Welcome to the charming town of Chestertown, Maryland, an ideal backdrop for our wedding celebrations. Picture the Eastern Shore with rich history, a vibrant arts scene, and breathtaking views. Enjoy coastal cuisine, explore historic Washington College, and relax in nature’s tranquility. Our Chestertown travel guide highlights local markets featuring artisan crafts and fresh produce, scenic waterfront strolls along the Chester River, water adventures, and historic tours. Don’t miss the local galleries that capture the creative spirit of this delightful town.

What comes to mind when you think of Maryland’s Eastern Shore? For us, it’s the area’s rich history, vibrant arts scene, and stunning landscapes. At the heart of it all lies the enchanting town of Chestertown, a true gem on the Eastern Shore. Here, you can savor fresh coastal cuisine, explore the historic campus of Washington College, and immerse yourself in the beauty of nature. To help you plan your visit, we’ve created a Chestertown travel guide featuring some of our favorite experiences on Maryland’s Eastern Shore:

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

Watershed Alley
Chestertown’s newest restaurant! Enjoy traditional preparations with local ingredients for dishes that are authentic to our Chesapeake origins.

Bad Alfred’s
A brewpub and distillery featuring house-made spirits, local craft beer and wood-fired pizzas. Good food, friendly people.

Cafe Sado
Great food, extensive sushi offering, this is Southeast-style Asian cuisine!

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

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

It’s Masala Time
Experience authentic Indian cuisine with a modern twist. Try something new every time you visit. Open daily!

Luisa’s Cucina Italiana
A little slice of Italy in the heart of historic Chestertown.

Modern Stone Age Kitchen
Artisan food created 100% from scratch using only the finest ingredients. Also offer fun weekly food-making classes!

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

The Retriever Bar & The Decoy Bottle Shop
A bar featuring oysters and other victuals. Not your standard fare and the food never disappoints! Check-out the Decoy Bottle Shop as well for an eclectic selection of beer, wine and spirits.

Stam’s Luncheonette
Chef/owner brings her passion for pastry, cakes, ice cream and staples of classic American fare, creating delicious treats! You must try the homemade ice cream!!

Other Fantastic Restaurants Near Chestertown, MD

Fish Whistle at the Granary (Georgetown)
Waterfront dining on the beautiful Sassafras! Delicious menu, weekly specials and full-service bar.

Deep Blue at Kitty Knight (Georgetown)

Enjoy a hilltop view of the Sassafras while you dine. Indoor and outdoor seating. Open daily.

Blue Heron Oyster House (Rock Hall)
Enjoy great seafood and more in a casual bar setting. Indoor and outdoor dining.

Flying Decoy Bar and Grill (Rock Hall)
Enjoy Eastern Shore Cuisine. Located in the heart of Rock Hall.

Osprey Point Restaurant (Rock Hall)
If you’re looking for a fine dining spot, this is a great option! Perfect for a fancy night out with that special someone.

Waterman’s Crab House at Sharp Street Wharf (Rock Hall)
A casual, waterfront restaurant that serves a variety of seafood. 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.

Great Local Markets

Chestertown Farmers Market
Enjoy the Farmers and Artisans’ Market in downtown Chestertown every Saturday from 8am until Noon.

Chestertown Natural Foods
Features local, all-natural and organic vendors and strives to provide the best gourmet products available.

Cross Street Food and Garden
Offers a hearty mix of local foods, meats, natural foods and groceries, baked goods, produce fruits and vegetables, dairy, and plants. Located in Galena.

Fresh Start Food and Garden
An open-air market that serves local produce, natural foods, gourmet meats and cheeses, and other delicious foods. A hidden gem is their fresh made to order deli and a little spot to sit down and eat. Located in Rock Hall.

Discover the Beauty of Chestertown & Beyond

Chestertown, nestled along Maryland’s Eastern Shore, is a haven for outdoor enthusiasts. Whether you’re into hiking, boating, birdwatching, or simply soaking in nature’s beauty, this charming destination has something for everyone. You are just minutes from the Chester River and Chesapeake Bay and 1 hour 45 minutes from a variety of beaches on the Atlantic coast. Get on the water here and consider a fishing charter to catch rockfish. Whether you’re sailing on the bay, hiking through lush trails, or simply relaxing in nature, Chestertown and its surroundings offer endless opportunities for adventure.

Adkins Arboretum

Immerse yourself in the beauty of this 400-acre native garden and nature preserve.

Betterton Beach

A peaceful, sandy retreat just a 20-minute drive from Brampton—perfect for a quiet beach day.

Eastern Neck National Wildlife Refuge

Discover a 2,300-acre island habitat with scenic nature trails, picnic spots, and diverse wildlife.

Tuckahoe State Park

Explore 20 miles of scenic trails, enjoy flatwater canoeing, or try your hand at fishing and hunting.

Sassafras Natural Resources Management Area

A paradise for hikers, mountain bikers, and nature lovers with scenic trails and wildlife viewing opportunities.

Millington Wildlife Management Area

A 3,800-acre preserve with stocked fishing ponds and rich birdwatching opportunities, including woodpeckers and bald eagles.

