Chaska

Chaska's live-music options run through two neighborhood bar-and-grills. Cy's Bar and Grill sits in the historic Mill Building in downtown Chaska, where a u-shaped bar and laid-back setup anchor a room that hosts live music, karaoke, and trivia nights. Pool tables and lots of TVs fill the space, and weekends tend to bring special events and music. Heartbreakers Bar & Grill, at 222 Pioneer Trail, books live acts on a recurring basis, with pool tables, dart boards, trivia, and bingo rounding out the calendar. Visiting acts have included jazz bands as well as acoustic performers like Tyler Herwig, who is rooted in the indie country and pop scene. Heartbreakers also runs karaoke and happy-hour programming alongside its live shows. Both spots lean local and unpretentious, serving the kind of neighborhood bar crowd that keeps a smaller suburb's after-hours scene running.