Music on the Square

Cowboy Dave

Cowboy Dave and his band of honky-tonk all-stars are poised to put the western back in country and western. The group brings a plethora of experience to its high-energy live show, drawing on classic country music influences, ranging from the Bakersfield sound to Western Swing. 

FREE line dancing class, 5-6 pm 

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.

Shows will go on rain or shine – we are hardy here at 9,000 feet unless it is a massive downpour and the venue cancels due to safety concerns. This series is free and everyone is welcome.

Cooper Creek Square is a designated Entertainment District which allows guests to purchase alcoholic beverages from any of our restaurants during the show and enjoy them in the courtyard