter Garden was listed on the National Register of Historic Places. The old movie theater was restored and the Edgewater Hotel was saved from being knocked down. Several years ago a Clock Tower that chimes was added along with many other beautification projects. Several times a year the mornings are filled with the laughter and chatter of younger children on school field trips. They visit the Heritage Museum and take photos on the old railroad car. A parking garage was added behind the scenes when street parking became limited. The city added a large covered pavilion that hosts the farmers market and monthly car shows. It can also be booked as a venue. Winter Garden has become the new charming place to dine, shop, socialize and explore.

    Cynthia R.

    Since we went to this place we returned the next day. We found the place the atmosphere. The store, the water jets for the children. The museum. Everything very nice organized, clean. Hoping to return in December to see the decorations. The public bathroom is very clean.

    Jessie L.

    I am completely in love with Winter Garden's historic district. Plant Street may be small but it packs so much charm. There are several options if you're looking for a place to eat and Axum offers my personal favorite cup of coffee. Is it a beautiful day outside? Have it al fresco! There are plenty of places with outdoor seating, so enjoy the scenery! Maybe you're craving a drink? Crooked Can Brewery, nestled within Plant Street Market, is the place to go. The Edgewater Hotel, Garden Theater, Railroad Museum and the overall architecture give so much to Plant Street's nostalgia and really make the area someplace unique and special. I really am in love with this little place. I find myself up here pretty much any day I have off. It just gives off such a good vibe and holds a special place in my heart. If you come out here, there is no way you'll be disappointed.

    T-shirt from Heritage Museum
    Nick S.

    Terrific place to walk, shop, eat, relax, wander, have dessert, see Jazz or a show They've really made this brick street area something special. There's a nature park nearby (free) and parks on a big lake. The Orange Blossom Rail to Trail runs throigh town. There are a couple museum / heritage exhibition space where the railroad station was. There's a marketplace with gourmet food vendors and a craft brewery. It's all very nice.

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    Review Highlights - Winter Garden Historic District

    . There is a railway museums and a heritage exhibition space right on Plant Street

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    Berlin Wall Segment - Thickness of the Berlin Wall

    Berlin Wall Segment

    4.2(6 reviews)
    15.5 kmDr. Phillips, Horizons West / West Orlando

    Not many people are aware that a segment of the Berlin Wall stands behind The Hard Rock Cafe at…read moreUniversal Studios Orlando CityWalk. I passed by it dozens of times for nearly two years and never gave it even so much as a glance. Then one day someone told me it was there. And what do you know? it is! It's amazing how blind we can be sometimes to things that are right in front of us! I think it is amazingly awesome that we are lucky enough to have such a rich piece of history in Orlando. And it's not roped up in some museum with signs posted everywhere warning "Do Not Touch." Nope, it's right there all out in the open. Go ahead and put your hands right on it. It's amazing, just amazing, I tell ya! DO NOT go to Universal Studios and not take the time to walk behind The Hard Rock Cafe and see this piece of history!

    So many of the Berlin Wall segments sit outside in California, but this is the only one permanently…read moreplaced in Florida. This stands in a very odd place, basically if you are walking towards Hard Rock Café and coming from the backend where the University Studio's Globe is, the Wall is on the right side of the Hard Rock Café building. One would never even know it is there, as everyone goes inside Hard Rock Café from the other entrance. While observing the wall, I seen countless people just walking around and no one even seems to notice this significant piece of history right in front of them, how sad? If you are in Orlando and visit the CityWalk, definitely checkout the Berlin Wall Segment. [Review #374] (20th Review of 2016)

    Photos
    Berlin Wall Segment - Thickness

    Thickness

    Berlin Wall Segment - Behind hard rock

    Behind hard rock

    Berlin Wall Segment

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    Citrus Tower - Orange Butter Cream drink!!!

