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