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July 2024
Music on the Square
Music on the Square is a cherished summer concert series tradition in downtown Winter Park. Join us every Friday night, from 6pm-8pm, June 21-Aug. 30. July 26 | The Two Tracks This Wyoming-based band brings songs that traverse a wide range perspective with emotional and natural images of rural American life. Their live shows feature an array of sounds, from introspective ballads to foot-stomping anthems. Songs that reflect their earthy authenticity and a genuine love for their craft. As the…
Find out more »Saturday Sessions
The music continues with the Saturday Sessions from 4-6 PM. This series features a more laid-back setting, inviting you to relax by the fountain, enjoy a meal or a drink from one of the many Cooper Creek eateries, and immerse yourself in the sounds of up-and-coming artists as well as established performers. It's the perfect way to unwind after a day exploring the trails or shopping in our unique local businesses. Kids will enjoy the playground. July 27 | Osborne…
Find out more »August 2024
Music on the Square
Music on the Square is a cherished summer concert series tradition in downtown Winter Park. Join us every Friday night, from 6pm-8pm, June 21-Aug. 30. Aug. 2 | Blood Sugar This mother and daughter duo can bring down the house with that bring a mix of Americana, Folk, and Blues; delivering rich vocals and mesmerizing and harmonies that could only come from shared DNA. With a new album under their belt, you don’t want to miss this local favorite. As…
Find out more »Saturday Sessions
The music continues with the Saturday Sessions from 4-6 PM. This series features a more laid-back setting, inviting you to relax by the fountain, enjoy a meal or a drink from one of the many Cooper Creek eateries, and immerse yourself in the sounds of up-and-coming artists as well as established performers. It's the perfect way to unwind after a day exploring the trails or shopping in our unique local businesses. Kids will enjoy the playground. Aug. 3 | Mark…
Find out more »Music on the Square
Music on the Square is a cherished summer concert series tradition in downtown Winter Park. Join us every Friday night, from 6pm-8pm, June 21-Aug. 30. Aug. 9 | Grant Sabin Trio Drawing from his Delta Blues influences, Sabin's unique musical style is characterized by biting slide guitar, a soulful growl, and heartfelt lyrics. His honest and convincing approach to the Blues, Folk, Hip-Hop and Rock genres make him a unique musical talent. As the sun dips behind the mountains, the…
Find out more »Saturday Sessions
The music continues with the Saturday Sessions from 4-6 PM. This series features a more laid-back setting, inviting you to relax by the fountain, enjoy a meal or a drink from one of the many Cooper Creek eateries, and immerse yourself in the sounds of up-and-coming artists as well as established performers. It's the perfect way to unwind after a day exploring the trails or shopping in our unique local businesses. Kids will enjoy the playground. Aug. 10 | Family…
Find out more »Music on the Square
Music on the Square is a cherished summer concert series tradition in downtown Winter Park. Join us every Friday night, from 6pm-8pm, June 21-Aug. 30. Aug. 16 | Last Call Romance Known for their modern take on a mid-century sound, along with original songs about love, heartache and everything in between. Last Call Romance delivers an Indie-Bluesy Swing and energetic performances are always a crowd pleaser. Listen Here As the sun dips behind the mountains, the Square buzzes with locals…
Find out more »Farmers Market
Join us for our first annual Farmers Market from 4-6pm. Peruse an intimate selection of vendors including fresh bread, cookies, meat & cheese, and jerky while enjoying live music, aerial performance and balloon creations for the kids.
Find out more »Music on the Square
Music on the Square is a cherished summer concert series tradition in downtown Winter Park. Join us every Friday night, from 6pm-8pm, June 21-Aug. 30. Aug. 23 | Steve Postell During Steve’s long career as a songwriter, performer, and producer, he has played with artists including David Crosby, Jennifer Warnes, John Oates, and Kenny Loggins. He is currently touring and recording as a member of the All-Star band, The Immediate Family. "Postell's songs are full of warmth and intimacy." - ROLLING STONE…
Find out more »Saturday Sessions
The music continues with the Saturday Sessions from 4-6 PM. This series features a more laid-back setting, inviting you to relax by the fountain, enjoy a meal or a drink from one of the many Cooper Creek eateries, and immerse yourself in the sounds of up-and-coming artists as well as established performers. It's the perfect way to unwind after a day exploring the trails or shopping in our unique local businesses. Kids will enjoy the playground. Aug. 24 | Joe…
Find out more »Saturday Sessions
The music continues with the Saturday Sessions from 4-6 PM. This series features a more laid-back setting, inviting you to relax by the fountain, enjoy a meal or a drink from one of the many Cooper Creek eateries, and immerse yourself in the sounds of up-and-coming artists as well as established performers. It's the perfect way to unwind after a day exploring the trails or shopping in our unique local businesses. Kids will enjoy the playground. Aug. 31 | Peggy…
Find out more »September 2024
Labor Day Block Party & Sidewalk Sales
Enjoy an afternoon of sidewalk sales, live music and face painting / balloon creations for the kids.
Find out more »Winter Park Art Festival
Winter Park Art Festival Amazing art, handcrafted goods and great live music. Free Admission
Find out more »Winter Park Art Festival
Winter Park Art Festival Amazing art, handcrafted goods and great live music. Free Admission
Find out more »