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Music on the Square – Expanded!

May 25, 2022

Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. 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, a bubbling fountain, and fresh mountain air. Musicians and audiences from across the country are drawn to this sweet summer music series that is sure to delight the senses.

We are excited to announce another summer of amazing music both Fridays and Saturdays from 6-8pm.  Check out the lineup below and click HERE to learn more about each of the artists!

  • June 24 – Sarah Morris
  • June 25 – The Blue Shoes
  • July 1 – Peggy Mann
  • July 2 – Gary Key & Sam Osbourne
  • July 8 – Strangebyrds
  • July 9 – Kory Montgomery
  • July 15 – Johnny O Band
  • July 16 – Andrew Duhon Trio
  • July 22 – Family Recipe
  • July 23 – Carter Sampson
  • July 29 – Delta Sonics
  • July 30 – Chris Smither
  • Aug. 5 – Cowboy Dave
  • Aug. 6 – Brad Fitch & Mark Rashid
  • Aug. 12 – Forest Sun
  • Aug. 13 – Taylor Shae Band
  • Aug. 19 – Rob Drabkin
  • Aug. 20 – Hunker Down
  • Aug. 26 – Tight Like That
  • Aug. 27 – Joe R & the Icebox Sound
  • Sept. 2 – Blood Sugar
  • Sept. 3 – Moffat Tunnel Band

Shows will go on rain or shine – we are hardy here at 9,000 feet unless it is a massive downpour and the venue cancels due to safety concerns. This series is free and everyone is welcome.

Cooper Creek Square is a designated Entertainment District which allows guests to purchase alcoholic beverages from any of our restaurants during the show and enjoy them in the courtyard or while wandering through the shops.  

We have a ton of fun events coming up this Summer at Cooper Creek Square!  Join us for one of them, or just to enjoy the Courtyard Lights and dinner at one of our Restaurant Row dining options! Sign up for the Cooper Creek Square email newsletter and follow along with our social media channels to stay up-to-date on current happenings at Cooper Creek Square! Instagram | Facebook

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  • Dine
  • Shop
  • Experience
  • Music on the Square
  • Services
  • Events & Buzz
  • Contact Us