8 Most Charming Towns Along The Chesapeake Bay

The Chesapeake Bay is a nation renowned destination in the water-bounding reaches of Virginia and Maryland. The shores are dotted with charming towns and villages, home to friendly locals and quaint living atmospheres, with vibrant activities available around the bay. These eight towns along the Chesapeake Bay offer perfect sea-scape that charms from the first glance and pulls one in for life-long memories.

Chesapeake City, Maryland

View of Chesapeake City from the Chesapeake City Bridge, Maryland.
View of Chesapeake City from the Chesapeake City Bridge, Maryland

The town with a big name comes with a whole vacation-worth of activities to charm all of one's senses on a getaway from the real city. One can start experiencing all the scenic town has to offer by waking up with a view at one of the charming bed and breakfasts lining the waterfront. Watching boats dock and depart along the scenic Chesapeake & Delaware Canal is the most scenically-relaxing pastime in-town. The marvelous historic district is lined with local boutiques and antique stores to peruse on an evening stroll.

Chesapeake City Bridge at Sunset, Maryland USA, Chesapeake City, Maryland
Chesapeake City Bridge at Sunset in Maryland

The town's third busiest shipping canal in the world is strewn with colonial- and Victorian-style homes, back from the town's origin in the 19th century. Following a stroll-along the unique storefronts, the C&D Canal Museum awaits with a story about the canal from birth to its present-day role. There are fantastic restaurants to feast on fresh and sustainable seafood like crab dip and calamari, while the Schaefer’s Canal House boasts a dock-terrace for margaritas and live music to sunset sights.

Chincoteague Island, Virginia

View of the Chincoteague Bay Waterfront, in Chincoteague Island, Virginia

This tiny fishing town is the nation-renowned destination for most-charming wildlife sightings. It is home to herds of wild horses roaming the shores of the Atlantic Ocean. One might remember the scenery from the famous novel and film, Misty of Chincoteague. The town comprises a perfect getaway to a remote beach-setting in the surrounding wilderness.

Aerial view of the Long Bridge to Chincoteague Island in Virginia. Reserve with a wide variety of birds and wild horses.
Aerial view of the Long Bridge to Chincoteague Island in Virginia

For relaxing pastimes, there's a wildlife refuge and activities along the national seashore, like fishing, sunbathing, bird-watching, and going for a breezy bike ride. The next-door Wallops Island is home to the NASA Wallops Visitor Center with rocket-launches.

Easton, Maryland

The intersection of Dover and Washington Streets, in Easton, Maryland.
The intersection of Dover and Washington Streets, in Easton, Maryland

The charming town on the Eastern Shore with 14,000-some residents was built around a courthouse. It is a laid-back destination on a getaway to Ocean City, with a walkable downtown area aligned by trees and original Victorian-style architecture. Small Easton boasts immense arts and culture scene, like the annual Waterfowl Festival. It celebrates the Eastern Shore culture through wildlife art, heritage sights, and conservation insights.

EASTON, MARYLAND - CIRCA 1990's: Main Street, Easton, Maryland
Main Street, Easton, Maryland

The Adkins Arboretum comprises a wonderful pastime over a relaxing stroll through the immense fresh-air scenery. It is a 400-acre native garden and preserve inclusive with a water-view to set picnic. The rich cultural spirit extends into the varied cuisine options to choose, from pub food to fine Italian dining, housed in quaint little restaurants. There are tons of unique stores, and antique shopping for new home decor, memorabilia, and souvenirs for others.

Havre de Grace, Maryland

Aerial sunset panorama of Havre de Grace Maryland with orange sky and clouds reflecting on the Susquehanna River and the Chesapeake Bay one of the best small towns in America
Aerial sunset panorama of Havre de Grace, Maryland, with orange sky and clouds reflecting on the Susquehanna River

Havre de Grace is situated at the bay's northernmost tip and named after a French seaport. The charming town with a ring of romance in its name, boasts big personality. There are days-worth of explorations, starting at the Bay. One must visit the bay's oldest lighthouse with amazing views of the Chesapeake Bay, stroll the perfect marina, and watch the sunset from the fishing pier.

Havre de Grace, MD, USA – August 13, 2022: A large sign at the Concord Point Lighthouse at the edge of the Chesapeake Bay shore.
A large sign at the Concord Point Lighthouse at the edge of the Chesapeake Bay shore in Havre de Grace

The active can hike along the state park's 15 miles of wildlife trails, or play a few rounds at the nationally-ranked golf course. The promenade of the town's historic downtown area is great for an atmospheric and relaxing evening-full of great shopping and dining. Havre de Grace is also the quirky "duck decoy capital of the world," with a kitsch museum boasting 3,000 ducks on display.

