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 […]

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 […]

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 […]

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+

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 […]

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 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 […]

Caitlin Krisko and The Broadcast is a psychedelic soul rock band hailing from Asheville, North Carolina. Caitlin is known for her powerhouse vocal performances and is backed by incredible musicians. Together […]

Casa Mexico 11th Anniversary Celebration  

Mighty Mystic Get tickets here. Mighty Mystic is a leader in the U.S. Reggae scene and labeled by many as one of the more prolific artists to develop outside of […]

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 19 | Delta Sonics […]

DJ Al Your Pal 9pm | Cover Charge

Join us for our first annual Farmers Market from 4-6pm.  Peruse an intimate selection of vendors including fresh bread, cookies, meat & cheese, and jerky while enjoying live music, aerial […]

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 […]

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 26 | The Two […]

Rooted in reggae, infused with jamtronica, and charged by drum and bass, this 4-piece pushes dancefloor vibes directly into the future.  Giant Walking Robots present a sound both familiar and […]

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 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 […]

Barre Chord Bangers The Barre Chord Bangers are a Denver-based cover band focused on pop and punk songs spanning several decades. Songs range from the early days of punk (Ramones, […]