Labor Day weekend is just around the corner, and Cooper Creek Square is the perfect destination for families & friends, offering a jam-packed holiday filled with thrilling music, shopping, and delightful dining experiences! Nestled in the heart of downtown Winter Park, Colorado, our vibrant square not only provides a perfect blend of entertainment, food, and shopping but will also be hosting several Free events (Music on the Square, Saturday Sessions, & our annual Labor Day Block Party) and entertainment throughout the weekend, ensuring an unforgettable experience for everyone!
Friday, August 29th: Kick Off the Weekend with Music on the Square
Start your weekend off right with Music on the Square from 6 to 8 PM, featuring the electrifying sounds of Mama Lenny & the Remedy. This talented seven-piece band delivers a high-energy fusion of soul, funk, rock, blues, and disco, with hints of jazz, gospel, and Broadway. Their infectious energy and witty lyrics will have you dancing and singing along in no time.
Afterward, head over to Devil’s Craft for DJ Timmy Bean’s Holiday Weekend Kickoff. Situated on the lower level of Cooper Creek Square, Devil’s Craft is Winter Park’s nightlife hotspot, offering a lively atmosphere with craft cocktails and a full weekend of events to keep the party going all night long.
Saturday, August 30th: Double the Fun with Saturday Sessions
Saturday promises a double dose of musical magic with our Saturday Sessions:
- Easy Tiger from 3 to 5 PM: This acoustic band brings high energy and heart, straight from the wild jungles of Colorado. Their vibrant melodies and engaging performances are not to be missed.
- Steve Postell from 6 to 8 PM: With a career spanning songwriting, production, and performance, Steve Postell has played alongside legends like David Crosby and Kenny Loggins. Enjoy his soulful tunes and masterful guitar work.
Later that evening, Dustbowl Revival takes the stage at Devil’s Craft with their unique blend of folky-funk and rock ‘n’ soul. Their New Orleans-tinted brass section and fearless lyrics will keep you grooving all night.
Sunday, August 31st: Labor Day Block Party & Sidewalk Sales
Join us for a festive Labor Day Block Party & Sidewalk Sales featuring live music by Joe R & the Icebox Sound. The day will be filled with family-friendly activities, including face painting, balloon artists, and a bouncy house. Don’t forget to explore the Sidewalk Sales from our amazing Cooper Creek Square shops, offering an incredible array of goods, souvenirs, and locally-made items.
Wrap up the holiday weekend at Devil’s Craft for their Summer 2025 Season Finale Show with Dealer Takes Four, a local favorite band delivering a one-of-a-kind mash-up of rock and roll, country, groove, and Americana.
Dining and Shopping Delights
While you’re here, explore Cooper Creek Square’s Restaurant Row, boasting 8 diverse dining options ranging from Asian fusion to Mexican delights. Whether you’re in the mood for a gourmet meal or a casual bite, our restaurants offer something for every palate.
And when it comes to shopping, Cooper Creek Square is home to 12 unique shops offering everything from handcrafted jewelry to outdoor gear. Discover unique and locally-made items that capture the essence of Winter Park.
Find all the details for Cooper Creek Square’s events, shops, and restaurants at www.CooperCreekSquare.com!
This Labor Day weekend, make Cooper Creek Square your go-to destination for fun, food, and festivities. We can’t wait to celebrate with you!
