12 Most Scenic Towns on the Chesapeake Bay
Situated in the Mid-Atlantic region and separated by the Delmarva Peninsula from the vast Atlantic Ocean, the Chesapeake Bay, covering a surface area of 4,479 sq. mi, is the United States’ most expansive estuary. This 200-mile long and 30-mile-wide bay, whose northern part is bordered by Maryland and the southern part by Virginia, is famed for its beauty and abundant marine life. Although uncountable vacationers flock to prominent locations like Annapolis, Baltimore, and Virginia Beach every year, there are many postcard-pretty towns dotting the shores of the bay that provide a welcoming ambiance and a chance for merrymakers to partake in various recreational activities on the waters of the Chesapeake Bay.
Chesapeake City, Maryland
Initially referred to as “the Village of Bohemia” by the Bohemian explorer Augustine Herman, this Cecil County town was renamed after the Chesapeake & Delaware Canal (C&D Canal) in 1839. Split into northern and southern sides following the construction of the Chesapeake & Delaware Canal, Chesapeake City is Maryland’s only town located on a working commercial canal. A significant portion of the town’s National Register-listed, painstakingly maintained 19th-century architecture is found on the southern banks of the C&D Canal. Many of these restored structures house artist galleries, antique stores, retail shops, boutiques, entertainment venues, fine diners like the Bayard House Restaurant, and excellent bed & breakfasts. Some other attractions include the Chesapeake Inn - which serves fresh seafood and features an expansive outdoor seating area; the C&D Canal Museum – which tells stories of the canal’s creation; and a replica of lighthouses lining the canal. The mainly residential northern side is best known for the Schaefer’s Restaurant & Canal Bar and the 17-mile-long Ben Cardin Recreational Trail that connects Chesapeake City to Delaware City.
Onancock, Virginia
Called by Captain John Smith “the Gem of the Eastern Shore” in the 1600s, this delightful town in Virginia’s Accomack County serves as the perfect base for exploring the remaining portion of the state’s Eastern Shore. Beautifully preserving its residential character and home to just 1,263 inhabitants, Onancock boasts a downtown district with a live theater, museums, award-winning eateries, an unparalleled art scene, and varied accommodation options ranging from boutique hotels to premium bed & breakfasts. The Onancock Historic District encompasses 267 contributing properties, such as Scott Hall, Ker Place, Cokesbury United Methodist Church, Hopkins & Brother Store, etc. The 1950-era Roseland Theater still possesses the old-time charm and hosts an International Film Festival, where every month, a popular international film is made available for public viewing. From May to October, board the Tangier Onancock Ferry, which provides easy access to some of the most hallowed assets of the Chesapeake Bay.
Havre De Grace, Maryland
Havre de Grace, a small hamlet in Maryland’s Harford County, is located at the head of the Chesapeake Bay and the mouth of the Susquehanna River, about 40 miles northeast of Baltimore. Named by General Marquis de Lafayette after the French seaport of Le Havre, Havre de Grace is renowned for its waterfront views, marinas, elegant Victorian homes, beautiful parks, and exceptional museums. The Havre de Grace Promenade, Havre de Grace Yacht Basin, Concord Point Lighthouse, Decoy Museum, Lock House Museum, Havre de Grace Maritime Museum, and Steppingstone Museum are some of the town's remarkable attractions. The Susquehanna State Park and Millard Tydings Memorial Park offer plenty of opportunities for nature lovers to spend time amidst the natural surroundings.
St. Michaels, Maryland
Hailing itself as “The Heart & Soul of the Chesapeake Bay,” this Talbot County town, named after a 1672 Episcopal Parish on the banks of the Miles River, is one of the crowned jewels of the Eastern Shore of Maryland. Rich in history and proudly upholding its nickname, “the town that fooled the British,” the walkable downtown of St. Michaels is a treasure trove of early American architecture. Many of these stately mansions in and around the town currently function as bed & breakfasts, besides housing local stores and clothing boutiques. Some of the town’s exciting attractions include the St. Michael’s Museum, Chesapeake Bay Maritime Museum, Saint Michaels Mill, several historic bay vessels and skipjacks, and different art galleries like Gregorio Gallery, Hopkins Original Art, and The Clark Gallery of Fine Art. For the quintessential Maryland gourmet experience, head to the town’s enticing restaurants, such as The Crab Claw, Foxy’s Harbor Grille, Ava’s Pizzeria & Wine Bar, Bistro St. Michaels, and Justine’s Ice Cream Parlor.
