Here Is the Ultimate Itinerary for 3 Nights in Chestertown, MD

When planning a trip to Chestertown, MD, the hardest decision you’ll have to make is what to do first. This historic waterfront town is brimming with activities, award-winning restaurants, and endless sightseeing opportunities. Many first-time guests ask us for our top recommendations about the best dining, shops, and local attractions. To make vacation planning easier, we’ve put together the following itinerary for 3 nights in Chestertown, MD. Check it out and get ready for an unforgettable getaway to Maryland’s Eastern Shore!

Visiting Chestertown, MD: A 3-Night Itinerary

Day One: Tour the Chesapeake Bay

Check into Brampton Inn and get settled into your guest room or cottage. After you unpack, it’s time to start exploring! 

We recommend taking a Chesapeake Bay boat tour first, as this is one of the best ways to discover the natural beauty of the Eastern Shore of Maryland. While there are several amazing tour services, one of our favorites is Blue Crab Chesapeake Sailing Charters. Climb aboard the 43’ yacht and get ready for a relaxing cruise along the picturesque Chesapeake Bay. With more than 20 years of experience, Captain Mark and First Mate Suzanne are always happy to share their local knowledge with you. Enjoy the beautiful views while you become acquainted with the area.

After your boat tour, stop into 98 Cannon Riverfront Grille for lunch. With beautiful waterfront views and mouthwatering cuisine, Chestertown’s newest restaurant is open every day of the week! Once you’ve finished lunch, enjoy the rest of your afternoon browsing through the shops and galleries downtown. Then, return to Brampton Inn for our afternoon Tea Time and Social Hour. Enjoy an array of sweet treats, appetizers, and refreshments in the dining room. At the end of a perfect day, return to your luxurious accommodations and unwind.

Day Two: Dive Into History

Wake up to a delicious complimentary breakfast at Brampton Inn, complete with fresh juice, handmade pastries, and other homemade specialties like our blueberry pancakes and Eggs Benedict. After breakfast, get ready to explore Chestertown’s historic sites and museums. Learn about Eastern Shore history at Washington College, Sultana Education Foundation, or the Chesapeake Bay Maritime Museum. Then, take a self-guided tour of the Harriet Tubman Underground Railroad Byway. See firsthand where Ms. Tubman lived and helped others find their freedom.

You can easily spend an entire day learning about Chestertown’s rich history and still have so much more to uncover. Break for dinner at Luisa’s Cucina Italiana and fill up on a hearty serving of authentic Italian cuisine. Located in the heart of downtown, Luisa’s dishes are prepared with only the freshest ingredients. From pizza and pasta to seafood and veal, each item on the menu is superb. Afterward, stay out and explore the local nightlife or come kick back and relax at Brampton Inn!

Day Three: Explore the Great Outdoors

Awaken to the smell of freshly-brewed coffee, sizzling bacon, pancakes, and eggs. Enjoy your complimentary breakfast to prepare for another day of adventure. The Eastern Shore of Maryland is a prime destination for outdoor recreation, including boating, hiking, biking, hunting, wildlife viewing, birding, and more. Visit one of the nearby beaches, bike along scenic trails, or tour Crow Vineyard and Winery. Nature-lovers will also want to visit the Adkins Arboretum, Eastern Neck Wildlife Refuge, or the Blackwater National Wildlife Refuge.  

When you start to work up an appetite, stop by Fish Whistle for some classic Maryland crab. This local restaurant prepares crab in almost every way you could imagine, as well as fresh fish, shrimp, oysters, calamari, mussels, scallops, and more. Once you’ve filled up, return to Brampton Inn and take a tour of our gorgeous garden. The Inn sits on 20 beautifully landscaped acres, four of which are listed on the National Register of Historic Places. Come reset in nature and then join us for a glass of wine at Social Hour. It’s the perfect way to end your itinerary for 3 nights in Chestertown, MD.

Day Four: Reminisce on Your Amazing Vacation

Start off your last morning at Brampton Inn with a full complimentary breakfast to send you on your way. As you travel back home, enjoy the fantastic memories you’ve made on your Eastern Shore of Maryland vacation. Then, start thinking about making plans to return soon. We can’t wait to welcome you back!

Book Your Stay at Brampton Inn!

Now that you have your itinerary for 3 nights in Chestertown, MD, it’s time to book your trip! When it comes to accommodations in Chestertown, MD, no place can compare to our romantic bed and breakfast. Brampton Inn’s guest rooms and cottages feature luxurious amenities, ensuring a relaxing stay every time. The spacious rooms inside our 1860 Manor House offer the privacy and comfort you desire. Relax on your King or Queen bed, take a soak in your spa tub or shower, or curl up next to the fireplace during the winter months. 

Poppy's RetreatNestled in the woods, away from the Main House, the cottages offer even more seclusion. Each cottage features wood-burning fireplaces for the colder months and a private bath. Many of them even include unique amenities such as full kitchens, private porches, or whirlpool tubs. For a truly unforgettable stay, we recommend booking Russell’s Cottage. This pet-friendly accommodation features a King bed, fireplace, and an adjoining bath with a deep tub/shower combo and a heated towel bar. It even has a private enclosed garden with a sitting area, making it the ideal choice for a relaxing getaway. Check our availability and book your stay today!

Book Now

Cast Your Vote!


We are honored to announce that Brampton 1860 has been nominated in the “USA Today 10Best Readers’ Choice 2024” awards for the category of “Best Bed and Breakfast”!
Voting is opens July 8 at Noon and runs through Noon on August 14th. Please Share the love by casting your vote daily!
Vote Now