String Fling This four-piece acoustic string band brings a collective 200+ years of experience and a “we ain’t dead yet” attitude to bare on an extensive blend of Americana, Classic Folk, and Country to contemporary music. Originals and classics alike will quench your thirsty ears! Music on the Square is a summer concert series tradition […]

Denver DJ Bassotron Denver DJ BASSOTRON returns to Winter Park to bring us another epic dance party at Devil's Craft. FREE Friday fun! 9pm-midnight Ages 21+ IDs are required at the door. No outside food or beverages.  

Peggy Mann Band Whatever style of music you enjoy, you’ll hear it at Peggy Mann’s shows along with many original songs found on one of seven albums. Mann is the winner of numerous vocalist and song writing awards and her band has been the winner of “The Best Band of Grand County” for six straight years. […]

LowDown Brass Band The LowDown Brass Band is a uniquely strong representation of Chicago Music culture. Providing a modern take on soul, funk, hip hop, and jazz, this multifaceted all-horn band boasts freedom through the art of their craft, whilst gaining critical acclaim from The Gazette, Fame Magazine, The Chicago Reader and more. LowDown maintains […]

Blood Sugar This mother and daughter duo can bring down the house with a mix of Americana, Folk, and Blues; delivering rich vocals and mesmerizing and harmonies that could only come from shared DNA. Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from […]

Justin Roth Justin Roth is a nationally touring singer/songwriter/acoustic guitarist based in Colorado. His brilliantly inventive fingerstyle guitar arrangements define his unique mix of indie folk and instrumental guitar music. Enjoy music from a mix of genres from blues and Americana, to jazz and country in an intimate, outdoor setting surrounded by beautiful flower gardens, […]