Shopping & Dining in the Heart of Downtown Winter Park
String Fling This four-piece acoustic string band brings a collective 200+ years of experience and a “we ain’t dead yet” attitude to bare on an extensive blend of Americana, Classic Folk, and Country to contemporary music. Originals and classics alike will quench your thirsty ears! Music on the Square is a summer concert series tradition […]
Peggy Mann Band Whatever style of music you enjoy, you’ll hear it at Peggy Mann’s shows along with many original songs found on one of seven albums. Mann is the winner of numerous vocalist and song writing awards and her band has been the winner of “The Best Band of Grand County” for six straight years. […]
$3 Off Pizza and $1 Off 12oz Beers • Plus Live Music
Karaoke Night with Travis Taylor Wednesdays in Winter Park get wild at Devil's Craft. Host/DJ Travis Taylor kicks off the party at 8pm. Then it's up to you to keep the dance floor jumpin'! What will you be singing this Wednesday to bring out your inner rockstar?... Happy Hour til 8pm Karaoke sign-up 8pm-midnight Full […]
Blood Sugar This mother and daughter duo can bring down the house with a mix of Americana, Folk, and Blues; delivering rich vocals and mesmerizing and harmonies that could only come from shared DNA. Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from […]
Fundraising for Tame Wellness! Join us for this donation-based Yoga in Cooper Creek Square Courtyard a few Summer Saturdays @ 9:30 a.m. No registration necessary. You can also enjoy a discount at Monarch Lake Chocolate & Coffee and Ascending Spirit when you show your Tame stamp (given at the end of yoga). It's a great […]
Justin Roth Justin Roth is a nationally touring singer/songwriter/acoustic guitarist based in Colorado. His brilliantly inventive fingerstyle guitar arrangements define his unique mix of indie folk and instrumental guitar music. 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, […]
$3 Off Pizza and $1 Off 12oz Beers • Plus Live Music
Karaoke Night with Travis Taylor Wednesdays in Winter Park get wild at Devil's Craft. Host/DJ Travis Taylor kicks off the party at 8pm. Then it's up to you to keep the dance floor jumpin'! What will you be singing this Wednesday to bring out your inner rockstar?... Happy Hour til 8pm Karaoke sign-up 8pm-midnight Full […]
Mama Lenny & the Remedy Seven-piece powerhouse Mama Lenny and the Remedy deliver a high-energy fusion of soul, funk, rock, blues, and disco with hints of jazz, gospel, and Broadway. With infectious energy, the band delves into the joys and downfalls of love and life−always with a wink of humor and a witty turn of […]
Easy Tiger - 3-5pm An acoustic band with high energy and high heart, hailing from the wild jungles of Colorado. Steve Postell - 6-8pm With a long career as a songwriter, producer and performer, Steve has played with artists including David Crosby, Jennifer Warnes, John Oats and Kenny Loggins.
Labor Day Block Party & Sidewalk Sales Live music with Joe R & the Icebox Sound Face painting & Balloon artists Bouncy House Sidewalk Sales