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

8 Delightful Towns To Visit In Chesapeake Bay

Separated from the expansive Atlantic Ocean by the huge Delmarva Peninsula, Chesapeake Bay, occupying the Mid-Atlantic region, is the world’s third-largest and the United States’ biggest estuary. With about 3,600 floral and faunal species and over 18 million people inhabiting the region, the Chesapeake Bay watershed stands out for its incredible history, crucial socio-economic significance, and amazing beauty. Furthermore, this 30-mile-wide and 200-mile-long bay, whose northern part is bounded by Maryland and the southern part by Virginia, is the principal attraction of umpteen vacationers who annually visit populous metropolises such as Annapolis, Baltimore, and Virginia Beach. Nevertheless, the countless delightful towns peppering the shores of the bay captivate tourists with their inviting ambiance and are, therefore, worth exploring on your next holiday to this portion of the country.

Cambridge, Maryland

Aerial view of a resort in Cambridge, Maryland
Aerial view of a resort in Cambridge, Maryland. Editorial credit: EQRoy /

Dorchester County’s seat of government, Cambridge, is one of the oldest colonial towns of the ‘Free State’ situated on the Choptank River’s southern shores, near the Chesapeake Bay’s eastern banks and to the north of the Blackwater National Wildlife Refuge. Founded as a nautical town in the beginning, Cambridge’s strong heritage is accurately reflected by the scores of vintage properties on the High Street as well as the distinct museums like the Neild Museum & Herb Garden, Harriet Tubman Museum & Educational Center, and Richardson Maritime Museum & Boatworks. When in town, browse the one-of-a-kind shops, clothing stores, art galleries, and comfy eateries such as Snapper’s Waterfront Café, Portside Seafood Restaurant, Cindy’s Kitchen, etc., that fill the carefully restored downtown.

Urbanna, Virginia

Urbanna Virginia historical district, seen from Cross Street
The historical district in Urbanna, Virginia. Image credit: Mojo Hand via Wikimedia Commons.

This tranquil colonial port town in Middlesex County, christened after Queen Anne of England, is located on the namesake Urbanna Creek directly off the Rappahannock River of Chesapeake Bay. Multiple buildings in Urbanna have been in use uninterruptedly since colonial times, with the 72-acre Urbanna Historic District comprising 65 such contributing properties, including the James Mills Storehouse, Old Middlesex County Courthouse, Wormeley Cottage, Gressitt House, Sandwich (Old Customs House), Landsdowne, and many more. The two public parks, Waterman’s Park on Kent Street and Taber Park at the corner of Rappahannock Avenue and Bonner Street, offer a range of recreational activities. Moreover, a temporary marina is managed by the town at Urbanna Creek’s Upton’s Point, while world-famous camping facilities are provided for the adrenaline junkies at the Bethpage Camp Resort. Sample fresh, locally sourced oysters at the Urbanna Seafood Restaurant & Bar apart from partaking in the Urbanna Oyster Festival, “Art on the Half Shell,” and Founder’s Day event every year.

Rock Hall, Maryland

Main Street in Rock Hall, Maryland.
Main Street in Rock Hall, Maryland. Image credit: Captain Bluecrab via Wikimedia Commons.

Called ‘Rock Hall Crossroads’ at the outset, this cozy waterfront settlement in Kent County, placed precisely at the edge of Maryland Route 20 on the National Chesapeake Scenic Byway, is around 13 miles southeast of Chestertown. Being the kernel of the maritime industries of the county, Rock Hall is a mind-blowing recreational boating destination providing travelers with excellent sailing, cruising, and paddling opportunities. Miscellaneous shops like the Hickory Stick Boutique and Sweet Cheeks Delightful Treats fill the town’s Main Street. Tourists visiting Rock Hall should enjoy a sunset cruise down the Chesapeake Bay aboard the 43’ “Island Girl” vessel, survey the infinite highly developed marinas and the Waterman’s Museum, take a quick bite at any of Rock Hall’s seafood restaurants like Harbor Shack and Waterman’s Crab House; and try to be present at the various yearly events like Witches of Rock Hall Weekend, Pirate & Wenches Weekend, and FallFest.

Cape Charles, Virginia

Aerial view of beach homes in Cape Charles, Virginia
Aerial view of beach homes in Cape Charles, Virginia.

A quaint seaside town, Cape Charles sits right on the Chesapeake Bay at the Delmarva Peninsula’s southern extremity in Northampton County. Abutted by King’s Creek to the north and Old Plantation Creek to the south, this town, initially established in 1884 as a planned railroad community, presently draws sightseers to have a look at its elegant Victorian-era structures in the Cape Charles Historic District and the ultra-clean Cape Charles Town Beach - the lone public beach on Virginia’s Eastern Shore. Multiple specialty shops, trendy boutiques, museums, bookstores, art galleries, bed & breakfasts like the Bay Haven Inn of Cape Charles, and eateries like Hook @ Harvey - a Cape Charles Bistro specializing in locally sourced seafood, line the town’s walkable commercial district. The Chesapeake Bay Bridge Tunnel, Cape Charles Harbor & Marina, Kiptopeke State Park, Fun Pier (adjacent to Cape Charles Town Beach), Eastern Shore of Virginia National Refuge, and the neighboring Cape Charles Natural Area Preserve are some noteworthy attractions. As an acclaimed arts & cultural mecca, Cape Charles hosts the yearly ‘Harbor for the Arts Summer Festival’ - considered the Virginia Eastern Shore’s biggest summer outdoor concert program.

