Cooper Creek Square

Music on the Square is a cherished summer concert series tradition in downtown Winter Park. Join us every Friday night, from 6pm-8pm, June 21-Aug. 30. Friday, June 21 Gabrielle Louise Boulder based singer-songwriter Gabrielle covers original Americana that, though rooted in Folk tradition, blends a sophisticated use of musical harmony with a lyrical love for […]

Help Stuff-a-Bus and donate unwrapped toys, clothes or gift cards to help make a difference just in time for the holidays.  All donations are going to the Shining Stars Foundation […]

Celebration of Lights Visit with Santa, enjoy holiday music and explore the Square with the Elf on the Shelf scavenger hunt.

Grab your friends and head to the stores at Cooper Creek Square for a fun evening of shopping.  Enjoy a variety of promotions, giveaways and refreshments.  Register for a $100 […]

Enjoy sidewalk sales, free face painting with Suzy-Q the Clown and live music with local favorite Andy Straus.

Peggy Mann Band Whatever style of music you enjoy, you’ll hear it along with many original songs found on one of seven albums. Winner of numerous vocalist and song writing awards, her band has been the winner of “The Best Band of Grand County” for six straight years. Music on the Square is a summer […]

High Country Hustle High Country Hustle brings big smiles and foot-stomping good times to venues and festivals across the United States. Formed in 2017, this four-piece bluegrass band delivers high-energy shows that are sure to get you moving. Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter […]

Oly   Singer-songwriter, Oly’s music blends traditional Rock, Folk, and Punk. He has played throughout the U.S. and has produced three full-length albums — the latest called “The Little Things That Come Between Us” was described as “a […]