Updated 2025. Do you need a relaxing weekend away with your sweetheart? Luckily, you don’t have to look far to find the best weekend getaway from Washington D.C. Come slip away, just the two of you, and rekindle the romance along Maryland’s Eastern Shore! Just across the Chesapeake Bay, historic Chestertown is the ideal destination for a romantic escape. Here’s what you’ll discover when you visit!
Things to Do in Chestertown, MD
Maryland’s Eastern Shore is full of charming waterfront towns like Easton and St. Michaels, each offering picturesque scenery and delightful experiences. Chestertown is ideal for visitors looking for quieter and less touristy vacation destinations near Washington, D.C. It boasts charming cobblestone streets, fabulous shopping and dining, and a unique atmosphere. Chestertown is a destination like no other – and it’s just a short 1 ½ hour drive from Washington D.C.! Here’s how you can experience your getaway to the fullest:
1. Tour Chestertown’s Historic Sites
Start your weekend in downtown Chestertown! Our town is not only one of the most beautiful and charming towns in the mid-Atlantic but also one of the most historic. Founded in 1706, the town was a flourishing international port during colonial times. Washington, Jefferson, and Patrick Henry, among others, were known to pass through on their way to and from the Continental Congress. During the 1960s Civil Rights Movement, our very own Cannon Street was the site of the Freedom Riders protest against segregation. Now, Chestertown is home to nearly two dozen spots listed on the National Register of Historic Places!
You could easily spend days exploring Chestertown’s many museums, monuments, and historic sites. We highly recommend starting your weekend with a self-guided walking tour of the downtown. As you stroll the cobblestone streets, you’ll see centuries-old monuments and mansions, beautiful architecture, and famous landmarks. To learn more about our local history, make sure to visit the following:
- Washington College
- Sultana Education Foundation
- Chesapeake Bay Maritime Museum
- Harriet Tubman Underground Railroad Byway
2. Browse Unique Shops and Galleries
While you’re downtown, we suggest a little retail therapy. The Eastern Shore of Maryland is known for its one-of-a-kind boutiques, specialty stores, and art galleries. No matter what you’re searching for, you’re sure to find it while shopping in Chestertown.
Browse the local masterpieces at The Artists’ Gallery, find unique gifts at Twigs and Teacups, or enjoy mid-day sips and small bites at Chester River Wine and Cheese Company, And you definitely won’t want to miss the Chestertown Farmers Market in Fountain Park! Open year-round on Saturdays from 8 a.m. until noon, the market offers a great selection of local Maryland produce, baked goods, soaps, plants, and more.
3. Enjoy the Great Outdoors
When was the last time you unplugged? The Eastern Shore of Maryland is the ideal place to reconnect with nature – and each other. Spend a day relaxing by the Chester River, hike miles of scenic trails at Eastern Neck Wildlife Refuge, or stroll the beautiful gardens at Adkins Arboretum (both destinations are about 30 minutes from our Inn). Whether you’re interested in hiking, biking, wildlife viewing, or boating, the possibilities are endless here!
4. Take a Boat Tour on the Chesapeake Bay
Is there anything more romantic than a sunset sail along the Chesapeake Bay? Get ready for the boat tour of a lifetime Blue Crab Chesapeake Sailing Charters! Climb aboard the spacious 43’ Island Girl yacht and enjoy a comfortable cruise along the Chesapeake Bay. As you take in the breathtaking views, Captain Mark and First Mate Suzanne point out all the main points of interest.
If you want to see the fishermen out, dawn and dusks are peak times for fishing activity. A boat tour is the perfect way to start or end your day. Bon voyage!
5. Catch a Show at the Theatre
Chestertown has several excellent entertainment options if you still have energy after your adventures. We highly recommend visiting the Garfield Center for the Arts for those planning weekend trips from D.C. in winter. There is something for everyone, from musicals and comedies to dramas and live music performances! If you prefer to watch a movie, head to Flagship Cinemas for a unique viewing experience. Are you searching for the best live music venues? Look no further than The Mainstay in Rock Hall. This popular entertainment hub is just a short 15-minute drive from Brampton 1860!
Dining in Chestertown, MD
If there’s one thing that Chestertown is known for, it’s mouthwatering coastal cuisine. Tantalize your taste buds with the freshest seafood you will ever taste, including traditional Maryland blue crab, oysters, scallops, rockfish, and more.
Beyond delicious seafood, you’ll also discover an excellent selection of farm-to-table eateries, bayfront restaurants, intimate cafes, wineries and fine dining establishments. Our Eastern Shore, MD restaurants will satisfy any palate, no matter your craving. Try to save room for dessert! See our list of favorite restaurants in Chestertown for an in-depth look at each of our recommended eateries.
Romance the Weekend Away at Brampton 1860
After a fun outdoor adventure, kick back and relax at Brampton 1860. Let yourself be pampered with a single or couples massage in the privacy of your room or cottage at Brampton 1860! It’s the perfect way to relax and unwind during your weekend getaway from Washington, D.C.
Our romantic Maryland bed and breakfast sits on 20 acres of landscaped gardens, meadows, and forests on Maryland’s Eastern Shore. With a serene setting and breathtaking views, it’s the ideal escape for those seeking privacy and comfort.
Start planning the Eastern Shore, Maryland, getaway you deserve! To plan the most romantic getaway from D.C., look no further than our enchanting Maryland bed and breakfast. Brampton 1860 is just a stone’s throw from historic Chestertown and offers the ideal accommodations for a memorable stay. Each of our guest rooms and cottages features top-notch amenities to ensure your stay is comfortable. We also offer two pet-friendly cottages for guests traveling with their four-legged friends!
We can’t wait to welcome you to your best weekend getaway from Washington, D.C. During your weekend at Brampton 1860, you can expect to start each day with a delicious, handcrafted complimentary breakfast. Then, return for afternoon refreshments and tasty appetizers during our Tea Time and Social Hour.
So, what are you waiting for? Check our availability and book your stay today!
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