July 2019
Free Face Painting, Balloon Animals & Bouncy House
An afternoon of family fun at Cooper Creek Square. Shop, dine, or grab a gelato by the fountain and enjoy free face painting, balloon artist, fun family games, a bouncy house and a kids' playground and climbing boulders.
Find out more »August 2019
Yoga in the Park
Join us for a FREE yoga class in the courtyard at Cooper Creek Square. Mats are available for your use. All levels welcome.
Find out more »September 2019
Labor Day Block Party and Sidewalk Sale
Sidewalk sales, live music, face painting, balloon artist, Scavenger Hunt, family games, playground and bouncy house. FREE Event
Find out more »October 2019
Halloween Bash
Join us for trick-or-treating, fun family photos in the Photo Booth, DJ dance contests and more!
Find out more »December 2019
B Jammin / Moose Hollow Ladies Night
Grab your gal pals and come out to B Jammin and Moose Hollow on Thursday, Dec. 5 from 5-7pm for Ladies Night. Save 20% all night in both stores, amazing giveaways all night, free wrapping station, grand prizes at each store, and refreshments from Cooper Creek's newest restaurant, Ciao Monte.
Find out more »February 2020
Girl Scout Cookie Sales
It's Cookie Time! Come down to Cooper Creek Square from 2-5 pm and pick up your favorite selection of Girl Scout Cookies, while supplies last.
Find out more »Girl Scout Cookie Sales
It's Cookie Time! Stop by Cooper Creek Square and pick up your favorite Girl Scout cookie flavors and help support our local troops.
Find out more »March 2020
Girl Scout Cookie Sales
It's Cookie Time! Stop by Cooper Creek Square and pick up your favorite Girl Scout cookie flavors and help support our local troops.
Find out more »Girl Scout Cookie Sales
It's Cookie Time! Stop by Cooper Creek Square and pick up your favorite Girl Scout cookie flavors and help support our local troops.
Find out more »July 2020
Dinner and Live Music
Kick off your weekend with live music and dinner in the Courtyard at Cooper Creek Square. Enjoy dinner at one of Cooper Creek’s many outdoor dining locations with live music Fridays from 5-8 pm. New this summer is our extended outdoor dining area, which welcomes friends and family to enjoy take-out from any of our restaurants while socializing safely outside under our large outdoor tent! Your safety is of great concern, so we ask that you wear a mask when…
Find out more »Dinner and Live Music
Listen to live music with your dinner in the Courtyard at Cooper Creek Square. Enjoy dinner at one of Cooper Creek’s many outdoor dining locations with live music Fridays and Saturdays from 5-8 pm. New this summer is our extended outdoor dining area, which welcomes friends and family to enjoy take-out from any of our restaurants while socializing safely outside under our large outdoor tent! Your safety is of great concern, so we ask that you wear a mask when…
Find out more »Dinner and Live Music
Kick off your weekend with live music and dinner in the Courtyard at Cooper Creek Square. This Friday - Andy Straus Enjoy dinner at one of Cooper Creek’s many outdoor dining locations with live music Fridays from 5-8 pm. New this summer is our extended outdoor dining area, which welcomes friends and family to enjoy take-out from any of our restaurants while socializing safely outside under our large outdoor tent! Your safety is of great concern, so we ask that…
Find out more »Dinner and Live Music
Kick off your weekend with live music and dinner in the Courtyard at Cooper Creek Square. Tonight Peggy Mann and band takes the stage. Enjoy dinner at one of Cooper Creek’s many outdoor dining locations with live music Fridays from 5-8 pm. New this summer is our extended outdoor dining area, which welcomes friends and family to enjoy take-out from any of our restaurants while socializing safely outside under our large outdoor tent! Your safety is of great concern, so…
Find out more »August 2020
Dinner and Live Music
Listen to live music with your dinner in the Courtyard at Cooper Creek Square. Tonight enjoy Tyree Woods and Denton Turner from Buffalo Commons. Enjoy dinner at one of Cooper Creek’s many outdoor dining locations with live music Fridays and Saturdays from 5-8 pm. New this summer is our extended outdoor dining area, which welcomes friends and family to enjoy take-out from any of our restaurants while socializing safely outside under our large outdoor tent! Your safety is of great…
Find out more »September 2020
Live Music 5-8pm
Final weekend of live music at Cooper Creek for the summer. Enjoy the sounds of Blood Sugar with mother-daughter duo Retta and Emily Yarbrough from 5-8pm Enjoy dinner at one of Cooper Creek’s many outdoor dining locations with live music Fridays from 5-8 pm. New this summer is our extended outdoor dining area, which welcomes friends and family to enjoy take-out from any of our restaurants while socializing safely outside under our large outdoor tent! Your safety is of great…
Find out more »Live Music 5-8pm
Final night of live music in the Courtyard at Cooper Creek Square. Come out and hear local band, Moffat Tunnel Band and enjoy the final night of live music for the summer. Enjoy dinner at one of Cooper Creek’s many outdoor dining locations with live music Fridays and Saturdays from 5-8 pm. New this summer is our extended outdoor dining area, which welcomes friends and family to enjoy take-out from any of our restaurants while socializing safely outside under our…
Find out more »Thairapy Beauty Lounge Open House
Welcome Winter Park's newest salon, Thairapy Beauty Lounge, today from 9am-12pm.
