Cooper Creek Square

Shopping & Dining in the Heart of Downtown Winter Park

  • Dine
  • Shop
  • Experience
  • Music
  • Services
  • Events & Buzz
  • Contact Us
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

Recent Blog Posts

Summer Send-Off

As the golden days of Summer begin to wane, we invite you to celebrate the season’s end with a series of spectacular events at Cooper Creek Square. There’s something for everyone, so gather your friends, family, and neighbors, and let’s make these final Summer moments unforgettable! Final Live Music Shows Carter Sampson The heart and soul of our Summer have been the incredible music events we’ve hosted, and we’re going out with a bang! Don’t …

Celebrate Independence Day Weekend at Cooper Creek Square!

Are you ready for a spectacular 4th of July weekend filled with music, entertainment, and community spirit? Look no further than Cooper Creek Square! We have an exciting lineup of events planned to make your holiday weekend unforgettable. Whether you’re a local resident or a visitor, there’s something for everyone to enjoy! Wednesday, July 3rd: Kickoff Celebration Live Music in the Courtyard Start your festivities on Wednesday, July 3rd with an uplifting musical performance by Leafy Greens from 4:00 PM to 6:00 …

Your Culinary Adventures Awaits…

Nestled in the heart of Winter Park’s vibrant downtown lies a hidden gem for all food lovers and night owls – Cooper Creek Square’s Restaurant Row. With its eclectic mix of nine restaurants, this culinary hotspot has become the go-to destination for those looking to tantalize their taste buds with flavors from around the globe. From casual bites to upscale dining experiences, Restaurant Row offers a diverse range of options that cater to every palate …

Discover the Heart of Cooper Creek Square: Sign Up for Our Newsletter!

Are you ready to stay in the loop with all the exciting happenings at Cooper Creek Square? Whether you’re a local resident or a frequent visitor, our email newsletter is your ticket to the latest events, musical performances, and exclusive offers from your favorite shops and restaurants. By signing up, you’ll never miss a beat of what makes Cooper Creek Square a vibrant and dynamic community hub. Imagine strolling through the Square, knowing exactly when …

Summer Music Line-Up Announced

We are thrilled to reveal the lineup for our 2024 Summer Music Series! Music on the Square, a cherished summer concert series tradition, takes place on Fridays, 6-8pm at Cooper Creek Square in downtown Winter Park. This year, we are introducing Cooper Creek Square Saturday Sessions- live music every Saturday, 4-6pm. Cooper Creek Square, a designated Entertainment District, permits guests to buy alcoholic beverages from any of our restaurants during the event and savor them in …

Join our Email List

Stay in the loop with all the exciting happenings at Cooper Creek Square. Sign Up for our Email Newsletter

  • Home
  • Leasing
  • Sitemap
  • Directory

Copyright © 2025 Cooper Creek Square.

Free Covered Parking.

  • Dine
  • Shop
  • Experience
  • Music
  • Services
  • Events & Buzz
  • Contact Us