The Ultimate Summer Bucket List for Your Maryland Vacation

With summer fast approaching, we know your search for a sunny, relaxing getaway is underway. Look no further than Chestertown, for the perfect summer vacation in Maryland at the charming and serene Brampton Inn. Enjoy four dreamy days lounging at the beach, shopping at unique stores, gazing at picturesque landscapes, and tasting fine wines. Keep reading for a specially curated itinerary that ensures endless fun for you and your travel partner. Pack your shades and sense of adventure, the rest is taken care of!

Couple on the beach on a vacation in Maryland

Day One: Soak Up the Sun

After a restful night’s sleep, wake up in your charming cottage or suite and get ready to spend the day at the beach or at the picturesque haven-like Betterton Beach. The Chesapeake Bay sets a stunning backdrop for sunbathing, taking in beautiful views, and exploring the sparkling seas. Whether you’re up for swimming, boating, birding, or simply walking along the sand, you’re sure to enjoy your time outside. When you’ve worked up an appetite, head to one of the fabulous nearby restaurants we love and get a taste for what Chestertown has to offer.

Couple walking down the sidewalk while shopping in Maryland

Day Two: Shop ‘Til You Drop

After a hot cup of coffee and a delicious complimentary breakfast, head downtown to visit unique shops and peruse local art galleries. Start by admiring the work at The Artists’ Gallery and fuel your appreciation for creativity with fresh inspiration. Then stroll through some of Chestertown’s stores that pique your interest to purchase a new book to read during your vacation, a souvenir to take home, or hunt down a special treasure at the Dixon’s Auction Sale and Farmers Market. There’s truly something for everyone!

Couple on a hike while on a vacation in Maryland

Day Three: Explore the Great Outdoors

It would be a shame to let your Maryland vacation come and go without some dedicated time immersing yourself in nature. Get out and explore the great outdoors with an energizing hike on one of our recommended trails or enjoy some time admiring the gardens and gorgeous landscaping that blankets our own 35 acres. For more fun in the sun, set sail with our curated Sailing Package and enjoy a romantic cruise and delicious dinner. After a long fulfilling day, you can retreat back to your home away from home for another peaceful night at our luxurious bed and breakfast.

Couples facial massage on Maryland getaway

Day Four: Sip, Savor & Luxuriate

While your fourth and final day at Brampton Inn may be bittersweet, make it one to remember. Spend the day together unwinding with a relaxing in-room massage by our preferred Massage Orbit provider or ask us for more recommendations. Then meander over to Crow Vineyard and Winery where you can become a wine connoisseur and delight in tastings and a romantic dinner for two back at the Inn. If you’d rather stay close to home you can sip and savor in the comfort of your room while watching the sun set on your last day at our historic inn.

Four-poster bed and fireplace at Maryland bed and breakfast

Plan Your Four-Day Stay

Now that we’ve laid out your itinerary for the perfect vacation in Maryland, all that’s left to do is choose which lodging option you prefer (choose a pet-friendly accommodation if you’re bringing along your faithful pooch) and get ready to enjoy the sun, shops, sips, and more that await in Chestertown. Snag your preferred dates and look forward to starting your own adventure this season. We can’t wait to host you!

If you have time and want to explore further, we would recommend a day trip to St. Michaels!

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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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