couple at romantic Chestertown inn
Things to Do in Chestertown

Spend Time Together Relaxing on the Eastern Shore of Maryland

When you imagine the Eastern Shore of Maryland, what comes to mind? We think of the area’s rich history, thriving arts scene, and breathtaking views. The charming town of Chestertown, MD, is a gem nestled in the heart of the Eastern Shore. Spend your days here tasting delicious coastal cuisine, touring Washington College, and relaxing in nature. Below, we’ve compiled a Chestertown travel guide with a few of our favorite things to do on Maryland’s Eastern Shore:

Share magical moments with each other, whether you’re exploring
our 35 acres or the greater Eastern Shore in Maryland.

Shopping, Art & Farms

Discover Beautiful Things in Our Local Boutiques, Museums & Galleries

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.

picking blackberries in Maryland
charming downtown Chestertown, MD

The Artists’ Gallery
An artist collective that presents a variety of mediums in the heart of town.

Chestertown Farmers Market
In Fountain Park, takes place year-round on Saturdays from 8 am to noon.

You’ll find the area’s most talented artists hang their work for all to see.

Twigs and Teacups
Our favorite gift store in town – smart, small gifts, toys, candles & soaps.

Mimi’s Closet
Discover your new favorite outfit at this clothing and gift store.

The Bookplate
Find (gently) used books at this must-visit gem in the center of town!

Chester River Wine and Cheese Co.
This charming shop supplies us with our cheeses, patés, and fine wines.

Godfrey’s Farm
We get several of our fruits & vegetables from this pick-your-own farm.

The Town of Rock Hall
Gift shops, antique stores, galleries, artisan studios, restaurants & more.

Prime Outlets in Queenstown
Find some deals and delightful shopping at 45 brand name outlet stores.

Dixon’s Auction Sale and Farmers Market
Year-round auction every Wednesday from 9 a.m. to 5 p.m.

Area Events & Festivals

Plan Your Stay Around the Best Events on the Eastern Shore of Maryland

Beautiful scenery, charming mom-and-pop shops, and a vibrant coastal culture are just some of the reasons why the Eastern Shore of Maryland is the perfect year-round destination. Throughout the year there are also fun events to celebrate, and we’ve listed some of the best events on the Eastern Shore of Maryland below!

live music playing guitar and drums

Summer Events

Pirates & Wenches Fantasy Weekend
Held just a short drive away from Brampton Inn (in Rock Hall), this fun festival offers immersive fun for everyone. Buccaneers and land-lubbers will rejoice in this themed, town-wide party every August.

Cars on High
Every 3rd Thursday admire classic, exotic, antique and customized cars are on displayed on the 300 block of High Street. Come Food trucks, too! Cars on High will continue on the third Thursday of the month, weather permitting, through October.

Fall Events

Chestertown Jazz Festival
If you’ve ever visited the Eastern Shore before, you know that it’s a hotbed for all kinds of musical talent! Jazz is an especially prominent genre here. Celebrate this colorful art form at Wilmer Park which showcases a variety of new and established artists.

Sultana Downrigging Weekend
This “tall ship and wooden boat festival” is so much more than meets the eye. Hobbyists love experiencing these stunning vessels in person, but this event also features live music, Dock Dogs competitions, and fireworks.

Jigsaw Puzzle Contests at Brampton Inn
We’re huge fans of Artifact Wooden Puzzles! What began as an addicting hobby for us became something our guests fell in love with, too. In November, grab a partner, and put your skills to the test. You could win a brand new Artifact puzzle of your own.

Annual Chestertown Antiques Show and Sale
Score a valuable, one-of-a-kind piece for your home! The best part about it? Proceeds benefit the Kent Association of Riding Therapy.

Winter Events

A Dickens of a Christmas
Always the first weekend in December. Join the town for a weekend of festivities starting with a special First Friday throughout the Historic District. You’ll find carriage rides, hot beverages, fire pits, s’mores stations, and special entertainment.

Oyster Weekends at Brampton Inn
Oyster season is big here on Maryland’s Eastern Shore. Enjoy complimentary oysters on the half-shell and a glass of bubbly (for guests)! Be sure to check it out on Saturdays at our Tea Time and Social Hour.

Be My Valentine in February!
Come celebrate at the Brampton. A red rose and four house made chocolate truffles will be waiting for you and your Sweetie upon arrival. There will be Chocolate desserts every day in February.

FeBREWary in Maryland
This month, you’ll find several fun beer-themed events on tap across the state. Keep an eye out for Patriot Acre Farm Brewery and Bull and Goat Brewery right here in our neck of the woods!

