While Annapolis isn’t as significant of a city as nearby Baltimore and DC, its commitment to cultural beauty is evident in the many local theaters around town. One of the best things about regional theaters is that they offer both contemporary and classic productions as big city theaters, but at a smaller price.
ANNAPOLIS SUMMER GARDEN THEATRE (ASGT)
Summer will be here before you know it! The ASGT is a non-profit community theater located in the heart of downtown Annapolis on Compromise Street. Founded in 1966 in a historic barn that was once the Shaw Blacksmith Shop, the Theatre has become a staple of Annapolis entertainment. The theater puts on three shows yearly, offering family-friendly plays and musicals to thought-provoking adult dramas. They just announced their 2026 season with performances of Cabaret, Beautiful: The Carole King Musical, and Young Frankenstein.
143 Compromise Street | 410-268-9212
THE BOWIE PLAYHOUSE
The Bowie Playhouse is a 150-seat indoor theater that has operated since 1976. There are two resident companies at The Bowie Playhouse, Bowie Community Theatre and 2nd Star Productions. BCT produces comedies, murder mysteries and dramas. 2nd Star Productions produces mostly musicals. Both are supported through volunteer efforts and encourage new actors to audition. From
cabaret to cutting-edge drama, the Bowie Playhouse offers affordable productions for all.
16500 White Marsh Park Drive | 301-805-0219
THE COLONIAL PLAYERS
Initially founded in 1949 in an old car repair shop at the foot of the State House lawn, the Colonial Players Theatre offers a unique 365-degree stage setting for its productions. The Players bring in experiential theater, children’s programs, forums, and workshops in addition to traditional offerings, allowing for a diverse theater experience. Ticket prices are always low to encourage families and new theatergoers. Their musical, City of Angels, premieres March 5.
108 East St. | 410-268-7373
THE COMPASS ROSE THEATER
Founded in the spring of 2011, Compass Rose Theater is a small, non-profit professional theater that offers top-notch productions and workshops for students of all ages. Part of Compass Rose’s mission is to create opportunities for young talent to be a part of the professional theater world. You can currently see their production of the Broadway musical, Rent, in collaboration with Anne Arundel Community College.
801 Chase Street, 3rd Fl | 410-980-6662
THE CLASSIC THEATRE OF MARYLAND
Encompassing three different venues, the Classic Theatre of Maryland supports a year-round season of performance theater. With interpretations of classic works and bold, new contemporary plays, the CTM produces plays, musicals, and cabaret at their main theater on West Street, within Londontown’s Historic Gresham Estate, and in the courtyard of Reynold’s Tavern. Their production of A Tale of Two Cities starts on February 25.
1804 West St. | 410-280-1773
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