Pizza Night every Monday $3 off Pizza & $5 12oz Beers Enjoy live music from a variety of local talent.
Shopping & Dining in the Heart of Downtown Winter Park
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2 events,
Pizza Night every Monday $3 off Pizza & $5 12oz Beers Enjoy live music from a variety of local talent. The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season […] |
1 event,
The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season […] |
2 events,
Aperitivo happy hour menu every Wednesday and Thursday all night featuring a special menu. 2-for-1 wine pours, cocktail specials, plus $2 off all shareable plates and other special menu features […] The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season of the TV reality show, Last Comic Standing. Tickets are $45 at the door. Shows at 6pm & 8pm. |
4 events,
Bucket of Fried Chicken Night + somm paired champagne (special on menu) Aperitivo happy hour menu every Wednesday and Thursday all night featuring a special menu. 2-for-1 wine pours, cocktail specials, plus $2 off all shareable plates and other special menu features like our board + bottle The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season of the TV reality show, Last Comic Standing. Tickets are $45 at the door. Shows at 6pm & 8pm. Reggae Concert starring Mighty Mystic, Featuring local DJ and aerialists 9pm-midnight $10 Cover All ages |
5 events,
![]() Filet & Fondue Fridays Forty day dry-aged steak, fingerling potatoes, cubed bread, apple wedges, sausage, tomato, broccoli and shrimp. $75 / Serves 2
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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 […] The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season of the TV reality show, Last Comic Standing. Tickets are $45 at the door. Shows at 6pm & 8pm.
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Comedy Night starring Mitch Jones 8:30pm $15 thru Eventbrite, $20 at the door All ages |
4 events,
Seafood Boil & Tiki Bar It's patio season! Come enjoy a variety of seafood such as shrimp, crab, lobster, clams, mussels, and crawfish — along with vegetables including corn, potatoes, garlic, and mushrooms. All ingredients are boiled in a seasoned broth and served with lemon and parsley and fresh baguette.
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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 […] The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season […] Giant Walking Robots A High Energy Reggae/Synth/Dub/Rock Rooted in reggae, infused with jamtronica, and charged by drum and bass, Giant Walking Robots present a sound both familiar and forward-thinking. The […] |
4 events,
Somm Select Wine Feature with Buy One Glass get One Free Every Sunday Shelby will feature a wine along with a food pairing that will be a buy one glass […] Make plans to enjoy live harp music outside on Paella's patio with local Grand County artist every Sunday this summer. The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season […] |
2 events,
Pizza Night every Monday $3 off Pizza & $5 12oz Beers Enjoy live music from a variety of local talent. The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season […] |
1 event,
The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season […] |
2 events,
Aperitivo happy hour menu every Wednesday and Thursday all night featuring a special menu. 2-for-1 wine pours, cocktail specials, plus $2 off all shareable plates and other special menu features […] The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season […] |
4 events,
Game Night 5pm-close, Free Admission, Family-friendly through dinner hours / 21+ late-night Aperitivo happy hour menu every Wednesday and Thursday all night featuring a special menu. 2-for-1 wine pours, cocktail specials, plus $2 off all shareable plates and other special menu features […] Bucket of Fried Chicken Night + somm paired champagne (special on menu) The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season […] |
5 events,
![]() Filet & Fondue Fridays Forty day dry-aged steak, fingerling potatoes, cubed bread, apple wedges, sausage, tomato, broccoli and shrimp. $75 / Serves 2
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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 […]
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Join us every Friday from 8-11pm for our Piano bar experience complete with song requests, singalongs, craft cocktails, and (of course) amazing wine! We’re so excited to share this with […] The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season […] Live music by Dealer Takes Four Dealer Takes Four is a whiskey-driven rock band hailing from Denver, Colorado. This six-piece powerhouse is known for their raucous live shows. 9pm, $5 cover, 21+ |
4 events,
Seafood Boil & Tiki Bar It's patio season! Come enjoy a variety of seafood such as shrimp, crab, lobster, clams, mussels, and crawfish — along with vegetables including corn, potatoes, […]
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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 […] The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season […] |
4 events,
Somm Select Wine Feature with Buy One Glass get One Free Every Sunday Shelby will feature a wine along with a food pairing that will be a buy one glass […] Make plans to enjoy live harp music outside on Paella's patio with local Grand County artist every Sunday this summer. Open Mic Night with host Jed Henry @ 8pm, Free admission, All-night happy hour, All-ages The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season […] |
2 events,
Pizza Night every Monday $3 off Pizza & $5 12oz Beers Enjoy live music from a variety of local talent. The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season […] |
1 event,
The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season […] |
2 events,
Aperitivo happy hour menu every Wednesday and Thursday all night featuring a special menu. 2-for-1 wine pours, cocktail specials, plus $2 off all shareable plates and other special menu features […] The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season […] |
3 events,
Aperitivo happy hour menu every Wednesday and Thursday all night featuring a special menu. 2-for-1 wine pours, cocktail specials, plus $2 off all shareable plates and other special menu features […] Bucket of Fried Chicken Night + somm paired champagne (special on menu) The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season […] |
4 events,
![]() Filet & Fondue Fridays Forty day dry-aged steak, fingerling potatoes, cubed bread, apple wedges, sausage, tomato, broccoli and shrimp. $75 / Serves 2
