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Winter Park, Florida – Park Avenue

Main Streets 2017 – Florida

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It sits just north of Orlando, but you won’t find theme parks in Winter Park. Instead, at the heart of this appealing community, you’ll find Park Avenue, a handsomely tree-shaded, brick-paved destination for shopping, dining both indoors and on the sidewalk, and a vibrant art and cultural scene.

Founded as a winter resort around the turn of the 20th century, Winter Park today is rich with green space. It has some 70 parks, where you can enjoy special events, festivals and celebrations throughout the year, or just sit in the shade to enjoy a Central Florida afternoon. Central Park, the city’s largest, faces along Park Avenue, just down the street from the Charles Hosmer Morse Museum of American Art.

The Morse Museum at 445 North Park is home to the world’s fullest collection of works by legendary glass artist Louis Comfort Tiffany. Along with his famed leaded-glass lamps and windows, you can see Tiffany-created jewelry, art glass, and even the chapel interior he created for the the 1893 World’s Columbian Exposition in Chicago. The museum also has late 19th- and early 20th-century American painting, pottery and decorative art.

Up and down Park Avenue are more than 140 boutiques, cafes, upcale restaurants and art galleries. The street also hosts two highly regarded art festivals. The Autumn Art Festival is the only juried fine art gathering that exclusively showcases the work of Florida artists; each year, 180 artists are chosen to show their works in mid-October along Park Avenue and in Central Park.

In March, the Winter Park Sidewalk Art Festival draws over 350,000 visitors to see highly creative work from some 225 sidewalk artists. Organized entirely by local volunteers, the festival has been named several times as one of the nation’s top art fairs and fine art shows.

Park Avenue is also home to the Casa Feliz Historic House Museum, a fine restored Spanish-style home where a different music group performs in the main parlor each week. Also contributing to Winter Park’s rich cultural life are the The Annie Russell Theatre, Florida’s longest continuously operating theater, and The Zora Neale Hurston National Museum of Fine Arts. Just below the southern end of Park Avenue, the campus of Rollins College has been ranked as one of the most beautiful U.S. colleges by the Princeton Review.

All photos courtesy of the City of Winter Park Communications Department

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Sarasota, Florida – Main Street

Main Streets 2016: Florida

Along one of America’s most appealing urban waterfronts, Sarasota’s Main Street leads from a scenic marina into a lively downtown that offers great shopping, arts and music — and one of America’s most unique and colorful festivals.

October’s annual Sarasota Chalk Festival celebrates Italian street painting, a form of art that’s both visual and theatrical, as artists use chalk and other materials to create works of art, often on a very impressive scale, while visitors look on. The festival has been recommended by the New York Times’s “Guide to Intelligent Travel,” and there’s nothing else quite like it in the United States. Each year’s festival has a theme, and pavement artists come from around the world to participate. The festival has historically been held on Burns Square, near Main Street, but in 2013 its growth and popularity has led to its extension up Pineapple Street, across Main Street in the heart of downtown.

At night, Sarasota comes to life on Main Street and its surrounding area, with nightclubs, coffee bars, restaurants that feature live music, professional and community theater, and bars that offer karaoke and trivia contests. At Main Plaza at the north end of Main, the Regal Hollywood 20 movie theater has a distinctive art-deco facade that recalls Sarasota’s first heyday in the 1920s, when John and Charles Ringling of the famed circus family helped to lead the city’s development. The Ringlings brought a passion for art and architecture that’s still visible in the downtown’s many buildings of Italian design. McCurdy’s Comedy Theatre and Humor Institute, just a block from Main on Ringling Boulevard, hosts world-class comedy acts.

No mention of Sarasota’s Main Street would be complete without the waterfront. Main Street leads right onto Marina Plaza, which ends at Marina Jack, a popular seafood eatery whose views of Sarasota Bay are hard to beat. The Marina Jack Trail leads walkers along the waterfront and around nearby Island Park. In this peaceful green retreat, kids can splash around in the Steigerwaldt-Jockey Children’s Fountain, and you can look out across the water as the brilliant sunset illuminates this laid-back, friendly city.

Chalk Fest Photo courtesy of Chalk Fest
Bayfront Park photo courtesy of James Sweiderk

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