On the Water

Blue Crab Sailing Charters

Set sail on the Chesapeake Bay with day trips, sunset cruises, and hands-on sailing instruction. Reservations required.

Chester River Kayak Adventures (Rock Hall, MD)

Paddle through the peaceful tidal waters of the Chesapeake Bay with expert guides. Reservations required.

Chester River Packet Company

Cruise the scenic Chester River aboard a 1920s-style, 65-foot classic yacht. Reservations required.

Historic & Scenic Landmarks

Mount Harmon Plantation

Step back in time at this stunning 18th-century estate featuring a restored manor house, nature trails, and waterfront views.

Birdwatching & Wildlife Viewing

Maryland’s Eastern Shore is home to an incredible variety of bird species, including bald eagles, ospreys, and tundra swans.

Sandy Point State Park

Enjoy fishing, swimming, and breathtaking views of the Chesapeake Bay—an idyllic spot for a romantic picnic.

https://theartistsgalleryctown.com/The Artists’ Gallery
An artist collective that presents a variety of art medium. You’ll find the area’s talented artists who hang their work for all to see.

Diane Rappisi Fine Art
Diane Rappisi is a contemporary realist artist offering her own works as well as classes and multi-day workshops in studio.

Hegland Glass
Offers contemporary kiln-formed art glass.

Massoni Art Gallery
Respected by artists & collectors throughout the Mid-Atlantic for over 30 years.

River Arts Gallery
Offers works by local artists in many mediums with a mission of growing community, creativity and connection through the Arts.

Robert Ortiz Studio
Contemporary furniture in the Shaker and Japanese traditions. Also offers one on one furniture making workshops.

Chestertown Farmers Market
Takes place year-round on Saturdays at Fountain Park from 8 am to noon.

Bee Crafty Collectibles
New, old and vintage collectibles.

Bespoke Chocolate
Offers decadent truffles, bon bons, dipped fruit, cordials and 16 flavors of fudge.  All are hand-made of the freshest ingredients with no preservatives. Yum!

Houston’s Dockside Emporium
Traditional to trendy clothing for women and men, accessories, sterling silver and costume jewelry, gifts, books.

The Finishing Touch
Specializing in in custom framing, fine hart, select gifts, artist’s materials, digital imaging and art reproduction.

The Hickory Stick
If you’re looking for a unique gift, we recommend stopping by.

Twigs and Teacups
A 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.

Walnut & Wool
Vintage and new clothing, furniture and home decor.

Hooked on the River
Provides all that’s needed for a great day of fishing, plus kayaks.

Silver Linings Jewelry
Extensive collections of sterling silver and gemstone jewelry.

Park Row Floats
A premier relaxation experience, including float, suana and salt cave services.

Firehouse Antiques
Located in Galena, full of unique 18th and 19th century treasures. We found some great pieces for the Inn here!

Crow Vineyard and Winery
 Crow is a 365-acre working farm, with winery, tasting room, cattle and horses. Guest can sip wines enjoy light fare and tour the farm and winery to learn about how the Crow’s are making dry style premium wines. This family farm also hosts a variety of events each month.

Godfrey’s Farm
You can get many of fruits & vegetables from this pick-your-own farm.

Lockbriar Farm
Family-owned and operated u-pick fruit farm committed to providing the highest quality of fresh, local products and outdoor fun since 1993.

Wildly Native Flower Farm
A beautiful farm offering fun events from floral arrangement classes to goat yoga.

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.

St. Michaels, MD (1 hour from Chestertown)

This charming, walkable town is steeped in maritime history. Known as the “Town that Fooled the British,” St. Michael’s walkable downtown has a variety of cute shops and eateries. The Inn at Perry’s Cabin is particularly famous as a filming location for “Wedding Crashers.” 

• Chesapeake Bay Maritime Museum: Explore exhibits, historic boats, and a working boatyard. Exhibitions and vessels are devoted to the area’s watermen and maritime history.
• Take a Cruise: Enjoy a scenic boat tour or sailing charter on the Miles River.
• Boutique Shopping & Dining: Discover charming shops and fresh seafood restaurants along Talbot Street.

Ocean City, MD & Delaware Beaches (1 hour 45 minutes from Chestertown)

A classic Maryland beach destination known for sun, sand, and seaside fun. You can also find a variety of beaches on the Maryland and Delaware Coast, including Rehoboth, Bethany, Ocean City, Delaware Seashore State Park, and Assateague. Assateague Island is particularly unique for its wild ponies.

• Ocean City Boardwalk: Stroll the iconic three-mile boardwalk with shops, arcades, and delicious treats like Thrasher’s French Fries.
• Beach Time: Relax on miles of sandy beaches or swim in the Atlantic Ocean.
• Jolly Roger Amusement Park: Enjoy family-friendly rides, mini-golf, and water slides.
• Dining on the Bay: Feast on Maryland crab cakes or enjoy a sunset dinner at Fager’s Island.
• Watersports: Try parasailing, jet skiing, or take a boat tour to see dolphins.

