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You are here: Home / Who’s Singing this week at Music on the Square?

Who’s Singing this week at Music on the Square?

June 28, 2022

TWO nights of Free Live Music in the Courtyard at Cooper Creek and its starts on Friday with Peggy Man, followed by our Saturday Show with Gary Key & Sam Osborne. Music on the Square has been Expanded to Fridays & Saturdays, 6-8pm for the 2022 Summer! Read below to learn about this weekend’s artists.

  • July 1st – Peggy Mann
    • 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. A Grand County gem indeed!   Listen in at www.peggymann.com
  • July 2nd – Gary Key & Sam Osborne
    • A staple in our local music scene, Sam & Gary have been playing music together for over two decades. They sing a wide selection of your favorite songs from Classic Rock to Country, Blues and more. Bring your dancing shoes and your song requests because they will know them all!   Listen in at www.garykeymusic.com

Check out the Full Summer lineup and learn more about each of the artists: HERE!

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.

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.

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