Winter Park Sidewalk Art Festival Prepares for 65th Show

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The groundhog may have seen its shadow weeks ago, but a local springtime tradition will return to Park Avenue on March 15, 16 and 17 with the 65th Annual Winter Park Sidewalk Art Festival.

The list of 219 participating artists was selected from more than 1,000 applications. Cash awards totaling $76,500 rank among the highest of any art festival in the country and include the Best of Show Purchase Award. The recipient becomes part of a special collection owned by the city.

“(The pieces) originally were all housed at the former library,” said City of Winter Park Communications Director Clarissa Howard of the collection, which is now managed by the city’s Public Art Advisory Board. “Due to the growing size of the collection and limited city-owned public spaces that are climate controlled, (the Advisory Board) is working to showcase the work in multiple locations.”

The Best of Show collection is currently housed at the Winter Park Library & Events Center campus, the J.K. and Sarah Galloway Foundation Community Gallery on the first floor of the Winter Park Welcome Center, and in the Chapman Room on the 2nd floor of Winter Park City Hall. The Public Art Advisory Board is also working on an online inventory to make the Best of Show collection and all other city-owned public art pieces accessible to a worldwide audience.

Irina Ashcraft’s artwork was chosen for this year’s festival poster. She was trained at the Latvian Academy of Art and relocated to Orlando in 1999. She has shown her work at several local and European galleries and festivals, and teaches art at Winter Park’s Trinity Preparatory School. Image courtesy of: Winter Park Sidewalk Art Festival

Behind the scenes

Winter Park Sidewalk Art Festival is more than an event, it’s a 501(c)(4) with an all-volunteer board that pools its resources to tackle a year-long logistical process. Priorities range from selecting judges and screening applications to arranging exhibit tent locations and scheduling live entertainment. But according to WPSAF Public Relations Manager Alice Moulton, refining the selection process was a key strategy in raising the festival’s profile.

“The number of artists has varied quite a bit over the years,” she said. “At one time there were about 600 artists; I think all you had to do at that time was apply and you were in.”

The number of participants may have been reduced from its early years, but the festival attracts an estimated 250,000 visitors to the downtown shopping and dining district. Photo by: Jim Carchidi

The application period begins in August and runs through mid-September with judges coming to town in late October to view submissions at Winter Park City Hall’s Commission Chambers. “We call it Screening Weekend,” Moulton said. Judges assign numeric scores to the works submitted with each application, but steps are taken to ensure a variety of fine art media – from jewelry to digital art – is represented. “It doesn’t just go by the highest (overall) scores, it’s the highest scores in each category.”

The show goes on

This year marks the return of a festival tradition: the Friday Night Concert. Beginning in 2022, the live music event was scheduled a week before festival set-up to offer adequate post-pandemic audience spacing. However, the move proved to be confusing and detracted from its impact as a festival kickoff event. “I think many people didn’t even realize we were putting on the concert during that time,” Moulton said. “People coming to town for the festival weren’t able to see the concert and the new schedule really didn’t represent its intent.”

The show will begin at 5:30 p.m. on March 15 with a celebration of the late Jimmy Buffett by tribute band, Gary Roland and The Landsharks. The vibe will take a jazzy turn at 7:30 p.m. when Michael Andrew and Swingerhead take the stage. Guests are invited to bring their own food and blankets, but are advised that no blankets larger than 10 feet are allowed and cannot be put down until 2 p.m. Additional live music performances will take place each day of the festival, the full schedule is available here.

Road closures and daily schedule

An estimated 250,000 visitors attend the three-day festival with many turning their attention to downtown’s retail and restaurant offerings. The following street closures are in effect during the event weekend:

  • Garfield Avenue
  • Lincoln and East Welbourne Avenues, from Center Street to Park Avenue
  • Morse Boulevard, from South Knowles to South New York Avenues
  • New England Avenue from West Park Avenue to Center Street
  • Park Avenue from West Canton to Lyman Avenues

Festival hours will be 9 a.m.-6 p.m. on March 15-16, and 9 a.m.-5 p.m. on March 17. Guests are advised that no pets, bicycles, motorized scooters or skateboards will be allowed inside the festival areas. For more information and to view a gallery of participating artists, visit

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