The Eastern Shore of Maryland means something different to everyone. No one can deny, however, that it’s a place with a thriving art scene and plenty of spots to enjoy some retail therapy! Below, we’ve listed some of the best places to experience these two aspects of Maryland’s Eastern Shore.

For even more local suggestions, don’t forget to view our complimentary Travel Guide! This local resource is packed with all of our favorite places and spaces. Access it today and look forward to experiencing the Eastern Shore of Maryland like a local!

Find Your Favorites

The Artists’ Gallery 

The Artists’ Gallery is an artist collective that presents a variety of mediums. Find The Artists’ Gallery at 239 High Street in the heart of downtown Chestertown.

Chestertown Farmers Market

You won’t want to miss the Chestertown Farmers Market in Fountain Park! the market takes place year-round on Saturdays from 8 a.m. until noon. This is your chance to score local Maryland produce, baked goods, soaps, plants, and more! Everything at the market is local, so you can feel good about your purchases.


CREATE is the newest gallery in the heart of Chestertown’s arts and entertainment district. At CREATE, some of the area’s most talented artists hang their work for all to see. Find this unique spot at 113 South Cross Street!

Twigs and Teacups

Twigs and Teacups is our favorite gift store in town. They offer the best selection of smart, small gifts, kids’ toys, candles, and soaps. We love shopping at 111 South Cross Street!

Mimi’s Closet

Mimi’s Closet is a sophisticated clothing and gift store in the center of town. Discover your new favorite outfit at 307 High Street downtown.

The Bookplate

The Bookplate is one of the best places to find (gently) used books. Many of our returning guests make a point to visit this gem in the center of town! Find The Bookplate at 112 South Cross Street.

Chester River Wine and Cheese Co.

We love Chester River Wine and Cheese Co.! This charming shop supplies us with our cheeses, patés, and fine wines. Head down to 117 South Cross Street and see why we love it!

Godfrey’s Farm

We source several of our fruits and vegetables from Godfrey’s, one of the area’s best local farms. It’s a pick-your-own place, which can make for a fun outdoor experience. Godrey’s Farm is located at 302 Leager Road in Sudlersville, Maryland. They are open from Memorial Day to Labor Day.

Rock Hall

Located just 12 miles away from Brampton Inn, you’ll find the town of Rock Hall. The stores in this charming town include gift shops, antique stores, art galleries, artisan studios, and much more. Go check it out! If hunger strikes, be sure to also check out Rock Hall’s selection of restaurants.

Prime Outlets in Queenstown

Over 45 brand name outlet stores (including Adidas, Banana Republic, Nautica, and J. Crew) can be found at the Prime Outlets in Queenstown. If you’re in need of some new wardrobe pieces, stop by when you’re in town!

Dixon’s Auction Sale and Farmers Market

Dixon’s is a year-round auction offering thousands of items up for bid. You’ll find antiques, furniture, glassware, and other treasures here! The auction happens every Wednesday from 9 a.m. to 5 p.m.

End Your Perfect Day at Brampton Inn!

After a day filled with fun and fancy-free finds, come back to comfort and hospitality at Brampton Inn! Whether you’re searching for a Maryland masterpiece or a beautiful new blouse, Brampton Inn is your perfect home-away-from-home. The Eastern Shore of Maryland isn’t called “The Land of Pleasant Living” for nothing! Our area is characterized by winding country roads, unique shops, plenty of rich history, and delicious coastal cuisine. No matter what brings you to the Eastern Shore, you’ll love relaxing in your bright, airy, and spacious accommodation at Brampton Inn.

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