Cambridge, Maryland
One of Maryland’s oldest colonial towns, Cambridge, the administrative center of Dorchester County, is located on the southern banks of the Choptank River, close to the eastern shores of the Chesapeake Bay and the north of the Blackwater National Wildlife Refuge. Initially established as a seaport community, the town’s rich heritage is well reflected in the multiple museums like the Harriet Tubman Museum & Educational Center, Richardson Maritime Museum & Boatworks, and Neild Museum & Herb Garden, as well as its innumerable historic properties on High Street. Cambridge’s revitalized downtown is filled with one-of-a-kind shops, art galleries, fashion boutiques, and various cozy restaurants like Portside Seafood Restaurant, Snapper’s Waterfront Café, and Black Water Bakery.
Urbanna, Virginia
Urbanna is an attractive colonial port town in Virginia’s Middlesex County located on Urbanna Creek, immediately off Chesapeake Bay’s Rappahannock River. Since the colonial period, several buildings in the town have remained in continuous use, with the Urbanna historic district encompassing 65 such landmark structures, including the James Mills Storehouse (currently housing the Urbanna Museum & Visitor Center), Gressitt House, Old Middlesex County Courthouse, Sandwich (Old Customs House), Wormeley Cottage, Landsdowne, etc. Urbanna has two public parks: Taber Park at the corner of Bonner Street and Rappahannock Avenue and Waterman’s Park on Kent Street, both of which offer a range of recreational activities. The town also manages a transient marina at Urbanna Creek’s Upton’s Point, and the Bethpage Camp Resort provides world-class camping facilities. Throughout the year, the Urbanna Seafood Restaurant & Bar is the best place to sample fresh local oysters with breathtaking sunset views. Annually, during the first weekend of November, about 50,000 to 75,000 visitors are drawn to the Urbanna Oyster Festival, where live music, parades, arts & crafts, oyster-shucking contests, various foods, and other children’s activities are major attractions. In addition, Urbanna also hosts “Art on the Half Shell” and Founder’s Day events.
Cape Charles, Virginia
Placed on the southern end of the Delmarva Peninsula, this picturesque beach town in Virginia’s Northampton County sits directly on the Chesapeake Bay and is bounded by King’s Creek in the north and Old Plantation Creek in the south. Initially a 19th-century railroading hub, Cape Charles currently capitalizes on its stately Victorian-era waterfront properties and the pristine Cape Charles Town Beach – the sole public beach on Virginia’s Eastern Shore. The town’s commercial center is packed with several specialty shops, antique stores, museums, summer rentals, bed & breakfasts, bakeries, and eclectic eateries. Some of the town’s other points of interest include the Chesapeake Bay Bridge-Tunnel, Fun Pier (adjacent to the Cape Charles Town Beach), Cape Charles Harbor & Marina, Kiptopeke State Park, Central Park, the 29-acre Cape Charles Natural Area Preserve and the Eastern Shore National Wildlife Refuge. Being a significant arts and cultural center, the town hosts an annual Harbor for the Arts Summer Festival, the biggest summer outdoor concert program on the Eastern Shore of Virginia.
Rock Hall, Maryland
Originally known as “Rock Hall Cross Roads,” this waterfront town in Maryland’s Kent County is placed right on the National Chesapeake Scenic Byway at the end of Route 20, about 13 miles southeast of Chestertown. As the heart of Kent County’s maritime industries, Rock Hall is a top-class recreational boating destination offering vacationers some of the finest sailing, paddling, and cruising waters. The town’s Main Street features a variety of shops like the Hickory Stick Boutique, Sweet Cheeks Delightful Treats, and Hook Line-N-Tackle Shop. Aboard the 43’ “Island Girl” vessel to enjoy a sunset cruise along the Chesapeake Bay, explore the Waterman’s Museum and the innumerable sophisticated marinas, grab a bite at one of the town’s seafood restaurants, and take part in the various annual events like the Pirate & Wenches Weekend, Fallfest, and Witches of Rock Hall Weekend.
