June 20 – Tight Like That

Tight Like That

Award-winning Tight Like That returns to Grand County to kick off this summer’s Music on the Square. Bringing hot, sultry and swinging original tunes to rippling New Orleans Jazz and R&B. Bring your dancing shoes!

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 …