MARCH 18-20, 2022

Music & Entertainment

No Friday Night Concert at The 2021 Winter Park Sidewalk Art Festival


Traditionally the Friday night concert at the festival is a highly-anticipated springtime event in Central Florida, attracting enthusiastic attendees from around the state and beyond. Locals show up at daybreak on Friday morning to claim a space to spread out their blankets and set up their lawn chairs in front of stage in north Central Park. More than just a concert, the event takes on the feeling of a neighborhood party with elaborate spreads of food and drink.  

Due to COVID-19 and concerns about social distancing the 62nd festival will not have a Friday night concert and will have scaled back activity on the stage throughout the festival. The concert, which generally focused on Jazz artists, gained statewide notoriety in the 80’s and 90’s when such greats as Herbie Mann, Dave Brubeck, Al Hirt, Ramsey Lewis, The Rippington’s, Grover Washington, Jr., Bob James, Earl Klugh and Warren Hill were among the headliners.  During that time period, the local Jazz station, WLOQ partnered with the festival to bring these big-name artists to Winter Park.  WLOQ went off the air in 2012 and funding for the concerts decreased without their industry connections and advertising support. But the excitement continued. The festival took over the booking of talent and sponsorships with the help of board member Wayne Osley of Oz Media, who continued to secure outstanding, crowd pleasing headliners. Besides the main concert, the whole weekend is filled with popular local groups and talented young entertainers on the main stage, along with appearances by some of central Florida’s finest orchestras and ensemble groups.  


We look forward to you joining us again in 2022 when the tradition of great Friday night concerts and a weekend full of wonderful music and entertainment returns.


2021 Winter Park Sidewalk Art Festival Talent Lineup Information Coming Soon!

Friday May 14, 2021  
   3:00 - 4:00 pm Big Tiki and The Mai Tai’s
   4:30 - 6:00 pm Brazillian Jazz
Saturday May 15, 2021  
   10:30 - 11:30 am Paint it Black (Contemporary Classical)
   1:00 - 2:00 pm Josh and Company
   3:00 - 4:30 pm Mike Petrovich
   5:00 - 6:00 pm Dream Catcher
Sunday May 16, 2021  
   10:30 - 12:00 pm Joshua Grimes
   1:00 - 1:30 pm Orlando Children's Choir
   2:00 - 3:00 pm Cat Ridgeway
   3:30 - 4:45 pm Dayve Stewart BAnd