Theater, Music and Art

Mainstay, Rock Hall
The Mainstay is a warm friendly place with great sound and sight lines. With only 120 seats, there’s not a bad one in the house. It’s a listening room that’s almost as comfortable as your living room. Beer, wine and soft drinks are available. Our audiences range from local Rock Hallers to those who find their way here from Philadelphia, Annapolis, Baltimore, Washington DC and beyond. 410-639-9133.

Prince Theatre, Chestertown
A wonderful old vaudeville theater, renovated and now presenting a wide range of concerts and live performances of jazz, live theater, dance, as well as films. 410-810-2060.

Chester 5 Movie Theater
410-778-2227

Church Hill Theatre
Performing arts center in a sleepy eastern shore town. Live theater and musical productions presented in this beautifully-restored art deco theater, on the national register of historic places. 410-758-1331.

Fountain Park Outdoor Concerts
For schedule of performances, click here.

"First Friday"
A monthly celebration in Chestertown. Every first Friday of the month shops and galleries stay open late and the local artists are available to meet with the public. Several of the shops serve wine and cheese plates. There is also a small theatre that hosts local musicians.

Local Arts Calendar