Spring Events

Jigsaw Puzzle Contests at Brampton Inn
We’re huge fans of Artifact Wooden Puzzles! What began as an addicting hobby for us became something our guests fell in love with, too. In March, grab a partner, and put your skills to the test. You could win a brand new Artifact puzzle of your own.

Chestertown Tea Party Festival
Memorial Day Weekend, this celebration of the town’s Revolutionary War history has a street party atmosphere—there’s food, drink, live music, vendors, and even a crazy raft race! Be sure to mark your calendar for this one.

National Music Festival
For two weeks each June, musicians present over 35 concerts. Renowned classical musician and commentator Miles Hoffman usually makes an appearance!

Outdoor Activities

Experience the Great Outdoors With These Eastern Shore of Maryland Activities

Chestertown is an unforgettable destination along the Eastern Shore of Maryland. The area is home to countless outdoor activities, making it the ideal place for wildlife viewing, hiking, boating, hunting, and more. As a guest of Brampton Inn, you are just minutes away from the Chester River and the Chesapeake Bay. It’s the ultimate setting for your next romantic getaway. Spending an afternoon in the great outdoors is one of our favorite things to do in Chestertown, MD.

couple hiking with dog in Chestertown, MD
Seawall with birds in Chesapeake Bay

Brampton Inn Gardens
The inn sits on 35 intricately landscaped acres, four of which are listed on the National Register of Historic Places.

Adkins Arboretum
Explore the 400-acre native garden and preserve on the Eastern Shore.

Eastern Neck Wildlife Refuge
2,300-acre island habitat with nature trails, picnic areas & wildlife.

Sassafras NRMA
Excellent hiking, mountain biking, wildlife viewing & equestrian trails.

Millington Wildlife Management Area
3,800-acre preserve with four ponds stocked with bass and bluegill. Observe woodpeckers, woodcocks, tanagers and beavers.

Our area is home to hundreds of bird species. Bald eagles, osprey, Tundra swans, Canada geese, and Snow geese are just a few of the region’s most recognizable visitors. The National Wildlife Federation named the Brampton Inn a Certified Wildlife Habitat, making it an excellent spot to watch some of your favorite fliers.

Sandy Point State Park
Spend the day fishing, swimming or wildlife viewing while soaking up stunning views of the Chesapeake Bay. A picnic at Sandy Point is one of the top romantic things to do in Annapolis, MD.

Local Restaurants

These Chestertown, MD, Restaurants Will Make Your Mouth Water

Brampton Inn is the perfect place to experience the Eastern Shore’s homegrown culinary scene, and not just at our complimentary breakfast and tea time. Whether you prefer country favorites, fantastic seafood, or light, farm-to-table bites, you’ll find exactly what you’re craving on the Eastern Shore of Maryland. Our guests love the region’s bayfront eateries, intimate cafes, and fine dining spots. It’s time you experienced it for yourself! We’ve compiled just a few of our favorite restaurants in Chestertown, MD.

plate with gourmet bruschetta and soup

Our Favorite Restaurants in Chestertown, MD

The Kitchen at the Imperial Hotel
This spot offers exceptional food! We partner with them when we do our wine pairing dinners for guests.

Casa Carmen
An innkeeper favorite, this delightful place to eat offers tapas (small plates) and their own wonderful wines!

Luisa’s Cucina Italiana
A little slice of Italy in the heart of historic Chestertown. This restaurant and pizzeria is open every day of the week.

Evergrain Bread Company
A fantastic European-style bakery serving light lunches, sweet treats, and delicious espresso.

98 Cannon Riverfront Grille
Chestertown’s newest restaurant! Enjoy beautiful waterfront views and very good food. Open every day of the week.

Play It Again Sam’s
Enjoy coffee-house vibes and light lunch options. This is one of our favorite spots to chat about town happenings!

Uncle Charlie’s Bistro 
This spot offers an upscale menu with a little bit of everything! It’s open every day for lunch and dinner.

Other Fantastic Restaurants Near Chestertown, MD

Barbara’s on the Bay (Betterton)
You’ll be met with plenty of classic comfort food and spirits. We recommend grabbing a seat on the deck—this spot offers exceptional views of the Sassafras River!

Osprey Point Restaurant (Rock Hall)
If you’re looking for a fine dining spot, this is a great option! The food is a bit pricey, but perfect for a fancy night out with that special someone. Osprey Point is closed Mondays, Tuesdays, and for the entire month of January.

Waterman’s Crab House at Sharp Street Wharf (Rock Hall)
A casual, waterfront restaurant that serves a variety of scrumptious seafood and offers live music on weekends. This is the only restaurant in our area offering steamed crabs in the summer! Keep in mind that this eatery is closed during the winter months.