Shopping & Dining in the Heart of Downtown Winter Park
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 […]
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 […]
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 […]
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. […]
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. […]
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 […]
Labor Day Block Party & Sidewalk Sales Live music with Joe R & the Icebox Sound Face painting & Balloon artists Bouncy House Sidewalk Sales
Winter Park Art Festival Amazing Art Handcrafted Goods 40+ Vendors Live Music
Winter Park Art Festival Amazing Art Handcrafted Goods 40+ Vendors Live Music
Trick or Treat Street, DJ and photo booth.
Grab your friends and come down to Cooper Creek Square for a special shopping experience. Enjoy promotions, giveaways and refreshments, then head over to Devil's Craft for Comedy Night. Free tickets for all who participate in Ladies Night.
Santa visits, Elf on the Shelf Scavenger Hunt and the lighting of the Christmas tree.