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 […]

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 […]

Stop Light Observations is an "anti-pop/not rock (but also isn't not rock) band born and raised in Charleston, SC." They're making their Devil's Craft debut July 6th at 9pm, and we are thrilled to introduce them to Winter Park on their Summer 2024 tour. Get yourself a preview at https://www.stoplightobservations.com/, and then catch them live right […]

Live Music with Stop Light Orchestra SLO is a 4-piece anti-pop/not rock (but also isn't not rock) band born and raised in Charleston, SC. 9pm | $10 | 21+

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 12 | Ethyl & the Regulars Denver's premier Honky-Tonk, Western Swing and Hillbilly Boogie Band; offering high-octane music that will bring you swinging onto the dance floor and grinning […]