3 Reasons Chestertown Is One of the Best Weekend Getaways From Baltimore

Sometimes, all it takes is a weekend escape to rekindle that spark in your relationship. If you need some time alone with your sweetie, why not plan a romantic getaway to Maryland’s Eastern Shore? Come stroll the charming streets of Chestertown, set sail along the Chesapeake Bay, or explore the area’s rich history and cultural offerings. At the end of each blissful day, unwind in luxurious accommodations at Brampton Inn. Are you ready to experience one of the best weekend getaways from Baltimore? 

How Far Is it From Baltimore to Chestertown, MD? 

When considering last-minute getaways from Baltimore, MD, Chestertown should be at the top of your list! It only takes 1 ½ hours to drive here from Baltimore. The best way to get to Chestertown is to go South over the Chesapeake Bay Bridge. You can also drive around the bay via I-95 North and MD 213 South. This northern route via Elkton is equally as scenic and just adds 20 minutes to your trip. 

Top 3 Reasons to Plan a Weekend Getaway to Chestertown, MD


1. Reset in Nature

The Eastern Shore of Maryland offers a peaceful respite from the hustle and bustle of city life. Here, you’ll discover stunning natural beauty, shimmering waters, and lush forests. Take your sweetheart on a boat tour of the Chester River or the Chesapeake Bay. Enjoy the magnificent views while you glide off into the sunset. Are you up for more of a challenge? Get out and explore miles of hiking trails at Blackwater National Wildlife Refuge. The Eastern Shore Wildlife Refuge, Adkins Arboretum, or Millington WMA also offer plenty of opportunities for hiking and wildlife-viewing. Afterwards, come explore the beautiful gardens right here at Brampton Inn.

The Eastern Shore of Maryland is also one of the best weekend trips from Baltimore in winter. Enjoy snowshoeing and cross-country skiing through dazzling, snowy landscapes. Or, visit the Eastern Neck Wildlife Refuge and see the Tundra Swans make their appearance from mid-November through March. After a fabulous day exploring winter wonderland, come warm up beside the fire at our romantic bed and breakfast. 

2. Indulge in Delicious Cuisine

Whether you’re craving classic Maryland seafood or farm-to-table eats, Chestertown restaurants will satisfy any palate. Enjoy some of the freshest seafood you will ever taste, dine beside the water, or have a date night in with our homemade Chili Dinner For Two. Chestertown is especially known for blue crab, a Mid-Atlantic staple, so make sure to try some while you’re in town. From intimate cafes and bistros to fine dining establishments, you’ll find a little bit of everything in Chestertown. 

And cooking is our bread and butter here at Brampton Inn! During your stay, you can expect to start each morning right with a delicious, complimentary breakfast. Enjoy fresh, flaky pastries, pancakes, bacon, eggs your way, and much more. We’ll gladly deliver breakfast right to your doorstep if you request it! In the afternoons, come back to the inn for our Tea Time and Social Hour. All of our savories and sweets are freshly prepared each day using local, seasonal ingredients.

3. Explore Art and History

Calling all art enthusiasts and history buffs! If you’re interested in touring museums and art galleries during your getaway, you’re in luck! The Eastern Shore of Maryland is filled with opportunities to explore the arts and learn more about our nation’s history. In Chestertown’s Historic District, you’ll find a wide range of museums and historic sites. In fact, the town has nearly two dozen spots listed on the National Register of Historic Places. You can take a self-guided walking tour and see them all during your visit! We also recommend visiting Washington College and the Harriet Tubman Underground Railroad Byway. 

Those who prefer to explore the arts scene will discover plenty of galleries throughout Chestertown. Take your time browsing local masterpieces at RiverArts, MassiniArt or the Create Galleries. Whether you’re searching for fine art, paintings, textiles, jewelry, pottery, prints, sculptures, you’ll find it all in Chestertown. 

Enjoy Each Day and Romance the Nights Away at Brampton Inn

Now that you’re ready to experience one of the best weekend getaways from Baltimore, it’s time to start planning your trip. When it comes to accommodations near Chestertown, no place compares to Brampton Inn. Our romantic Eastern Shore of Maryland bed and breakfast offers the ideal accommodations for a memorable stay. Each of our rooms and cottages are designed with your ultimate comfort and privacy in mind. We also offer pet-friendly cottages for guests traveling with their four-legged friends.

Brampton Inn is conveniently located near all of Chestertown’s best attractions, but you don’t even have to leave your room if you don’t wait to! Enhance your getaway when you book one of our specials or packages. Let yourself be pampered with a single or couple’s massage right in your room. Or, surprise your sweetheart with roses, chocolate, and champagne waiting for you upon arrival. Check our availability and book your stay today. We can’t wait to welcome you!

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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.

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