Cass Clayton Band is a 6-piece, female-fronted band that blends funk, soul, rock and contemporary influences. Cass and co-writer/producer, Taylor Scott, have been praised for their modern approach to songwriting, and they aim to continually innovate and provide unexpected twists for the audience. No two shows are ever the same, with the band effortlessly moving from […]

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 […]

The Wiedls w/ Candy Cigarette   Doors: 8pm Showtime: 8:30pm - 12am All-Ages Admission: $10 General admission only (reservations are not accepted) Food & Beverage: Kitchen serves the full menu until midnight. Bar closes at 1am. Outside food and drinks are not permitted.

The Leafy Greens Band Based out of Jupiter, FL, The Leafy Greens Band is currently on their summer tour, traveling 30,000 miles across America. This Folk/Americana acoustic duo showcases a […]

Zach Day Zach Day, born and raised in Mississippi, is a self-taught musician, singer, and songwriter. Zach has completed solo tours in Canada and across the U.S. multiple times and […]

Brought to you by Uptripping Local artists, live music, aerial performance and community gathering.

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. July 5 | Gary Key […]