8 of the Most Overlooked Towns in Chesapeake Bay

The Chesapeake Bay is known for its spectacular coastal scenery, relaxed atmosphere, and plenty of outdoor activities. As the largest estuary in America, it holds almost 18 trillion gallons of water, with over 18 million people and more than 3,600 plant and animal species calling it home. Several towns have cropped up along the great body of water, taking advantage of its potential as a transportation hub, a source of sustenance, and an area of natural beauty.

From rich maritime history and a large blue crab population to a wide variety of flora and fauna, the region has an interesting heritage worth exploring, and there is no better place to do that than in these small towns in the Chesapeake Bay. While there is no shortage of options to visit on your Chesapeake Bay itinerary, these are some of the most underrated.

St. Michaels, MD

St. Michaels is a quintessential waterfront community in Maryland’s Talbot County, set along the Miles River. Despite its modest population, it boasts a storied heritage from its early days, intertwined with shipbuilding, crabbing, and oystering. The Chesapeake Bay Maritime Museum offers a vivid look into the town’s nautical heritage by displaying a vast collection of artifacts from the region. The Hooper Strait Lighthouse, which dates back to 1879, is a must-visit historical site in the town and a representation of its seafaring significance.

Tourists have numerous opportunities to get on the water for a unique perspective of the town. You can rent a kayak, canoe, or paddle board from Shore Pedal & Paddle to enjoy a laid back trip along the calm waters of the bay and soak in the pristine coastal scenery. St. Michaels is also known for its bustling craft brewery and winery scene, and stopping by St. Michaels Winery offers a taste of various award-winning local wines.

Rock Hall, MD

A combination of awesome boating opportunities, a thriving seafood industry, and a relaxed holiday atmosphere draws visitors to this adorable Maryland small town on the National Chesapeake Scenic Byway. You cannot miss the opportunity to get on the water, especially with numerous local outfitters granting tourists remarkable excursions. Booking a trip with the Blue Crab Chesapeake Sailing Charters delivers 90 minutes of relaxed cruising and the opportunity to witness spectacular sunsets over the horizon. Beachgoers who would fancy a dip in the water can head to Ferry Park, which features a lovely swimming beach without the crowds and a gazebo for those who want to sit back and enjoy the scenery.

For some bit of local heritage, the Waterman’s Museum chronicles the town’s crabbing, oystering, and fishing history as seen in a variety of interesting exhibits. Meanwhile, nature enthusiasts will appreciate the biodiversity of Eastern Neck National Wildlife Refuge, which spans over 2,800 acres on the Chester River-Chesapeake Bay confluence.

Havre De Grace, MD

Havre de Grace lies where the Susquehanna River flows into the Chesapeake Bay, resulting in picturesque natural beauty and plenty of outdoor recreation. Many tourists like to stroll along the Havre de Grace Promenade and enjoy the scenery, featuring exquisite views of the Susquehanna River. Elsewhere, Susquehanna State Park presents a wealth of recreational opportunities, ranging from camping and hiking to fishing and boating. The park has at least 15 miles of marked trails and houses notable historical sites, including the Rock Run grist mill.

An impressive mix of museums across the town makes Havre de Grace an interesting stop for history buffs. At the Havre de Grace Maritime Museum, guests get an interesting glimpse into the nautical heritage of the Chesapeake Bay and the Susquehanna River. Meanwhile, the Havre de Grace Decoy Museum hosts one of the country’s finest collections of duck decoys, dedicated to the local duck hunting industry.

Chestertown, MD

This charming port town on the head of the Chester River stands out for its lively art scene and rich history. Its historic district boasts over a dozen sites listed on the National Register of Historic Places. Travelers can explore more about this heritage inside the Historical Society of Kent County, which exhibits a cluster of documents, artifacts, and archives sourced from around the region. Art enthusiasts should expect a busy day in Chestertown, thanks to its rich collection of visual and performing art centers. One of the best stops in town is the Garfield Center for the Arts, which entertains the public with live plays, drama, and musical shows.