Find out more »Thairapy Beauty Lounge Open House
Welcome Winter Park's newest salon, Thairapy Beauty Lounge, at an Open House today from 5pm-8pm.
Find out more »June 2021
Music on the Square
Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. 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, a bubbling fountain, and fresh mountain air. Musicians and audiences from across the country are drawn to this sweet summer music series that is sure to delight the senses. Schedule: June 25 - Andy Straus & Danjo…
Find out more »July 2021
Live Music 7-9pm
Enjoy free live music in the courtyard at Cooper Creek Square with Joe R and The Icebox Sound. Joe R and The Icebox Sound was founded by Joe Rooyakkers and Scott Torello. Joe and Scott’s paths crossed thanks to their passion for music when they shared the stage at a bar opening in Fraser, Colorado in 2000. After that first meeting they have played together ever since. The initial formation that was called Sasquatch Mountain Project has gone through many…
Find out more »Live Music 7-9pm
Enjoy free live music with local musician, Andy Straus & Friends, in the courtyard at Cooper Creek Square. Their music is well crafted and full of dynamic execution and harmony. Andy Straus plays every nook and cranny of the Colorado Rockies and beyond. Passionate about the groove, he like to sing hard and play his guitar hard. The amount of energy the they bring to the stage is unrivaled. Being a world traveler, his music can really explore genres, but he…
Find out more »Live Music 7-9pm
Enjoy live music with The Big Time Quartet. The Big Time Quartet is a funk/jazz fusion group based out of Denver Colorado and draws their influence from the likes of Steely Dan, Herbie Hancock, John Scofield, Grant Green, and The Meters to name a few. A relatively new project, though all of the members have toured the country in other groups extensively. With a mutual love amongst the members for the sounds of funk/jazz The Big Time Quartet was born…
Find out more »Live Music with Cowboy Brad & Mark Rashid 2-4pm
Enjoy live music with Cowboy Brad and Mark Rashid from Estes Park. Cowboy Brad: “I intend for my songs to express the wonder of being alive on this beautiful planet, and I hope they will help listeners to feel relaxed, comfortable and happy. If my music takes you to a pleasant place in your heart or your mind, then I have accomplished my purpose.” Raised in Estes Park, Colorado, singer, songwriter and guitarist Brad Fitch has been playing professionally since…
Find out more »Live Music with the Delta Sonics 2-4pm
The Delta Sonics music takes a Chicago Blues base and seasons it with Swing, Delta, N’awlins R&B and some early Rock n' Roll . They were Westword’s best blues band in Denver the last six of eight years. The band made the semi-finals in the Memphis (International Blues Challenge) in 2012. They have been featured at many of the major festivals in Colorado and Wyoming . Al Chesis supplies vocals & foot stomping showmanship but it's his harmonica playing that…
Find out more »Live Music 7-9pm
Enjoy the high energy sound of local musicians, the Moffat Tunnel Band. Moffat Tunnel Band melds all your favorite genres of music- rock, blues, R&B and everything in between. Creating noise that levels up every note with something fresh.
