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 […]

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+