    Citrus Tower

    3.9(56 reviews)
    15.3 km

    The Citrus Tower in Clermont is one of those classic Florida roadside landmarks that still feels…read morerooted in the state's older tourism era. I've been to the Lake Placid tower, which is closed, so it was nice to see this one still operating. I passed through at 6am, well before sunrise, so the doors weren't open yet, but even from the outside the orange and white stripes and the height of the structure make it stand out. Built in 1956 as a 226 foot observation tower meant to showcase the miles of surrounding orange groves, it once drew up to 500,000 visitors a year when US 27 was the main north south route through Central Florida. Today the groves are mostly gone, but the tower remains open as a nostalgic attraction. Admission is usually around the ten dollar range for adults, depending on the season, and gets you access to the elevator ride up to the 360 degree observation deck. Considering the history behind it, including five million pounds of concrete, 149,000 pounds of steel, and a grand opening that drew representatives from Cypress Gardens and Silver Springs back in 1956, it's an inexpensive way to experience a piece of old Florida. Next time I'm passing through during actual business hours, I'll make a point to go up. [Review 1620 of 2025 - 2197 in Florida - 25168 overall]

    Wow, Florida is flat! :-D…read more I added the Citrus Tower onto my "to see" list when I found out I was going to be in Clermont. You don't need a whole lot of time here, but really appreciate how authentic they've kept the Tower. Instead of modern signage at the top, they still have hand-painted directional signs. I loved that! I also appreciated how they have ample labeling that tells you what you're looking at. They should rent binoculars; it could help them get toward their fundraising goal to support the Tower. I would have paid to rent some (e.g. they could hold your ID whilst you use them). The little cafe downstairs was pretty good, too; I grabbed a tea from there. Nice way to spend a bit of time! 2025: 13/100

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    Citrus Tower
    Citrus Tower
    Citrus Tower

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    Clermont Historic Village Museum

    Clermont Historic Village Museum

    4.3(7 reviews)
    18.1 km

    We came to visit this little historic village and it's very scenic. The trees are so pretty too…read more There is parking and public restrooms available. We made a bad choice for dinner but I will return.

    The Clermont Historic Village is a collection of historic buildings in Clermont, Florida. The City…read moreof Clermont purchased the land for the village in 1996 and it included the Train Depot and the Quonset Hut. Through the years various other historic buildings were moved to the village. The non profit South Lake Historical Society, formed in 1997 operates the village in conjunction with the City of Clermont. The mission of the historical society is to preserve, maintain, and share the history of South Lake County's pioneer families. The village opened in 2005. The historical society gives tours which covers the period of history from the 1800's to WWII. There are seven buildings that make up the village. These include the Herring Hooks Schoolhouse which was the last building added to the property. It is a replica of an 1881 one room schoolhouse that used to exist near Jack's Lake and served as Clermont's first school. It was recreated using old photographs. The Cooper Memorial Library was built in 1914 and nicknamed The Little Cooper. It was moved to the village from West DeSoto Street in 2009. The outhouse is a replica of one and was built as an Eagle Scout project. The Train Depot stands in its original location. It received refurbishment in 2011. The Quonset Hut was built by the US military and it is original to the WWII era. It has been turned into a museum. The Kern House was built in 1895 on Montrose Street in a traditional New England style by Alexander Kern. He was one of the original signers on the incorporation of Clermont. The house was moved to the village in 2008. The Townsend House was built in 1895 on SR 50 by the first Black family to move to Clermont, James and Sallie Townsend. It was the first building to be moved to the village in 2002 and it opened for tours in 2005. The Historic Village is free but asks for a suggested $5 per person donation. It is open for tours Saturday and Sunday between 1 and 4. You can contact them for private tours and rentals. Every year the Historical Society hosts a Heritage Day Festival. During my visit there was a very nice Christmas village on display. I love how the city of Clermont has preserved their history in these buildings. This is a great place to get a glimpse of what life was like at the turn of the century through WWII.

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    Clermont Historic Village Museum - Old train station?

    Old train station?

    Clermont Historic Village Museum - WW II Museum

    WW II Museum

    Clermont Historic Village Museum

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    Winter Garden Historic District - landmarks - Updated June 2026

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