Find out more »August 2021
Live Bluegrass Music 7-9pm
Jason Hicks and KC Groves take the stage for what promises to be a great show. Bring your dancing shoes for a night of bluegrass! Jason Hicks, founding member of the Internationally touring bluegrass band Blue Canyon Boys, joins together with KC Groves,American mandolin player and singer. KC specializing in old-time music and bluegrass and was a founding member of Uncle Earl and living in Lyons, CO. Grab dinner, a drink and some friends and come enjoy an evening of…
Find out more »Music on the Square
Cowboy Dave Headlines Music on the Square Hard-swingin’ honky-tonk is a descriptor many country artists might shy away from in the current music landscape, but Cowboy Dave and his group of Rocky Mountain all-stars embrace the term with an exclamation mark. Opening for Cowboy Dave this Friday is the Trey Wanvig & the 9th Avenue Trio from 2:30-4:30pm. Trey Wanvig is a 19-year-old blues guitarist and vocalist from Sarasota, Florida and has performed at numerous blues and music festivals from…
Find out more »Live Blues Music 7-9pm
Come sample a taste of the next generation of Blues musicians with Trey Wanvig & the 9th Avenue Trio.
Find out more »Live Music 2-4pm
Enjoy the sweet sounds of Paul & Ieva Cataldo on stage in the courtyard at Cooper Creek Square. They play an upscale polished brand of Southern Rock, Country and Classic Rock. Paul Cataldo is an independent Americana singer/songwriter born and raised in South Eastern Massachusetts. He developed his Appalachian mountain influenced brand of backwoods wilderness inspired Americana while living inAsheville, NC through his late 20’s and early 30’s. Paul now records albums and tours for a living everywhere from Florida…
Find out more »Music on the Square
Madison Area Music Award winners, Tight Like That, returns to Cooper Creek with their sound that critics call “hot, sultry and swinging.” From original tunes to rippling New Orleans Jazz and R&B, Tight Like That will tickle your backbone and move your feet. Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana, to jazz and country in an intimate, outdoor…
Find out more »Live Music with The Andrew Duhon Trio
New Orleans native and singer/songwriter, Andrew Duhon, brings a refreshing honesty to his performance. His voice leaves no gaps in the experience as he sings with raw and personal conviction. His latest group, The Andrew Duhon Trio brings a new musicality to the tunes with upright bassist, Myles Weeks and drummer ,Maxwell Zemanovic. Since recording ‘The Moorings’ together as their first project, the Trio has been crossing the American landscape, touring and creating together, the thoughtful colors of the trio…
Find out more »September 2021
Music on the Square
Blood Sugar Kick Off Labor Day Weekend Retta and Emily, a mother and daughter duo bring a mix of Americana, Folk, and Blues; delivering mesmerizing and rich vocals 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 a mix of genres from blues and Americana, to jazz and country in an intimate, outdoor setting surrounded by beautiful flower gardens,…
Find out more »Live Music – 2 Great Shows
2pm-5pm - Glen T and the Soundsations 7pm-9pm - Delta Sonics Keep the fun going this Labor Day weekend with live music all day at Cooper Creek Square. Starting at 2pm, enjoy Glen T and the Soundsations in the courtyard. The greatest hits from famous artists of the last 5 decades, plus originals performed in a classy soft-rock style Glen T. has been entertaining people with music since his age was in the single digits and he has enjoyed the ride…
Find out more »October 2021
Halloween Bash
It's back! Halloween Bash at Cooper Creek Square. Wear your best costume and come down for some fun trick-or-treating and spooky Halloween music. We look forward to seeing everyone again this year.
Find out more »November 2021
Celebration of Lights
Grab the kids and head to Cooper Creek to celebrate the season with a visit from Santa, an Elf on the Shelf scavenger hunt, holiday music with local DJ and the lighting of our canopy of lights.
Find out more »December 2021
Shop & Sip Holiday Open House
Experience holiday shopping at Cooper Creek Square. Register to Win a $100 Cooper Creek Square Shopping or Dining gift certificate, while shopping for unique holiday gifts. Grab a beverage from your favorite Cooper Creek Square restaurant to enjoy while you shop. Play the Elf on the Shelf scavenger hunt to win a holiday gift. Each store will be offering their own special touch to the Open House so stop by and see what's new this season. Some offerings: B Jammin -…
Find out more »March 2022
Candlelight Vigil to Support Ukraine
Tentative timeline 6:00 People arrive 6:15 Impromptu speakers/prayer/music 6:25 Starting of candle light 6:45 Moment of Silence 6:55 People can exit in silence or stick around to decorate a Bring Back the Smile Card at Big Trout Brewery. There will be postcards available for adults and kids to decorate. These postcards will be delivered with other supplies heading to Finland and Poland very soon. The smile cards will go directly in the hand of Ukrainian refugees.