Kent Island, Maryland

Kent Island, Maryland, Chesapeake Bay water view in Autumn on a beautiful sunny day with blue skies.
Kent Island, Maryland, Chesapeake Bay water view in Autumn on a beautiful sunny day with blue skies.

The largest island on the Chesapeake Bay was the site of Maryland's first European settlement in 1631. It is celebrated in the small town of Stevensville with an annual Kent Island Day in May. There is a parade, exhibits, and other fun discoveries of heritage and modern life on the bay. Today, the island is a galore of activities, including golf, water-sports, and the highlight, seven-mile Cross Island Trail trail to the Kent Narrows Waterfront district. 

View of the bay with marina, waterfront, large parking for yachts and cars on Kent Island in Virginia.
View of the bay with marina, waterfront, large parking for yachts and cars on Kent Island in Virginia

The paved and ADA accessible trail comprises the most popular pastime for locals and destination for tourists. It starts from the Terrapin Nature Park on the scenic shores of the Chesapeake Bay, with running, walking, or cycling through unique views. The environmentally sensitive setting of wildlife, waterfront, and canopied woodland, also gives access to public parks. For a relaxing time into the evening, there are great art galleries and sunset dining at waterfront seafood restaurants. 

Onancock, Virginia

The town hall and police department in Onancock are housed in the town's historic fire hall.
The town hall and police department in Onancock are housed in the town's historic fire hall, via Wikipedia

Onancock is a real charmer, dubbed the “gem of the Eastern shore” by Captain John Smith in the 1600s. The town with a wistful name and tiny population of some 1,500 residents is beloved for budget travels with lots to see and experience. Onancock's small-town appeal envelops world-class amenities, a thriving arts scene, museums, and restaurants for any taste and style. The cultured will love Bay-inspired works by nationally renowned artists, along with catching a screening at the old-school Roseland Theatre.

The bay and yachts in Onancock
The bay and yachts in Onancock

For dining, there's the Bizzotto’s Gallery-Café serving dishes with an Argentinian-Italian flair, or the Irish-scene at the Blarney Stone Pub. The seafood galore of the Mallard’s at the Wharf comes inclusive with serenades from the musically-gifted chef, Johnny Mo. The active drink aficionados will love kayaking to a local winery. Onancock was named “The Coolest Town in the South” for delivering a relaxing experience within authentic Eastern Shore atmosphere. 

Solomons, Maryland

Vintage sailboat in Solomons Maryland
Vintage sailboat in Solomons, Maryland

There's so much to sight and experience in the charming village of Southern Maryland, starting with a great boardwalk. It is wonderful for morning and evening waterfront strolls, perusing many shops and sitting down for a delicious meal within scenery. Families love visiting the Calvert Marine Museum, followed by some fun bonding at the beach, like collecting fossils strewing the shore around the museum.

Calvert Marine Museum Lighthouse
Calvert Marine Museum Lighthouse

For the most scenically-rewarding pastime, there is the forested sculpture park, Annmarie Sculpture Garden & Arts Center. The Smithsonian-affiliated establishment is great for fresh air strolls, and viewing the works of world-renowned artists. The waterside town is also home to local lighthouses, such as one of the few remaining “screwpile” lighthouses on the Bay.

St. Michaels, Maryland

Autumn Color the Chesapeake Bay Shore and Harbor in St Michaels Maryland
Autumn colors at the Chesapeake Bay Shore and Harbor in St Michaels Maryland

The tiny town with a grand personality was founded on the Eastern Shore in the 1600s. The thriving seaport of the past boasts a lively marina with a historic cat-boat Selina II ready to depart on a scenic cruise around the bay. The quintessential town is an ideal Chesapeake destination for families, home to a world-class museum and charming main street with art galleries, luxury hotels and historic inns. The Chesapeake Bay Maritime Museum boasts an 18-acre waterfront-spread of interactive exhibits, boat rides, demonstrations, and other cultural activities around the bay.

Chesapeake Bay with boats St Michaels Maryland USA
Chesapeake Bay with boats in St. Michaels, Maryland

St. Michael's bustling downtown area is chockfull with varied boutiques to stock-up on gifts and great home-finds like artisanal olive oil and antiques. Following a shopping spree, the restaurants galore awaits with trendy tapas bars and casual waterfront dining such as the amazing seafood joint with over 30 beers on tap. The 208 Talbot features a cozy atmosphere to dine on Chef David Clark's famed baked oysters, topped by prosciutto, pistachio, and champagne cream. There is also a winery, brewery, and distillery, with local-favorite, the Carpenter Street Saloon, as well as cocktail cruises.

From former fishing villages to thriving ports, these towns brought historical charm into present-day with marina activities, seafood galore, and atmospheric scenery. The Eastern Shore towns are easily accessible from two states for an ideal destination-getaway suited to any group. The Chesapeake Bay comes with myriad water-bound fun and relaxation, sunset views, and waterfront dining.

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