Shopping & Dining in the Heart of Downtown Winter Park
Blood Sugar Blood Sugar is a mother and daughter combo with a multi-talented band (each member a unique artist on their own) that bring a mix of Americana, Folk, and Blues; delivering rich, mesmerizing vocals and harmonies that could only be derived from shared DNA. Music on the Square is a summer concert series tradition […]
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 […]
First Friday brought to you by Uptripping. Local artists. Live music.
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 […]
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 […]
Enjoy sidewalk sales, free face painting with Suzy-Q the Clown and live music with local favorite Andy Straus.
Winter Park Art Festival The Winter Park Art Festival is an annual juried art and craft show featuring an amazing array of original artwork and handcrafted goods. This free two-day event will be showcasing local and national artists representing a variety of mediums including paintings, sculptures, photography, ceramics, glass, wood, and more. While browsing the artist booth […]
Winter Park Art Festival The Winter Park Art Festival is an annual juried art and craft show featuring an amazing array of original artwork and handcrafted goods. This free two-day event will be showcasing local and national artists representing a variety of mediums including paintings, sculptures, photography, ceramics, glass, wood, and more. While browsing the artist booth […]
Halloween Bash Free for the whole family Trick-or-Treat Street Photo Booth Spooky DJ & Dance Party
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 shopping/dining giveaway to Cooper Creek Square and receive a half price voucher for the Comedy Show at Devil's Craft that starts at 8pm.
Celebration of Lights Visit with Santa, enjoy holiday music and explore the Square with the Elf on the Shelf scavenger hunt.
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 […]