Find out more »June 2022
Music on the Square
Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana, to jazz and country in an intimate, outdoor setting. Check out the line up at Music on the Square.
Find out more »Music on the Square
Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana, to jazz and country in an intimate, outdoor setting. Check out the line up at Music on the Square.
Find out more »July 2022
Music on the Square
Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana, to jazz and country in an intimate, outdoor setting. Check out the line up at Music on the Square.
Find out more »Music on the Square
Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana, to jazz and country in an intimate, outdoor setting. Check out the line up at Music on the Square.
Find out more »Music on the Square
Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana, to jazz and country in an intimate, outdoor setting. Check out the line up at Music on the Square.
Find out more »Music on the Square
Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana, to jazz and country in an intimate, outdoor setting. Check out the line up at Music on the Square.
Find out more »Music on the Square
Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana, to jazz and country in an intimate, outdoor setting. Check out the line up at Music on the Square.
Find out more »Music on the Square
Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana, to jazz and country in an intimate, outdoor setting. Check out the line up at Music on the Square.
Find out more »Music on the Square
Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana, to jazz and country in an intimate, outdoor setting. Check out the line up at Music on the Square.
Find out more »Music on the Square
Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana, to jazz and country in an intimate, outdoor setting. Check out the line up at Music on the Square.
Find out more »Music on the Square
Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana, to jazz and country in an intimate, outdoor setting. Check out the line up at Music on the Square.
Find out more »Music on the Square
Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana, to jazz and country in an intimate, outdoor setting. Check out the line up at Music on the Square.
Find out more »August 2022
Music on the Square
Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana, to jazz and country in an intimate, outdoor setting. Check out the line up at Music on the Square.
Find out more »Music on the Square
Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana, to jazz and country in an intimate, outdoor setting. Check out the line up at Music on the Square.
Find out more »Music on the Square
Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana, to jazz and country in an intimate, outdoor setting. Check out the line up at Music on the Square.
Find out more »Music on the Square
Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana, to jazz and country in an intimate, outdoor setting. Check out the line up at Music on the Square.
Find out more »Music on the Square
Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana, to jazz and country in an intimate, outdoor setting. Check out the line up at Music on the Square.
Find out more »Music on the Square
Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana, to jazz and country in an intimate, outdoor setting. Check out the line up at Music on the Square.
Find out more »Music on the Square
Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana, to jazz and country in an intimate, outdoor setting. Check out the line up at Music on the Square.
Find out more »Music on the Square
Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana, to jazz and country in an intimate, outdoor setting. Check out the line up at Music on the Square.
Find out more »September 2022
Music on the Square
Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana, to jazz and country in an intimate, outdoor setting. Check out the line up at Music on the Square.
Find out more »Music on the Square
Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana, to jazz and country in an intimate, outdoor setting. Check out the line up at Music on the Square.
Find out more »Labor Day Block Party
Spend your holiday weekend at Cooper Creek Square. On Sunday, Sept. 4 we'll have live music with Burnt Orange and renowned face painter, Suz-Q-Z the Clown, plus sidewalk sales throughout the Square.
Find out more »Winter Park Arts Festival
The Winter Park Art Festival is a 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. Cooper Creek Square makes for the perfect backdrop for this celebration of art, craft, live music, and community fun. Attendees of the event will be able to enjoy their favorite beverage from any…
Find out more »Winter Park Arts Festival
The Winter Park Art Festival is a 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. Cooper Creek Square makes for the perfect backdrop for this celebration of art, craft, live music, and community fun. Attendees of the event will be able to enjoy their favorite beverage from any…
Find out more »October 2022
Halloween Bash
Join us for trick-or-treating, DJ Dance Party, Photo Booth and so much fun!
Find out more »November 2022
Ladies Night
Join us for Ladies Night! Register to win a $100 shopping or dining certificate for Cooper Creek Square. Play the Elf on the Shelf scavenger hunt and take home a holiday ornament and receive a free drink coupon for any of our restaurants. Each store will be offering their own unique touch to the night so stop by to see what's new and start your holiday shopping locally. And for a special treat, grab your friends and join the ladies…
Find out more »Celebration of Lights
Celebration of Lights Light display and Christmas tree lighting. Visit with Santa. Kids play the Elf on the Shelf scavenger hunt and take home a holiday gift.