Chesapeake City, Maryland

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

Initially referred to by Augustine Herman - a Bohemian explorer, as “Bohemia Manor,” this adorable Cecil County community was rechristened in 1839 after the Chesapeake & Delaware Canal. Divided into northern and southern segments as a result of the canal’s construction, Chesapeake City is the sole town of the Old Line State to be placed along an operational commercial canal. Visitors must take note of the town’s countless 19th-century structures located on the southern banks of the canal that currently house boutiques, retail shops, entertainment spaces, antique stores, art galleries, museums like the C&D Canal Museum, finest bed & breakfasts like The Blue Max Inn, and restaurants such as Bayard House Restaurant and the Chesapeake Inn Restaurant & Marina. The largely residential northern segment is widely known for the Schaefer’s Restaurant & Canal Bar and the Ben Cardin Recreational Trail, which links the town with Delaware City.

Onancock, Virginia

Onancock, Virginia
Market Street in Onancock, Virginia. Editorial credit: John Blottman /

Labeled “the Gem of the Eastern Shore,” Onancock is a pleasant Accomack County town that serves as an indisputable stopover point for exploring the remaining part of Virginia’s Eastern Shore. Having just 1,263 residents, the tight-knit community has superbly maintained its residential character and boasts a downtown district having an exceptional cultural milieu, top-notch eateries like Mallards at the Wharf, boutique hotels like The Charlotte Hotel & Restaurant, museums, and a live theater. The 225-acre Onancock Historic District includes significant residential and commercial properties of the town such as Scott Hall, Onancock Town Hall, Cokesbury United Methodist Church, Ker Place, Hopkins & Brother Store, etc. The town’s old-time Roseland Theater hosts an international film festival where a popular international film is shown to the public every month. Hop aboard the Tangier Onancock Ferry from May to October and get easy access to some of the highly valued assets of the Chesapeake Bay.

Easton, Maryland

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

The administrative center of eastern Maryland’s Talbot County, Easton occupies the tidewater region by the eastern banks of the Chesapeake Bay, not far from the head of Tred Avon River, approx. 70 miles east of Washington D.C. This tiny waterfront community welcomes holidaymakers to check out historical properties, booming arts scene, modern cafes, myriad locally-owned shops in the Tred Avon Square Shopping Center, and first-class restaurants like Hunter’s Tavern Restaurant & Bar serving authentic Eastern Shore cuisines. The Third Haven Friends Meeting House, Pickering Creek Audubon Center, the 19th century Trinity Cathedral, Adkins Arboretum, Avalon Theatre, Academy Art Museum, and Talbot County Historical Society Auditorium are must-visits. Every year, thousands of merrymakers flock here to attend the famed Waterfowl Festival and witness a carnival and fireworks show at the Fourth of July festivities.

Irvington, Virginia

Rappahannock River, Irvington, Virginia
The Rappahannock River in Irvington, Virginia.

Irvington, formally named in honor of Captain Levin Irvington - a Baltimore native, is a picturesque coastal village alongside the Rappahannock River and Carter’s Creek banks on the Northern Neck Peninsula in Lancaster County. The National Register-listed Irvington Historic District spread over 1,107.2 acres, comprises more than 149 contributing properties having different architectural styles. Irvington entices vacationers to spend a nice afternoon viewing ospreys by the side of Carter’s Creek; tour the Historic Christ Church & Museum and Steamboat Era Museum, go golfing at the Golden Eagle Golf Club; peruse the prize-winning Irvington Farmers Market aside from the various boutiques and souvenir shops; gorge on Rappahannock River oysters and fresh coastal cuisines at Fish Hawk Oyster Bar in Tides Inn; gaze in wonder at the pretty Creekside houses while cruising; and sample wines at the Dog & Oyster Vineyard.

From Onancock, Virginia - ‘the Gem of the Eastern Shore’ to the teeny community of Easton in eastern Maryland, the innumerable enchanting towns in the Chesapeake Bay region fascinate vacationers with their exclusive charisma. Set off on a tour of these gorgeous locales and cherish their diverse natural settings, unbelievable maritime heritage, finger-licking seafood meals, abundant recreational activities, and vibrant celebrations throughout the year. So, whenever you are on the lookout for beautiful places to spend some memorable moments with loved ones, look no further than these bewitching Chesapeake Bay communities.

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