9 of The Friendliest Towns In Chesapeake Bay
People flock to the Chesapeake Bay from all across the world, and for good reason. Chesapeake is the largest estuary in the nation where waters from inland rivers meet with the Atlantic Ocean and where vacationers have met with relaxation and fun for years. Its glimmering surface is a jewel in the Mid-Atlantic which is known for its world-class fishing and astounding natural beauty. These nine towns found on the Chesepeake Bay are perfect for exploring its natural beauty, amazing seafood and their hospitality.
Cambridge, Maryland
Found on the state’s Eastern Shore in 1684, Cambridge is known as one of the oldest colonial cities in Maryland. This charming town has a grand maritime heritage as a seaport community built on the Choptank River which can be explored through the town’s heritage museums. Though truthfully, Cambridge is better experienced in three dimensions. Take the town by storm and see it through one of the many river cruises and district tours available. The town has a burgeoning night life beyond the shoreline, however. Visit High Street, called one of the most beautiful in the nation by author James Michener or the Blackwater National Wildlife Refuge. Lastly, be sure to taste the oysters, crabs and fish which were crucial to the town’s prosperity at its founding and are still an integral part of Cambridge’s lifeblood today.
Cape Charles, Virginia
This family-friendly beach town on Virginia’s cape has something for everyone, especially shutterbugs. For travelers in search of the perfect picture, Cape Charles is a photographer’s paradise. Swing by Peach Street Books to see possibly the most adorable bookstore in the Mid-Atlantic where baked goods and coffee are always in stock. Laze in the lapis lazuli waters of the bay and finish up the day with a new twist on an old classic at Buskey Cider. There, fresh Virginia apples are distilled into seasonal cider varieties like Habanero Mango and Watermelon Rosemary. For a meal, visit the Hook at Harvey. Pro tip: book a table outside for an unbeatable view of the sunset.
Chesapeake City, Maryland
Beautifully maintained Victorian and Colonial-era homes await down by the bay in Chesepeake City. Traipse through the Ben Cardin C&D Canal Trail to take it in at the water’s edge. The town has worked hard to preserve its 19th-century feel and it shows. Narrow streets and knick-knack shops give the town a distinct seaside atmosphere. The town’s historic district is full of brickwork, with many of the homes having been built in the 1800s. Chesapeake City is also built on one of the largest working commercial canals in the world. Visitors and residents alike are treated to a full view of outgoing ocean-bound ships. The town has a variety of companies which offer aquatic tours for those who wish to see the bay’s traffic up close.
Chestertown, Maryland
This historic college town sitting on the banks of the scenic Chester River is absolutely bursting with small-town charm. From the extensive red brickwork lining Chestertown’s streets to the natural beauty of the river, Chestertown is an underappreciated but overqualified entry on any list about the Chesepeake Bay. On the first Friday of each month, residents head downtown to shop, sip wine and mingle outdoors while perusing merchandise from the local shops. Or, rent a kayak and travel up the Chester for a change of pace. Nature lovers will fawn over the Patapsco-McKeldin Loop in Patapsco Valley State Park. Before leaving, try Evergrain Bread Company for some delectable, mouth-watering croissants.
Irvington, Virginia
It has been said that Virginia is for lovers, and the town of Irvington in particular has a lot to love. A quintessential piece of Americana, this town of roughly 400 was called one of the 20 best places to live on the coast by Coastal Living Magazine in 2020 and it is easy to see why. White picket fences and billowing sails in the Rappahannock river abound in Irvington. Enjoy prime bay-to-table dining and pedal about this quaint shoreline town in Virginia’s river realm. Watch sailboat racing at the annual Turkey Shoot Regatta from the shore for an exhilarating evening. Want to try sailing? Home of one the East Coast’s premier sailing schools, Irvington is the perfect place to learn the ropes.
Onancock, Virginia
Tucked between the Chesepeake Bay and the Atlantic Ocean, Onancock was called “the Gem of the Eastern Shore'' by Captain John Smith, the famous English explorer in the 1600s. Today, this vibrant town of 1,500 is chock-full of attractions and more than holds its own against the other entries on this list. Travel Onancock Creek by kayak up to a local winery before visiting the island of Tangier from the town’s port. Revel in a thriving art scene on the Chesepeake Bay at the town’s live theater which has been hosting performances for more than 35 years. See a performance put on by Main Stage Productions before stopping by one of the many artisan studios Onancock has. Apparently, something about the town and the bay nearby inspires artistic expression and it is easy to see why.
St. Michaels, Maryland
Maryland is known for its succulent seafood and the inviting town St. Micheals is an excellent place to try it. The Maryland blue crab is renowned for its delicious, fatty meat and one would be hard pressed to find a restaurant in town where this crustacean was not on the menu. If oysters are preferred, try an oyster harvesting tour and get elbow-deep in a centuries-old tradition on the Eastern Shore. Sail Selina II comes highly recommended while in St. Micheals and is a wonderful way to spend an evening. The company offers cruises out into the bay on a gorgeous mahogany Roaring 20s era boat. Only a short drive away from St. Michaels, Tilghman Island is a small island which beckons visitors for a day in the natural beauty Maryland has to offer. Enjoy birdwatching, fishing and kayaking on an island with a reputation for top-notch hospitality.
Urbanna, Virginia
For seafood aficionados traveling to the Chesepeake Bay, a visit to Urbanna should be on the docket. This town of pretty, manicured streets along the Rappahannock River is home to the state’s largest oyster festival every November. The Urbanna Seafood & Raw Bar does offer half shell oysters year-round, however, but this town has so much more in store than shellfish. Walk the docks and listen to the sound of lapping waves, wander the quiet streets until sunset when the water comes alight in orange glow. This town boasts “more boats than folks,” and is an exemplary way to destress and decompress into the island groove (at least when the oyster festival is not on).
Rock Hall, Maryland
What began as another sleepy town on the shores of the Chesapeake at its founding has become a boaters paradise. Located at the mouth of the Chester River, this town of under 1,500 boasts over 10 marinas, a yacht club and world-class sailing. Head to Ferry Park to find Rock Hall’s small but pretty beach for an amazing view of the bay at sunset. Try the innovative cuisine like fruit pizza at the famed Dockside Cafe or pick up a pair of root-beer floats at Durding’s Store. Rockhall has an unmistakeable fishing town feel. To explore, start on Main Street and work towards the Waterman’s Museum for a dive into Rock Hall history.
There is no wrong way to explore the Chesepeake Bay. Truly, when it comes to seeing the charm and inviting hospitality of these towns along the estuary, the only question should be: where to start? Dining on the waterfront has never seemed so good. Delicious Maryland Blue Crab, endless oysters are the least of what Maryland and Virginia have to offer to their visitors. From birdwatching to sailing to doing nothing at all on quiet, tucked away beaches, it is safe to say the Chesepeake Bay has something for everyone.