Find out more »December 2022
Fraser Valley Elementary Choir Show
Cooper Creek Square welcomes the Fraser Valley Elementary choir for a special holiday performance around the fountain.
Find out more »June 2023
Street Comedy @ Cooper Creek
Stop by Cooper Creek Square to hear a variety of street comics performing family friendly comedy. You may also see Comedy Festival comics coming in and out to promote their other shows coming up throughout the festival.
Find out more »Street Comedy @ Cooper Creek
Stop by Cooper Creek Square to hear a variety of street comics performing family friendly comedy. You may also see Comedy Festival comics coming in and out to promote their other shows coming up throughout the festival.
Find out more »Music on the Square
Blues Allstars This show features young musicians from all around the US playing an array of music including Blues, Top 40 and Americana. Brought to you by the Grand County Blues Society. Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. 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, a bubbling fountain, and fresh…
Find out more »Music on the Square
Puddle Stomp With decades of experience, this trio thrives on rock, funk, and soul-driven improvisational jams. From creative original pieces to reimagined classics, the band aims to please people in the crowd as well as share their enjoyment of the performance. Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana to jazz and country in an intimate, outdoor setting surrounded…
Find out more »Music on the Square
Reed Foehl With a life dedicated to songwriting and music, Reed has five studio albums which include the Grammy nominated song “Fly”, co-written with Brent Cobb and covered by country legend Lee Ann Womack. His folk/Americana music tells stories while paying homage to the tradition. Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana to jazz and country in an…
Find out more »July 2023
Music on the Square
Andy Straus A spicy blend of influences that has been dubbed “Rocky Mountain Folk-n-Roll”. Based in Bluegrass, good songwriting, and soulful country rock, they have found a way to harness the groove that shakes your hips and touches your heart. Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana to jazz and country in an intimate, outdoor setting surrounded by…
Find out more »First Fridays
First Friday brought to you by Uptripping. Local artists. Live music.
Find out more »Music on the Square
Delta Sonics Voted Denver’s Best Blues Band (Westword) 6 times! The Delta Sonics music takes a Chicago Blues base and seasons it with Swing, Delta N’awlings R&B and some early Rock-n-Roll. Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. 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, a bubbling fountain, and fresh mountain…
Find out more »Music on the Square
Mark Oblinger A 5-time Emmy winning, and Grammy nominated composer and producer, Mark brings his soulful, eclectic blend of Folk-Pop to the stage, featuring powerful, vocal forward arrangements. Mark’s national performing roots include stints with Pure Prairie League and Firefall. Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. 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,…
Find out more »Music on the Square
Altameda This unique Canadian band brings raw, candid performances wrapped inside gorgeous, gently atmospheric arrangements. Their lyrics often grapple with our dueling desires for connection and escape through visceral, cinematic imagery that finds meaning in the mundane. Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. 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,…
Find out more »Music on the Square
Kory Montgomery Known for his solid grooves, intense solos and demanding lyrics, Kory’s music has been described as Blues-Funk-Jazz Fusion. He’s opened for the legendary BB King, Kenny Wayne Shepard, Earth Wind & Fire, and many other national acts. Rock on! Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana to jazz and country in an intimate, outdoor setting surrounded…
Find out more »Music on the Square
Haley Johnsen Haley’s soaring vocals and introspective lyricism is steeped in a cross of Indie-Pop and Folk-Rock. Her eclectic style has taken her from the top 24 on American Idol in 2012, to three highly acclaimed albums; landing her as the bassist and back up vocalist for the band Big Wild in 2019, playing festivals such as Lollapalooza, Coachella, Bonnaroo, and several sold out shows at Red Rocks. Music on the Square is a summer concert series tradition at Cooper…
Find out more »Music on the Square
Andrew Duhon For over a decade New Orleans singer/songwriter Andrew Duhon has been performing on this stage. Every year he brings new songs full of deep and soulful stories. His lyrics and style have been compared to that of John Prine and Jim Croce with a rich and powerful voice evoking a young Van Morrison. Out with a new album, Emerald Blue, he expands even beyond where he was before. Music on the Square is a summer concert series tradition…
Find out more »Music on the Square
Wood Belly Honest, soulful, and bearing a sound all their own, Wood Belly sprouted from the roots of bluegrass to notch a unique home in the broader Americana scene and continues to captivate audiences across the country. Forging a sound that is based in newgrass, flavored with alt-country, rock, and just enough jam to glue it all together. Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a…
Find out more »Music on the Square
Bill McKay with Jack Watson on drums Boogie from Blues to Bluegrass. Bill McKay has been a part of the Colorado music scene for 30 years. Playing with Derek Trucks Band, Band du Jour, Leftover Salmon and so many more incredible artists, he keeps moving forward in his pursuit of musical adventure! Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and…
Find out more »August 2023
First Fridays
First Friday brought to you by Uptripping. Local artists. Live music.
