Strangebyrds Let the holiday weekend begin with a captivating brew of talent, chemistry and harmony with Cari Minor & Ray Smith. Internationally recognized singer-songwriters and multi-instrumentalists that craft award-winning songs with a unique Folk/Rock Americana sound. Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy […]

Poudre Valley Playboys Their high-octane classic country-rockabilly-surf music gets any crowd jumping and hollering within the first few bars. With powerhouse bass licks and riveting electric guitar riffs, this duo sounds like a full band on fire. Enjoy music from a mix of genres from blues and Americana, to jazz and country in an intimate, […]

Leashy A Colorado super group channeling raw energy into razor sharp, hook-heavy indie rock. Alysia was recently voted by Colorado Sound listeners as the winner of the Outstanding Stage Presence […]

Gary Key & Sam Osborne As staple in our local music scene, Sam & Gary have been playing music together for over two decades. They sing a wide selection of […]

Andrew Duhon For over a decade New Orleans singer-songwriter Andrew Duhon has been performing on this stage. Every year he brings new songs full of deep and soulful stories. His latest album, The Parish Record, will keep you going back to long after the show is over. Music on the Square is a summer concert […]

The Leafy Greens Band Based out of Jupiter, FL, 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.  Enjoy music from a mix of genres from blues and Americana, to jazz and country in an intimate, outdoor setting surrounded […]