Destination: Winter Park, Florida

Destination: Winter Park, Florida

The 56th Winter Park Sidewalk Festival will be held March 20th through the 22nd in Winter Park, Florida. It is one of the nation’s oldest, largest, and most prestigious juried outdoor art festivals.

The show is currently ranked #1 on’s list of America’s Best Art Fairs, and is ranked #1 in the South and #5 in the Nation by Sunshine Artist Magazine, based on reported sales by the artists. Hosting more than 350,000 art-loving enthusiasts each year, over 1,100 artists from around the world apply to be one of the 225 judge-selected featured artists. Artists compete for 63 awards totaling over $72,500 in prize money.

The festival hosts a wide variety of outstanding artwork including clay, drawing and pastels, glass, digital art, fiber, glass, jewelry, leather, mixed media, photography, painting, printmaking, sculpture, watercolor, and wood. The festival also bolsters a love of art for young children by offering daily children’s workshops for all ages.

Winter Park was founded in the late 1800s, and the town is heavily influenced by Spanish Mediterranean architecture. One of the city’s defining architects was James Gable Rogers II, who designed the city’s Grenada Court shopping area, the Olin Library, the Holt and Mizener homes, and the Florida State Supreme Court Building in Tallahassee. Roger's home in the heart of Winter Park, named “Casa Feliz,” (seen right) now serves as a museum that overlooks the golf course.

Just a ten minute drive from Orlando, Winter Park is a shopping and arts hub. The town’s central brick laden artery, called “Park Avenue,” originates at the town’s historic school, Rollins College, and winds about a mile through a thriving commercial district. Park Avenue is lined with scenic live oaks draped in moss, and takes travelers by clothing boutiques, art galleries, sidewalk cafés, and restaurants.

Winter Park is also home to three notable museums, all of which are within walking distance of each other.

The Charles Hosmer Morse Museum of American Art holds the world’s most comprehensive works of Louis Comfort Tiffany, including jewelry, pottery, paintings, art glass, lamps, and windows. Upcoming exhibitions include, “The Bride Elect” which will showcase over 250 wedding gifts from Elizabeth Owens Morse, a socially prominent Chicago bride married in 1905. “Selection” includes works from the Harry C. Sigman Collection of European and American Decorative Art, with works from the late 19th and early 20th century.

The Cornell Fine Arts Museum is set on the Rollins College campus and overlooks Lake Virginia. The museum is home to the oldest collections in the state, with more than 5,000 objects on exhibit, ranging from antique to contemporary. Upcoming exhibitions include “Kara Walker: Harper’s Pictorial History of the Civil War” reflecting an illustrated compilation of news reports about the Civil War (first published in 1866), as well as “Tobi Kahn: Reverie” reflecting back on 30 years of works in various media.

The Polasek Museum offers over 200 works by Czech-born American sculpturer, Albin Polasek. The museum is the previous retirement home of the artist, and is listed on the “National Register of Historic Places.” It is one of only 30 members of the “National Trust’s Historic Artists’ Homes and Studios.” In addition to the home, the museum features a chapel and a captivating garden which includes over 50 outdoor sculptures and dates back to 1949.

While you’re there, stay at The Alfond Inn (the Rollins College boutique hotel), or the Park Plaza Hotel. Before leaving the area, you can relax and take in a film at the Enzian outdoor theater, just a few minutes from Park Avenue. The venue is amidst 400-year-old oak trees, and offers audience members lounge chairs, as well as the option to dine on first-rate food, craft beers, wine, and cocktails.

For more information, visit:

Winter Park Sidewalk Art Festival at

Note: This article is displaying as it appeared in Volume 18 of our PlaneSense: Informational Quarterly newsletter.
Photo courtesy of Chip Weston, Alice Moulton

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