8 Most Hospitable Towns In Chesapeake Bay
Sandwiched between the North American mainland in the west and the Delmarva Peninsula in the east, the 200-mile-long and 30-mile-wide Chesapeake Bay is the largest and at one time the most productive estuary of the North Atlantic in the continental United States. With the bay’s northern portion being bounded by Maryland and its southern portion by Virginia, the Chesapeake Bay holds great socio-economic significance for the entire region. The Chesapeake Bay is the star attraction, and eight most hospitable towns in the region enrapture holidaymakers with their welcoming ambiance and culture of togetherness.
Easton, Maryland
Talbot County’s administrative capital, Easton, is set on the eastern shores of the Chesapeake Bay in the tidewater region, in the vicinity of the head of Tred Avon River, around 70 miles east of Washington, D.C. Encompassing a substantial portion of the heart of this pretty coastal town in eastern Maryland is the National Register-listed Easton Historic District which comprises a large number of contributing structures such as Avalon Theatre, Talbot County Courthouse, Third Haven Friends Meeting House, etc. Side by side, inspect the numerous domestically owned shops in Tred Avon Square Shopping Center, the art exhibitions held at the Academy Art Museum, the bona fide Eastern Shore fares served by the Hunter’s Tavern Restaurant & Bar, and attend the annual Waterfowl Festival in November.
Urbanna, Virginia
Urbanna, named for Queen Anne of England, is a serene colonial port town situated on the homonymous Urbanna Creek right off the Rappahannock River of Chesapeake Bay. Several buildings in this Middlesex County town have been in use persistently since the colonial period, and 65 such contributing buildings, like the Old Middlesex County Courthouse, Wormeley-Montague House, and Sandwich (Old Customs House), are included within the 72-acre Urbanna Historic District. Vacationers can partake in an array of recreational activities at the town’s two public parks: Taber Park and Waterman’s Park; undertake camping activities at the Bethpage Camp Resort; taste recently harvested oysters at Urbanna Seafood Restaurant & Bar; and take part in the Urbanna Oyster Festival held yearly on the first sequent Friday and Saturday of November.
Chesapeake City, Maryland
Initially termed "Bohemia Manor" by the Bohemian explorer Augustine Herman, and later renamed after the Chesapeake & Delaware Canal, this appealing Cecil County town is home to only 736 inhabitants as per the 2020 US Census. Halved into northern and southern divisions owing to the construction of the canal right through the core of the town, Chesapeake City is the solitary Free State settlement that is sited along a running commercial canal. Placed on the C&D Canal’s southern banks are numerous 19th-century edifices housing clothing accessory stores like Chick’s, gift shops like The Mercantile at Back Creek, museums like the C&D Canal Museum, and eateries like the Chesapeake Inn Restaurant & Marina. The chiefly residential northern division is well-known for the nautical-themed seafood restaurant Schaefer’s Canal House and the Ben Cardin C & D Canal Recreational Trail that links Chesapeake City’s Lock Street with the Michael Castle Trail at the Maryland-Delaware state line.
Irvington, Virginia
Christened in memory of Captain Levin Irvington, Irvington is a photographic waterside hamlet in Lancaster County, located by the shores of Carter’s Creek and the Rappahannock River on the Northern Neck Peninsula. Spanning 1,107 acres, the Irvington Historic District features more than 149 architecturally diverse time-honored buildings. Travelers must not miss a tour of the Steamboat Era Museum and Historic Christ Church & Museum; spend one afternoon observing ospreys along the side of Carter’s Creek; feast on seafaring delicacies and Rappahannock River oysters at the Tides Inn’s Fish Hawk Oyster Bar; and note the superior quality products, crafts, and food displayed at the award-winning Irvington Farmers Market — touted as "The Best Farmers Market in Eastern Virginia" — slated for the first Saturday of every month from May to November.