Find out more »Music on the Square
Family Recipe Cooking up a great mix of jams that is often described as Southadelic Rock. The four-piece band plays their own originals with a mix of fun twists on many of your favorite jam bands including The Grateful Dead, Phish, Widespread Panic, Allman Brothers, and others. Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana to jazz and country…
Find out more »Music on the Square
Osborne & Key A staple in our local music scene, Sam & Gary have been playing music together for over two decades. They sing a wide selection of your favorite songs from Classic Rock to Country, Blues and more. Bring your dancing shoes! Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana to jazz and country in an intimate, outdoor…
Find out more »Music on the Square
Eilen Jewell Hailed by American Songwriter as “one of America’s most intriguing, creative, and idiosyncratic voices,” Eilen Jewell rises from the ashes after a series of hardships and triumphs revealed on her new album, Get Behind the Wheel. Jewell combines vintage roots-noir with spacious, cinematic arrangements. Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana to jazz and country in an…
Find out more »Music on the Square
Goat Trail Hailing from Evergreen, Colorado, Goat Trail has been jamming together since 2013. A classic Rock ‘n’ Roll band covering decades of music from the 70s to the early 2000s with a scattering of some hefty originals. Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana to jazz and country in an intimate, outdoor setting surrounded by beautiful flower…
Find out more »Music on the Square
Strangebyrds A staple to the Cooper Creek stage, Strangebyrds are award-winning singer-songwriters and multi-instrumentalists that craft songs with a unique Americana sound they call "Blue Collar Folk". The magnetic synergy of their music has forged a reputation for captivating audiences with powerful, universal truths layered within stunning musicianship. Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana to jazz and…
Find out more »Music on the Square
Joe R and the Icebox Sound Joe R and the Icebox Sound play original music as well as covering well known songs by familiar Americana artists. This amazing collection of artists play guitar, fiddle, upright bass, harmonica, and light percussion. Their sound will get your toes tapping. Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana to jazz and country…
Find out more »Music on the Square
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 at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana to jazz and country in an…
Find out more »Music on the Square
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 tasty, little, mid-'70s, ‘Rock’ biscuit with some creamy ‘Pop’ drizzle.” Music on the Square is a summer concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana to jazz and country in an intimate, outdoor setting surrounded by beautiful…
Find out more »September 2023
First Fridays
First Friday brought to you by Uptripping. Local artists. Live music.
Find out more »Music on the Square
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 Park. Enjoy music from a mix of genres from blues and Americana to jazz and country in an intimate, outdoor setting surrounded by beautiful flower…
Find out more »Music on the Square
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 concert series tradition at Cooper Creek Square, in downtown Winter Park. Enjoy music from a mix of genres from blues and Americana to jazz and…
Find out more »Labor Day Block Party & Sidewalk Sales
Enjoy sidewalk sales, free face painting with Suzy-Q the Clown and live music with local favorite Andy Straus.
Find out more »Winter Park Art Festival
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 grab a beverage from any of the Cooper Creek Square restaurants and enjoy live music both days from 1-4pm.
Find out more »Winter Park Art Festival
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 grab a beverage from any of the Cooper Creek Square restaurants and enjoy live music both days from 1-4pm.
Find out more »October 2023
Halloween Bash
Halloween Bash Free for the whole family Trick-or-Treat Street Photo Booth Spooky DJ & Dance Party
Find out more »November 2023
Ladies Night @ Cooper Creek Square
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.
Find out more »Celebration of Lights
Celebration of Lights Visit with Santa, enjoy holiday music and explore the Square with the Elf on the Shelf scavenger hunt.
Find out more »December 2023
Stuff-a-Bus Toy Drive
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 Toy Drive.
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