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Music on the Square

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. 

The 2020 series will run every Friday from 6-8 pm, June 19 through Sept. 4.  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. Some tables and chairs are available, as well as camp chairs around the fountain and courtyard. 

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

 

 

 

 

 

 

Recent Blog Posts

Cooper Creek Square Events: Aug. 15-31

Live Music and Great Food Specials are happening Every. Single. Week. At Cooper Creek Square this Summer! Take a look at the event lineup for the next couple weeks and find our Restaurant Row highlights below! August 15, 5-7pm: Live Music & Pizza Night at Big Trout Brewing CompanyEnjoy Live Music by Burnt Orange along with 1/2 price Pizza & Beer August 17, 9pm: Latin Night with DJ Mr. Groove at Devil’s CraftNew drink specials each week!  Admission $5  *Every Wednesday All …

Cooper Creek Square Events: Aug. 1-14

Summer Events are Happening at The Square! Will You Be There? Live Music and Great Food Specials are happening Every. Single. Week. At Cooper Creek Square this Summer! Take a look at the event lineup for the next couple weeks and find our Restaurant Row highlights below! August 1, 5-7pm: Live Music & Pizza Night at Big Trout Brewing CompanyEnjoy Live Music by Burnt Orange along with 1/2 price Pizza & Beer August 3, 9pm: Latin Night with DJ Mr. Groove at Devil’s …

Cooper Creek Square Events: July 6-17

Summer Events are Happening at The Square! Will you be there? Live Music and Great Food Specials are happening Every. Single. Week. At Cooper Creek Square this Summer! Take a look at the event lineup for the next couple weeks and find our Restaurant Row highlights below! July 8, 6-8pm:  Music on The Square with StrangebyrdsCari Minor and Ray Smith are award-winning singer-songwriters and multi instrumentalists, crafting songs with a unique Americana sound they call “Blue Collar …

Cooper Creek Square Events: July 18-31

Summer Events are Happening at The Square! Will you be there? Live Music and Great Food Specials are happening Every. Single. Week. At Cooper Creek Square this Summer! Take a look at the event lineup for the next couple weeks and find our Restaurant Row highlights below! July 18, 5-7pm: Live Music & Pizza Night at Big Trout Brewing CompanyEnjoy Live Music by Burnt Orange along with 1/2 price Pizza & Beer July 20, 9pm: Latin Night …

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

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 MannWhatever style of music you enjoy, you’ll hear it at Peggy Mann’s shows along with many original songs …

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