Cambridge, Maryland
One of Maryland’s oldest colonial towns, founded in 1684 by English colonists, Cambridge, the town of Dorchester County, is located north of the Blackwater National Wildlife Refuge, along the southern banks of the Choptank River and adjacent to the Chesapeake Bay’s eastern shores. Flawlessly fusing nautical heritage and Eastern Shore customs with all the comforts of an unparalleled hospitality destination, tourists in this friendly community need to explore the dozens of classic High Street properties, plus discreet museums like the Harriet Tubman Museum & Educational Center, and Neild Museum & Herb Garden. When in Cambridge for a visit, scan the unique boutique shops like Butterfly Boutique, antique stores like The Heart of Dorchester Antiques, art galleries like Main Street Gallery, and restaurants like Christopher’s Corner that cram the artfully rejuvenated downtown.
Onancock, Virginia
Established in 1680 and called by Captain John Smith as "the Gem of the Eastern Shore," this teeny Accomack County town is an indispensable layover point for all those who wish to scout the rest of Virginia’s Eastern Shore. Having exactly 1,167 inhabitants (as per the 2020 US Census), Onancock has exquisitely preserved its suburban atmosphere and vaunts a downtown district with a nonpareil creative scene, the prize-winning North Street Playhouse, the Georgian-style Ker Place mansion, and the Watermen’s Heritage Museum in the Historic Onancock School Community & Cultural Center. Furthermore, the Hopkins & Brother Store, Cokesbury United Methodist Church, Roseland Theatre, and Hopkins-Beechlawn House are some unmissable sites of interest, as is a delightful ride aboard the Tangier Onancock Ferry that takes one to the pristine Tangier Island daily between the first weekend of May and the first weekend of October.
Saint Michaels, Maryland
Fondly dubbed “The Heart & Soul of the Chesapeake Bay,” Saint Michaels (aka St. Michaels) is a panoramic Talbot County town by the Miles River banks at the nucleus of the Eastern Shore of Maryland. Unwaveringly promoting its historic maritime identity, and the sobriquet “the town that fooled the British” earned during the War of 1812, St. Michaels’ Downtown is a receptacle of imposing Victorian structures, apart from gift shops like The Shops at Sea Captain’s Cottage, antique stores like Antiques on Talbot LLC, clothing stores like Chesapeake Bay Outfitters, art galleries like Studio 2 Saint Michaels, and noteworthy museums like the Chesapeake Bay Maritime Museum. For a quintessential Maryland culinary indulgence, head to some of the town’s choicest restaurants like Bistro St. Michaels and Foxy’s Harbor Grille.
Cape Charles, Virginia
An attractive waterfront settlement, Cape Charles sits on the Eastern Shore of Virginia, not far from Chesapeake Bay’s mouth at the southern edge of the Delmarva Peninsula in Northampton County. Set up as a planned railroad town in 1884 and flanked by the Old Plantation Creek to the south and King’s Creek to the north, Cape Charles allures excursionists with the immaculate Cape Charles Town Beach and the Cape Charles Historic District’s exquisite 19th-century structures. The town’s strollable business district is chock-a-block with gift shops like The Boardwalk, art galleries like Lemon Tree Gallery & Studio, seafood restaurants like The Shanty, and upscale bed & breakfasts like Bay Haven Inn of Cape Charles. When in town, the Cape Charles Harbor & Marina, Chesapeake Bay Bridge Tunnel, and the adjacent Cape Charles Natural Area Preserve are must-visit, besides turning up at the annual ‘Harbor for the Arts Summer Festival’ — considered to be the greatest summer outdoor concert program along Virginia's Eastern Shore.
From finding pleasure in Onancock’s Annual Crab Crackin’ Festival and Saint Michaels’ Chesapeake Bay Maritime Museum Festivals, the neighborly shoreline communities in the Chesapeake Bay region possess everything that can please the out-of-towners. Pursue exciting escapades in these magnetic Chesapeake Bay towns and admire their eclectic surroundings, strong oceanic heritage, luscious seafood delicacies, sheer number of outdoor opportunities, jazzy community festivals in every season, and the collective spirit of the townspeople.