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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 […] The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season […] Lance Rogers Band Lance Rogers is a Kentucky native and a country music singer-songwriter. He began writing in 2018 and quickly began gaining notoriety. Lance draws from his blue collar […] |
4 events,
Seafood Boil & Tiki Bar It's patio season! Come enjoy a variety of seafood such as shrimp, crab, lobster, clams, mussels, and crawfish — along with vegetables including corn, potatoes, […]
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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 […] The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season […] Diggin Dirt This California band is skyrocketing through the west coast music scene. They return to Winter Park for one night only! This seven-piece band emerging from behind the redwood […] |
3 events,
Somm Select Wine Feature with Buy One Glass get One Free Every Sunday Shelby will feature a wine along with a food pairing that will be a buy one glass […] Make plans to enjoy live harp music outside on Paella's patio with local Grand County artist every Sunday this summer. The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season […] |
2 events,
Pizza Night every Monday $3 off Pizza & $5 12oz Beers Enjoy live music from a variety of local talent. The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season […] |
1 event,
The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season […] |
2 events,
Aperitivo happy hour menu every Wednesday and Thursday all night featuring a special menu. 2-for-1 wine pours, cocktail specials, plus $2 off all shareable plates and other special menu features […] The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season of the TV reality show, Last Comic Standing. Tickets are $45 at the door. Shows at 6pm & 8pm. |
4 events,
Game Night with Giant Jenga, Mario Kart, board games, and more | 5pm-close | FREE admission | family-friendly during dinner hours, 21+ late-night Bucket of Fried Chicken Night + somm paired champagne (special on menu) Aperitivo happy hour menu every Wednesday and Thursday all night featuring a special menu. 2-for-1 wine pours, cocktail specials, plus $2 off all shareable plates and other special menu features like our board + bottle The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season […] |
4 events,
![]() Filet & Fondue Fridays Forty day dry-aged steak, fingerling potatoes, cubed bread, apple wedges, sausage, tomato, broccoli and shrimp. $75 / Serves 2
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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 […] The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season of the TV reality show, Last Comic Standing. Tickets are $45 at the door. Shows at 6pm & 8pm. Live Music by Jackson Harkness Meaningful lyrics delivered with high energy and passion 9pm-midnight / FREE admission / 21+ |
4 events,
Seafood Boil & Tiki Bar It's patio season! Come enjoy a variety of seafood such as shrimp, crab, lobster, clams, mussels, and crawfish — along with vegetables including corn, potatoes, garlic, and mushrooms. All ingredients are boiled in a seasoned broth and served with lemon and parsley and fresh baguette.
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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 […] The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season of the TV reality show, Last Comic Standing. Tickets are $45 at the door. Shows at 6pm & 8pm. Leadville Cherokee Leadville Cherokee is a rock band from Colorado that mixes the elements of rock, funk, country, and crustpunk with pure energy. The band counts Ween, Paul Cauthen, The Steeldrivers, and Bill Withers as guiding influences. 9pm-midnight / Admission $5 / 21+ |
2 events,
Somm Select Wine Feature with Buy One Glass get One Free Every Sunday Shelby will feature a wine along with a food pairing that will be a buy one glass get one free! The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season of the TV reality show, Last Comic Standing. Tickets are $45 at the door. Shows at 6pm & 8pm. |
2 events,
Pizza Night every Monday $3 off Pizza & $5 12oz Beers Enjoy live music from a variety of local talent. The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season of the TV reality show, Last Comic Standing. Tickets are $45 at the door. Shows at 6pm & 8pm. |
1 event,
The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season […] |
2 events,
Aperitivo happy hour menu every Wednesday and Thursday all night featuring a special menu. 2-for-1 wine pours, cocktail specials, plus $2 off all shareable plates and other special menu features […] The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season […] |
4 events,
Aperitivo happy hour menu every Wednesday and Thursday all night featuring a special menu. 2-for-1 wine pours, cocktail specials, plus $2 off all shareable plates and other special menu features […] Devil’s Craft Game Night with Giant Jenga, Mario Kart, board games, and more | 5pm-close | FREE admission | family-friendly during dinner hours, 21+ late-night Bucket of Fried Chicken Night + somm paired champagne (special on menu) The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season […] |
5 events,
![]() Filet & Fondue Fridays Forty day dry-aged steak, fingerling potatoes, cubed bread, apple wedges, sausage, tomato, broccoli and shrimp. $75 / Serves 2
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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 […] The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season […] |
4 events,
Seafood Boil & Tiki Bar It's patio season! Come enjoy a variety of seafood such as shrimp, crab, lobster, clams, mussels, and crawfish — along with vegetables including corn, potatoes, […]
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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 […] The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season […] |
3 events,
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Enjoy sidewalk sales, free face painting with Suzy-Q the Clown and live music with local favorite Andy Straus. Somm Select Wine Feature with Buy One Glass get One Free Every Sunday Shelby will feature a wine along with a food pairing that will be a buy one glass […] The Winter Park Comedy Festival concludes with the Peak Performance featuring Bonnie McFarlane. Bonnie is a Canadian comedian and writer. She is best know for appearing in the second season […] |