10 Picture-Perfect Towns On The Chesapeake Bay
Covering a surface area of 4,479 sq. mi, the Chesapeake Bay is the continental United States’ largest and most productive estuary situated in the Mid-Atlantic region and separated from the mighty Atlantic by the Delmarva Peninsula. Holding more than 18 trillion gallons of water, this roughly 200-mile-long and 30-mile-wide bay’s northern portion is bordered by Maryland and the southern portion by Virginia. The Chesapeake Bay is the main attraction for uncountable tourists who annually visit Maryland and Virginia’s popular urban metropolises like Baltimore, Virginia Beach, and Annapolis. However, dotting the shores of this expansive bay are innumerable picture-perfect towns that are worth exploring on your next Chesapeake Bay vacation.
Oxford, Maryland
One of Maryland’s oldest settlements, Oxford is a charming waterfront town and erstwhile colonial port in Talbot County, bounded by the Town Creek to the east and the Tred Avon River to the north and west. Visitors to Oxford can get a glimpse of the town’s glorious bygone days by walking along the tree-lined streets of the Nationally-Registered Oxford Historic District packed with well-preserved historic homes. The town’s rich heritage is also well reflected in the nation’s oldest privately owned ferry service – the Oxford-Bellevue Ferry that connects Oxford with Bellevue and provides spectacular views of the Chesapeake Bay. Travelers can browse the unique shops and museums like the Oxford Museum; watch a theater performance at the Oxford Community Center; grab some mouthwatering seafood at one of the town’s finest restaurants like the Robert Morris Inn, Doc’s Sunset Grille, and Pope’s Tavern at the Oxford Inn; and enjoy a scoop of handcrafted ice cream at a local icecream creamery. Being a yachting mecca, Oxford hosts around three sailing regattas during summer, while the town’s several beautiful marinas make it an ideal place to dock for cruising boaters.
Cape Charles, Virginia
An attractive tiny beach town in Virginia’s Northampton County, Cape Charles sits on the southern end of Delmarva Peninsula, directly on the Chesapeake Bay, surrounded by the Old Plantation Creek to the south and King’s Creek to the north. Initially founded as a planned railroad community in 1884, the town, at present, allures visitors to witness its quaint Victorian architecture in the Cape Charles Historic District and the immaculate Cape Charles Town Beach – the only public beach located on the Eastern Shore of Virginia. The town’s walkable retail district is packed with a plethora of specialty shops, art galleries, beachy boutiques, bookstores, museums, bed & breakfasts, and cozy restaurants. Some of Cape Charles’s other sites of interest include the Chesapeake Bay Bridge-Tunnel, Kiptopeke State Park, Eastern Shore of Virginia National Wildlife Refuge, Fun Pier (next to the Cape Charles Town Beach), the Cape Charles Harbor & Marina, Central Park, and the nearby 29-acre Cape Charles Natural Area Preserve. As a noted arts and cultural center, Cape Charles hosts an annual ‘Harbor for the Arts Summer Festival,’ considered the biggest summer outdoor concert program on Virginia’s Eastern Shore.
Chesapeake City, Maryland
Originally called “Bohemia Manor” by Augustine Herman, the Bohemian explorer, this town in Maryland’s Cecil County was renamed in 1839 after the Chesapeake & Delaware Canal. Separated into the northern and southern sections due to the C&D Canal’s construction, Chesapeake City is the sole town in Maryland that is located on a 14-mile-long working commercial canal. A major part of the town’s National Register-listed impressive 19th-century architecture is located on the canal’s southern banks. Many of these restored old homes currently house antique stores, boutiques, art galleries, entertainment spaces, excellent bed & breakfasts, museums like the C&D Canal Museum, and eateries like the Bayard House Restaurant, and the Chesapeake Inn. The primarily residential northern section is well-known for the 17-mile-long Ben Cardin Recreational Trail and the Schaefer’s Restaurant & Canal Bar.
Urbanna, Virginia
Named in honor of Queen Anne of England, Urbanna is a serene colonial port town situated on Urbanna Creek in Virginia’s Middlesex County, just off Chesapeake Bay’s Rappahannock River. Since the colonial era, numerous buildings in the town have been in continuous use, with the Urbanna Historic District comprising many landmark properties including the Old Middlesex County Courthouse, Sandwich (Old Customs House), James Mills Storehouse (currently home to the Urbanna Museum & Visitor Center), etc. The town’s two public parks: Waterman’s Park and Taber Park offer adventurers an array of outdoor recreations. World-class camping facilities are provided by the Bethpage Camp Resort while the Urbanna Seafood Restaurant & Bar is an ideal place to taste local oysters. Every year during the first weekend of November, thousands of merrymakers flock to the Urbanna Oyster Festival to participate in its oyster-shucking contests, parades, art & craft fairs, food stalls, live musical performances, etc. Urbanna also hosts “Art on the Half Shell” – a one-day outdoor art and craft show, and a Founders’ Day event.
