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Discover Park Avenue

Autumn Art Festival FAQ

Back to Blog The Winter Park Autumn Art Festival is one of Central Florida’s most beloved cultural events, and for good reason. Every October, locals and visitors alike gather at Central Park to celebrate Florida artists, shop for original artwork, enjoy live music and take in the charm of Park Avenue. Whether you’re attending for…

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Arts & Entertainment in Winter Park

Back to Blog Winter Park, Florida and the surrounding Central Florida area is bursting with creativity and culture. Whether you’re into art, music, theater or just looking for something fun and inspiring to do, this charming city has something for everyone. Check out these amazing spots that help make Winter Park such a vibrant and…

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Best Hotels Near Winter Park Florida

Back to Blog Winter Park is one of Central Florida’s most charming destinations-brimming with art, culture, boutique shopping, and incredible dining. Whether you’re visiting Rollins College, coming for the annual Autumn Art Festival or taking a stroll down Park Avenue, you’ll want the perfect place to stay. Here’s your guide to top hotels in Winter…

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Michelin Stars & More Award-Winning Dining in Winter Park

Back to Blog A Culinary Tour of Winter Park’s Award-Winning Restaurants Winter Park, Florida, is more than just a charming town with cobblestone streets and upscale boutiques-it’s also home to some of Central Florida’s most celebrated dining experiences. From Michelin-starred elegance to local magazine favorites, these standout restaurants have earned critical acclaim and the loyalty…

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Winter Park Shopping Districts

Back to Blog Winter Park is a gem of a town that blends upscale shopping with small-town charm. From its brick-lined streets and boutique-lined avenues to its vibrant dining scene, this stylish destination invites you to shop, stroll and savor. Whether you’re planning a day trip or a weekend escape, here’s your guide to discovering…

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Tours to Take in Winter Park

Back to Blog Nestled just outside of Orlando, Winter Park is a charming city brimming with natural beauty, culture, and hidden gems waiting to be explored. Whether you’re a local looking to rediscover your backyard or a visitor searching for an authentic Central Florida experience, these standout tours offer a unique look at what makes…

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10 Restaurants to Visit in Winter Park

Back to Blog Winter Park, Florida, is a vibrant city known for its rich history, beautiful parks, and thriving food scene. Whether you’re a local or just visiting, you’ll find an impressive array of restaurants that cater to every craving. From farm-to-table American cuisine to Mediterranean, Japanese, and Italian delights, Winter Park has something for…

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Michelin-Star Soseki Omakase Leads Winter Park’s Fine Dining Scene

Back to Blog In 2022, Winter Park native and culinary visionary Michael Collantes achieved a historic milestone by earning the city’s first Michelin Guide star for his intimate 10-seat restaurant, Soseki Omakase. This accolade not only elevated Winter Park’s dining scene but also underscored Collantes’s dedication to culinary excellence.​ Reflecting on the significance of the…

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10 Most Instagrammable Places in Winter Park

Back to Blog Winter Park attracts thousands of people each year with its fine dining, boutiques, and sunny weather, making it the perfect destination for Instagram photos. Whether you’re exploring downtown Winter Park, enjoying a meal at one of the many Winter Park restaurants, or attending the Winter Park Art Festival, there’s no shortage of…

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25 Things to Do in Winter Park

Back to Blog Park Avenue and the surrounding Winter Park community offer residents and visitors a variety of activities. Here are 25 Things to Do in Winter Park – from enjoying one of our local parks and exploring a museum, to dining al fresco and attempting to paddle board, the Winter Park, Florida area is…

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Park Avenue

History

 

1881: New Englanders Oliver Chapman and his friend Loring A. Chase purchase 600 acres bordering Lakes Maitland, Osceola, Virginia and Killarney for $13,000. They refer to their property as a “necklace” of lakes surrounding lush acreage. Their goal is to develop a residential community of winter homes for wealthy Northerners — a “planned community.” It is the very first one in Florida, and they name the new town Winter Park. Designing around a central park and its main street, Park Avenue, they designate home sites, a hotel, churches, schools and parks. The duo market their Florida enclave to northerners fleeing harsh winters. Soon the railroad pulls into Central Park with loads of affluent tourists who stroll down Park Avenue.