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. As the sun dips behind the mountains, the Square buzzes with locals and visitors alike, gathering to enjoy a variety of music genres. From the soulful strains of Blues and the intricate rhythms of Jazz to the upbeat tempos of pop and rock, each week offers a new musical experience. It's more than a concert; it’s a community event where families, friends and music lovers connect under the courtyard lights, surrounded by the beauty of the Rockies. Cooper Creek Square, a designated Entertainment District, permits guests to buy alcoholic beverages from any of our restaurants during the event and savor them in the courtyard. Our Cooper Creek restaurants offer a great take-out menu so you can enjoy a bite while you listen.