Music on the Square is a cherished summer concert series tradition in downtown Winter Park. Join us every Friday night, from 6pm-8pm, June 21-Aug. 30. Aug. 9 | Grant Sabin Trio Drawing from his Delta Blues influences, Sabin's unique musical style is characterized by biting slide guitar, a soulful growl, and heartfelt lyrics. His honest […]

Rose's Pawn Shop Rose’s Pawn Shop makes Americana-Folk-Rock music inflected with the pulsing, vibrant energy of their hometown Los Angeles. They weave old-time Appalachian folk, country, and bluegrass with poetic lyrics gleaned from hard lessons learned and years on the road. Rose's Pawn Shop has shared the stage with Lucinda Williams, Railroad Earth, and Jack White and The […]

The music continues with the Saturday Sessions from 4-6 PM. This series features a more laid-back setting, inviting you to relax by the fountain, enjoy a meal or a drink from one of the many Cooper Creek eateries, and immerse yourself in the sounds of up-and-coming artists as well as established performers.  It's the perfect […]

Huge in Germany Let's get nostalgic! Huge in Germany returns to Winter Park with big hair, big sound, and big hard rock vibes. Classic. Cover $18.50

Music on the Square is a cherished summer concert series tradition in downtown Winter Park. Join us every Friday night, from 6pm-8pm, June 21-Aug. 30. Aug. 16 | Last Call Romance Known for their modern take on a mid-century sound, along with original songs about love, heartache and everything in between. Last Call Romance delivers […]

The Patti Fiasco Jet-fueled by powerhouse front woman Alysia Kraft, The Patti Fiasco rides the edge of emotional extreme, delivering a brash yet fiercely soulful brand of rock and roll with a heavy dose of rockabilly, blues, and ballad. At times raw and volatile, and at others, sweet and lilting, the band fuses a hard-rock […]

The music continues with the Saturday Sessions from 4-6 PM. This series features a more laid-back setting, inviting you to relax by the fountain, enjoy a meal or a drink from one of the many Cooper Creek eateries, and immerse yourself in the sounds of up-and-coming artists as well as established performers.  It's the perfect […]