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 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 […]

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 captivating, high energy performance and a unique ability to connect with their audience, constructing an eventful and engaging atmosphere. Billy, and his wife Ellen, have […]

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 has also performed as a headliner in the Blues Alive Festival in the Czech Republic in 2019. You can find his album Mississippi Heat on […]

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 5-6:30pm| Featured Show Andrew Duhon 7-9pm Gary Key - Known as the “Walking Jukebox”, Gary has been performing for over 40 years covering classics like […]

Live music with Foggy Memory Boys Drawing from a deep well of musical experience the Boys have a unique perspective on string band music, contorting the sound into a New Mexican Wild-grass like nothing else out there… structured around strong lyrical content, powerful melodies, and a musical bond that only a band of true brothers […]