Those who want to savor the beauty of the open spaces can charter a cruise with the Chester River Packet Company, which takes tourists on a laidback excursion along the river in a 1920s-style tour vessel. Finally, one of the best ways to interact with the local community is to shop at Chestertown Farmers Market, where friendly faces and wide smiles make for unforgettable encounters.

Easton, MD

Easton is one of the best towns in Chesapeake Bay to visit for arts and culture enthusiasts. This small community in Talbot County impresses with several visual and performing art centers, highlighted by the Academy Art Museum, which houses diverse art exhibits and stages moving theatrical performances as a way to support the local industry. Beyond the rich art scene, outdoor enthusiasts can take advantage of diverse recreational opportunities at Idlewild Park, home to amenities like a playground, picnic areas, tennis courts, and a walking trail.

On the other hand, those looking for some fun at sea can head to East Point Marina and charter a boat to explore the town from the water. Also, be sure to immerse in an exciting cultural experience by shopping at the Amish Country Farmers’ Market, where delicious home-baked goods, handcrafted souvenirs, and other Amish-made merchandise abound.

Cape Charles, VA

Cape Charles traces its beginnings back to 1883 and stands out for its historic district hosting the largest concentration of historical buildings on the East Coast of the United States. Strolling through the neighborhood exposes a collection of art galleries, museums, ice cream shops, and restaurants housed in 19th-century buildings, with several listed on the National Register of Historic Places. The Ellen Moore Gallery offers a hint of the local art scene by allowing visitors to peruse a diverse collection of pieces by local, regional, and national creators.

Outdoor recreations abound inside the sprawling Cape Charles Natural Area Preserve, which harbors a mix of habitats, featuring a maritime forest, coastal beach, and dunes. A long boardwalk through the forest allows you to explore the area on a relaxed stroll while soaking in spectacular views of the water. When peckish, be sure to sample the delectable seafood scene in Cape Charles at The Shanty.

Irvington, VA

Irvington’s claim to fame is home to the nationally renowned The Tides Inn, a timeless waterfront hotel with an easygoing setting and breathtaking views of the Rappahannock River. This is an excellent place to book a room for your night stay before starting to explore the town. Several historical markers will attract your attention in Irvington, most notably the Steamboat Era Museum. This remarkable facility tells the story of steamboats along the Chesapeake Bay, and how their advent changed the lives of the people in the area as a form of economic lifeline.

A notable appreciation for the arts is evidenced by several art venues in the town, including Objects Art and More. Housed inside is a world-class collection of paintings, furniture, sculptures, jewelry, pottery, and other unique treasures, promising to intrigue any connoisseurs in Irvington. Vacationing families will have a fun time at the Compass Entertainment Complex, with activities like miniature golf, bumper cars, go-karts, and wall climbing tailored to all ages.

Cambridge, MD

Rich maritime heritage and unique Eastern Shore traditions come to a head in this quaint Dorchester County town, presenting visitors with a walkable and boatable holiday destination. A treasure trove of historical markers offers an interesting glimpse into local history. Notable mentions include the Harriet Tubman Museum and Educational Center, which pays tribute to the legendary slavery-era heroine. The Richardson Maritime Museum is another must-visit if you want to explore almost three centuries of nautical heritage in the region, portrayed through antique vessels and other exhibits.

Outdoorsy travelers will prefer visiting Long Wharf Park, which provides a relaxed atmosphere that is perfect for relaxing along the Choptank River. While strolling along the secluded trails in the area, you will come across the Choptank River Lighthouse, a famous town landmark and a popular subject for photographers in Cambridge.

America’s Eastern Shore presents a selection of laidback locations that will make for the ideal holiday escape. These charming towns in the Chesapeake Bay invite tourists to experience the beauty of the famous waterbody and learn about the communities that have called it home through the centuries. With rich maritime history, exciting water-based adventures, sumptuous seafood culture, and unique local traditions to explore, they make for an unforgettable vacation destination tailored for all types of travelers, whether outdoor enthusiasts, culture vultures, or history lovers.