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, […]

Mama Lenny & the Remedy Seven-piece powerhouse Mama Lenny and the Remedy deliver a high-energy fusion of soul, funk, rock, blues, and disco with hints of jazz, gospel, and Broadway. With infectious energy, the band delves into the joys and downfalls of love and life−always with a wink of humor and a witty turn of […]

Easy Tiger - 3-5pm An acoustic band with high energy and high heart, hailing from the wild jungles of Colorado.       Steve Postell - 6-8pm With a long career as a songwriter, producer and performer, Steve has played with artists including David Crosby, Jennifer Warnes, John Oats and Kenny Loggins.

Labor Day Block Party & Sidewalk Sales Live music with Joe R & the Icebox Sound Face painting & Balloon artists Bouncy House Sidewalk Sales