Top 5 Entertainment Venues in and around Chestertown, MD

Historic High Street, Chestertown, MD

See a play. Watch a movie. Hear the chorale. View an old silent film. Dance to a swing band. Go to an open-mic night. All answers to the most frequently asked question: “If I come to Brampton Bed and Breakfast Inn, what is there to do?”

Here are the Top 5 Entertainment Venues in Chestertown, MD:

1. The Garfield Center for the Performing Arts, formerly known as the Prince Theater, in downtown Chestertown, MD, only 1½ miles from our historic eastern shore bed and breakfast. A wide range of local, regional, and international acts perform in this beautifully restored old theater, so on any given night it could range from local open-mic  night to  “Short Attention Span Theater” to the world’s greatest harmonica player.

2. The Mainstay, a music venue on the main street named Rock Hall, is yet another place to see locals as well as international musicians. Brampton Bed and Breakfast Inn employees (the locals) are looking forward to seeing Ramblin’ Jack Elliot in May 2012. This place only has 120 seats, so tickets will go fast!

3. About 7 miles from Chestertown, MD, is the city of Church Hill, which houses the historic Church Hill Theater and offers several plays each year. It’s simply good, old-fashioned community theater.

4. A bit further afield, just under an hour from our eastern shore bed and breakfast, is the Avalon Theater in Easton, MD, and is known as the “Showplace of the Eastern Shore.” A beautifully restored Art Deco theater, the Avalon hosts concerts, theater, and even opera from the Met via HD feed!  It’s also the main theater for screenings at the Chesapeake Film Festival.

5. And if you’re in the mood for the latest blockbuster, The Chester 5, our local Chestertown movie theater is about 5 minutes from here. Aptly named with 5 theaters, it is a bit time-worn, but tickets are only $7.50 and $5.50 for a matinee on the weekends.

There you have it. Not bad, huh? And that’s not even including the free summer music series in Fountain Park or the many free lectures and films over at Washington College.

So this summer, if you’re in our area and it’s a rainy day, have no fear. At Brampton Bed and Breakfast Inn, we’ll find something enjoyable for you to do!


Dine in Style! 

If you are looking for a unique dining experience, we have two amazing dining-series this season!

Check out Dining Under the Stars with Chef Kurt Peter starting May 2!


Gourmet Diner Club with chef Jordan Lloyd starting May 23!

Dining and entertainment experiences to remember! See our Specials page.

Book Now

Want to be the first to know about specials and events? Sign Up Now