Easton, Maryland
Talbot County’s seat, Easton, is in the tidewater region along the Chesapeake Bay’s eastern shore, close to the head of Tred Avon River, about 70 miles east of Washington D.C. This small seaside town on Maryland’s Eastern Shore welcomes tourists to discover its landmark properties, vibrant arts scene, a variety of independent stores in an around the Tred Avon Square Shopping Center, trendy cafes, and excellent restaurants serving delicious American cuisines. The Third Haven Friends Meeting House, the 19th-century Trinity Cathedral, Avalon Theatre, the Talbot County Historical Society Auditorium, Academy Art Museum, Adkins Arboretum, and Pickering Creek Audubon Center are some of Easton’s must-visit attractions. Every year, this tight-knit community attracts thousands to a carnival and display of fireworks at the Fourth of July celebrations and the world-famous Waterfowl Festival each November.
Irvington, Virginia
Irvington is a quaint coastal village on the Northern Neck peninsula along the shores of Carter’s Creek and the Rappahannock River in Virginia’s Lancaster County. Named in honor of Captain Levin Irvington, a Baltimore native, the town’s Irvington Historic District, covering an area of 1,107.2-acre includes more than 149 contributing structures. The town attracts visitors of all ages to spend an afternoon watching ospreys along Carter’s Creek; explore the various museums like the Steamboat Era Museum and Historic Christ Church & Museum; check out the Irvington Farmers Market and other souvenir shops and boutiques; stay at the iconic Tides Inn or Hope & Glory Inn; dine on fresh fish and Rappahannock River oysters at the town’s fantastic eateries; play golf at the Golden Eagle Golf Club; enjoy Carter’s Creek & Rappahannock cruises; or bike to the dog-friendly Dog & Oyster vineyard.
Oxford, Maryland
A pleasant town and erstwhile colonial port in Maryland’s Talbot County, Oxford is one of the state’s oldest settlements, surrounded by the Tred Avon River to the north and west and the Town Creek to the east. Travel back in the past as you stroll through the picket fence-lined streets interspersed with restored colonial architecture in the Nationally-Registered Oxford Historic District. The town’s history continues through the Oxford-Bellevue Ferry, the country’s oldest privately owned ferry service that links Oxford with Bellevue and offers stunning views of the Chesapeake Bay. Tourists can spend some time biking around the town; attending a theater performance at the Oxford Community Center; browsing the numerous stores and museums like the Oxford Museum; enjoying a scoop of homemade ice cream at a local ice cream creamery; and savoring delicious seafood at one of the town’s fine-dining establishments. As a yachting paradise, Oxford hosts at least three sailing regattas during the warmer months, and with several marinas, it is an apt location for cruising boaters to dock after a weeklong cruise.
Deltaville, Virginia
Deltaville, often referred to as the “Boat Building Capital of the Chesapeake Bay,” is a census-designated place situated on Middlesex County’s eastern edge, bounded by the Piankatank River in the south, the Chesapeake Bay in the east and the Rappahannock River in the north. Dotted with countless boatyards, marinas, and marine-related businesses, Deltaville is an ideal vacation destination for those who want to enjoy water-based recreational activities. Travelers must tour the 36-acre Holly Point Nature Park, which acts as a setting for the Deltaville Maritime Museum, the historic F.D. Crockett buyboat, a waterfront performance area, outside exhibits, and a multi-purpose events pavilion. Throughout the year, the Museum & Park also hosts farmer’s markets, outdoor concerts, plays, and other Holiday events like Family Boatbuilding Week. On a Saturday night, athletic lovers can enjoy a “Deltaville Deltas” game and pride for this half-century-old semi-pro baseball team at the vintage Deltaville Ballpark – the state’s last remaining all-wooden baseball stadium along the banks of Sturgeon Creek. After a hectic day of exploration, taste the lip-smacking soft-shell crab sandwiches at The Table.
From the gorgeous Chesapeake City in Maryland to the tranquil Deltaville in Virginia, the umpteen scenic towns in the Chesapeake Bay region are waiting to be discovered. Embark on a tour of these enchanting locales and appreciate their varied natural sceneries, incredible maritime heritage, colorful annual celebrations, and mouthwatering cuisines. Whether you are planning a quick weekend trip or an extended vacation, these alluring Chesapeake Bay towns are worthy places to escape the stress of everyday life.