Cambridge, MD (1 hour 45 minutes from Chestertown)

Cambridge is most famous as the birthplace of Harriet Tubman, the key conductor of the Underground Railroad. Visitors can experience Tubman’s story through the road trip known as the Tubman Byway. This self-guided, scenic driving tour includes more than 30 sites, many of them with outdoor markers or interpretive signs that share the story of that place.Highlights include the Harriet Tubman Underground Railroad State Park and Visitor Center, The Harriet Tubman Museum & Educational Center (home of the Harriet Tubman Mural), the Dorchester County Courthouse (with its magnificent, new bronze sculpture honoring Tubman). The byway in Dorchester County also includes the Blackwater National Wildlife Refuge, a major bald eagle nesting area with a cool wildlife drive, walking, and paddling trails.

Annapolis, MD (1 hour from Chestertown)

Maryland’s capital and a charming waterfront city rich in history and maritime heritage. At the heart of this maritime town lies the US Naval Academy, an anchor of naval tradition and education. The Hammond-Harwood House, a house that has stood since the British colonial era, unfolds the state’s colonial and revolutionary history. To truly get a feel for the spirit of this community, you must wander through the Annapolis Historic District, where 18th-century buildings line cobblestone streets and present a glimpse into early American architecture.

• United States Naval Academy: Tour the prestigious campus and visit the Naval Academy Museum.
• Annapolis City Dock: Stroll along the waterfront, watch boats in Ego Alley, and enjoy outdoor dining.
• Historic Downtown: Explore charming streets lined with shops, galleries, and colonial-era architecture.
• Chick & Ruth’s Delly: A local institution famous for crab cakes and giant milkshakes.
• Sail on the Bay: Book a sailboat cruise or rent a kayak to explore the Chesapeake waters.

Rock Hall, MD (20 minutes from Chestertown)

A charming fishing village with beautiful waterfront views.

• Waterman’s Crab House: Feast on steamed crabs with a view of the Chesapeake Bay.
• Rock Hall Beach: A small, peaceful beach perfect for a sunset stroll.
• The Mainstay: Catch a live music performance at this intimate venue.

Oxford, MD (1 hour from Chestertown)

A quaint and quiet waterfront town full of history.

• Oxford-Bellevue Ferry: The nation’s oldest privately operated ferry, offering stunning views across the Tred Avon River.
• The Robert Morris Inn: Dine at this historic inn where James Michener wrote parts of Chesapeake.
• Oxford Waterfront Park: Relax along the scenic waterfront.

Crow Vineyard & Winery (25 minutes from Chestertown)

A must-visit for wine enthusiasts.

• Tastings & Tours: Sample award-winning wines made from local grapes.
• Farm-to-Table Bites: Enjoy light fare paired with your wine.
• Events: Attend wine dinners, live music events, and more.

Washington, D.C. (1.5 hours from Chestertown)

The nation’s capital offers iconic landmarks, world-class museums, and rich history.  Definitely worth a day-trip if you’ve never been. DC has loads of free museums, a world-class (and also free) zoo, and historic landmarks and monuments. 

• National Mall: Visit iconic monuments, including the Lincoln Memorial and Washington Monument.
• Smithsonian Museums: Explore world-class museums, from the National Air and Space Museum to the National Museum of American History (free admission).
• U.S. Capitol: Tour the seat of the U.S. Congress.
• Georgetown: Shop and dine in this historic and picturesque neighborhood.
• Tidal Basin: Walk along the water, especially stunning during the cherry blossom season.

Baltimore, MD (1.5 hours from Chestertown)

A vibrant city known for its waterfront charm, rich history, and delicious seafood. Baltimore’s Inner Harbor  features an amazing aquarium (not free) and some interesting museums as well.

• Inner Harbor: Explore this iconic waterfront area with shops, restaurants, and attractions.
• National Aquarium: Discover marine life from around the world at one of the country’s top aquariums.
• Fell’s Point: Walk the cobblestone streets of this historic neighborhood filled with pubs and waterfront views.
• Fort McHenry: Visit the birthplace of the U.S. national anthem.
• Lexington Market: Enjoy a famous crab cake from Faidley’s Seafood.

Philadelphia, PA (1.5 hours from Chestertown)

The birthplace of America, filled with rich history and iconic landmarks.

• Independence National Historical Park: Visit the Liberty Bell and Independence Hall, where the Declaration of Independence was signed.
• Philadelphia Museum of Art: Explore world-renowned art collections and run up the famous “Rocky Steps.”
• Reading Terminal Market: Indulge in Philly favorites like cheesesteaks, soft pretzels, and Amish baked goods.
• Eastern State Penitentiary: Tour this historic prison known for its haunting architecture.
• Magic Gardens: Discover a vibrant mosaic art installation by Isaiah Zagar.

Brittland Manor offers a picturesque setting for our special day, on the eastern shore of Maryland. Located in Chestertown, a royal port of entry since 1706. The ceremony will take place outdoors, surrounded by the serene beauty of nature. Following the vows, guests will enjoy a tented reception where elegance meets the great outdoors. With its historic charm and stunning landscapes, Brittland Manor is the perfect backdrop for our celebration of love.