What Are the Best Chestertown, Maryland, Theaters?

If you’re looking for the perfect way to spend a chilly evening or a date night to remember, there’s nothing quite like catching a movie or local performance! The Eastern Shore of Maryland is an incredible place to celebrate the arts—whether it’s a fabulous film on the silver screen or a lively production on the local stage. Below, we’ve compiled all of the best Chestertown, Maryland, theaters so you’ll have some top-notch choices for date night when you’re in town! For more local insight, be sure to:

Claim Your Free Guide to The Eastern Shore of Maryland!

Where to See a Movie in Chestertown

Chesapeake Movies

Movie night at this small, local theater isn’t just movie night—it’s an experience defined by total comfort and relaxation. The reclining, cushy seats in the reserved section of this movie theater make for a truly one-of-a-kind viewing encounter! Though unassuming at a glance, there’s no better spot than Chesapeake Movies (formerly known as the Chester 5 Theater) if you find yourself in the mood for a flick. Find it at 21 Washington Square in Chestertown, just a 6-minute drive away from Brampton Inn.

Where to See a Play in Chestertown

Garfield Center for the Arts at the Prince Theatre

If a live performance is more your speed, not to worry: Chestertown is a hotbed for the performing arts! If you and yours love the idea of catching a memorable play during your trip to Chestertown, The Garfield Center for the Arts at the Prince Theatre is where you need to go. This historic theater hosts productions and other Chestertown events for both youth and adults to enjoy all year long! In addition to stage productions, this theater often shows classic movies, live music, and an open-mic night. There are even plenty of snacks and beverages served in the lobby if a craving hits. There’s always something worthwhile happening at the Prince Theatre! Be sure to swing by 210 High Street for a production next time you’re in town. It’s only a quick 6-minute drive away from Brampton Inn (and within walking distance of Chestertown’s best attractions like Washington College).

Where to See Live Music in Chestertown

The Mainstay in Rock Hall

Though not technically in Chestertown, The Mainstay in Rock Hall should definitely be at the top of your list if you plan on checking out the Eastern Shore’s live entertainment scene! Here, you’ll encounter phenomenal guest artists and local celebrities like Joe Holt. The best part about adding this fun and funky spot to your itinerary? Brampton Inn offers two complimentary tickets when you add our Mainstay Monday Special to your reservation!

Come Back to Comfort and Genuine Hospitality at Brampton Inn!Russell's Cottage at Brampton Inn, close to the Chestertown, Maryland, Farmers Market and Other Chestertown, MD, Things to Do and Chestertown, Maryland, Theaters

After a night out on the town, you’ll need a comfortable, warm, and welcoming place to stay. Here at Brampton Inn, our guests are treated like family! You’ll love retreating to your bright, airy, and spacious guest room or cozy cottage and enjoying the premium amenities we offer. Every morning of your stay, you’ll wake up to fresh, country air and our homemade, gourmet breakfast featuring lovingly prepared dishes and handmade treats. After you settle in, you’ll love sitting back, relaxing, and “porch surfing” with us (trust us….it’s a thing)! During special times of the year, Brampton Inn also hosts a variety of festive events. Isn’t it time you came to experience them for yourself?

Ready to explore the artistic side of Maryland’s Eastern Shore? Check our availability today and start planning your getaway! We can’t wait to host you.