St. Michaels, Maryland
This Talbot County town, named after a 1677 Episcopal Parish and located along the shores of the Miles River at the center of Maryland’s Eastern Shore, hails itself as “The Heart & Soul of the Chesapeake Bay.” Steeped in maritime history and aptly upholding its nickname “The town that fooled the British,” St. Michaels’s walkable downtown is a repository of early American architecture. At present, many of these stately Victorian structures house retail stores and clothing boutiques, apart from functioning as prominent bed & breakfasts. Some of the town’s noteworthy points of interest include the Chesapeake Bay Maritime Museum, the 19th century Saint Michaels Mill, St. Michael’s Museum, countless historic bay vessels and skipjacks, and various art galleries such as the Clark Gallery of Fine Art, Gregorio Gallery, and Hopkins Original Art. Spend some time at the town’s high-quality restaurants like Ava’s Pizzeria & Wine Bar, Justine’s Ice Cream Parlor, the Crab Claw restaurant, Bistro St. Michaels, and Foxy’s Harbor Grille for a typical Maryland gourmet experience.
Onancock, Virginia
Dubbed “the Gem of the Eastern Shore” by Captain John Smith, this inviting Accomack County town serves as an ideal stopover point for surveying the rest of Virginia’s Eastern Shore. Home to only 1,263 residents as per the latest US Census, Onancock amazingly preserves its residential character, with its downtown district chock-full of museums, live theaters, boutique hotels, award-winning restaurants, luxurious bed & breakfasts, and an unrivaled art scene. A large number of Onancock’s residential and commercial buildings such as Scott Hall, Cokesbury United Methodist Church, Hopkins & Brother Store, Onancock Town Hall, Ker Place, etc., are included within the 225-acre Onancock Historic District. The vintage Roseland Theater hosts an International Film Festival, where every month, a famous international film is shown to the public. From May to October, one can board the Tangier Onancock Ferry and easily access some of the Chesapeake Bay’s most venerable assets.
Easton, Maryland
The administrative center of Talbot County, Easton is in the tidewater region along the eastern shore of Chesapeake Bay, near the head of Tred Avon River, approximately 70 miles east of Washington D.C. Throughout the year, this tiny seaside town enchants tourists with its thriving arts scene, landmark structures, trendy cafes, superb eateries, and an array of locally-owned stores in and around the Tred Avon Square Shopping Center. Easton’s must-visit sites include the 19th-century Trinity Cathedral, the Talbot County Historical Society Auditorium, Adkins Arboretum, Avalon Theatre, the Third Haven Friends Meeting House, and the Pickering Creek Audubon Center. Thousands of revelers come to Easton to partake in an annual carnival and display of fireworks at the Fourth of July celebrations, and the famed Waterfowl Festival for three days every November.
Deltaville, Virginia
Often referred to as the “Boat Building Capital of the Chesapeake Bay,” Deltaville is a census-designated place on the eastern extremity of Virginia’s Middlesex County, bounded by the Chesapeake Bay in the east, the Rappahannock River in the north, and Piankatank River in the south. Sprinkled with scores of boatyards, marinas, and marine-related businesses, Deltaville is a perfect vacation destination for those who wish to participate in water-based recreation. Vacationers touring Deltaville must explore the 36-acre Holly Point Nature Park, which is home to the Deltaville Maritime Museum, the F.D. Crockett buyboat, a variety of outdoor exhibits, a multi-purpose events pavilion, and a waterfront performance area. All through the year, the town’s Museum and Park hosts farmer’s markets, concerts, plays, and other holiday events. Sports lovers can enjoy a “Deltaville Deltas” game at the Deltaville Ballpark – Virginia’s last remaining all-wooden baseball stadium along the shores of Sturgeon Creek. After a hectic day of exploration, grab some delicious soft-shell crab sandwiches at The Table and rest for the night at the Deltaville Dockside Inn.
Cambridge, Maryland
Dorchester County’s seat, Cambridge is one of Maryland’s oldest colonial towns located along the Choptank River’s southern banks near the eastern shores of the Chesapeake Bay and to the north of the Blackwater National Wildlife Refuge. Originally established as a seaport community, Cambridge’s rich heritage is well reflected in its many landmark properties on High Street as well as ample museums like the Neild Museum & Herb Garden, Harriet Tubman Museum & Educational Center, and Richardson Maritime Museum & Boatworks. The town’s revitalized downtown is jam-packed with fashion boutiques, one-of-a-kind shops, art galleries, and diners like Snapper’s Waterfront Café, Cindy’s Kitchen, Black Water Bakery, and Portside Seafood Restaurant.
Irvington, Virginia
Christened in honor of the Baltimore native Captain Levin Irvington, this quintessential American village in Virginia’s Lancaster County is located along the banks of the Rappahannock River and Carter’s Creek on the Northern Neck Peninsula. Encompassing an area of 1,107.2 acres, the Irvington Historic District comprises over 149 contributing buildings in different architectural styles. Irvington has much to offer and welcomes vacationers to spend an afternoon observing ospreys, eagles, and herons along Carter’s Creek; tour the Steamboat Era Museum and Historic Christ Church & Museum; browse the award-winning Farmers Market and other boutique shops, antique stores, and art galleries; dine on fresh fish and Rappahannock River oysters at the town’s classic eateries; stay at any one of the two nationally recognized inns: Tides Inn or Hope & Glory Inn; check out the beautiful Creekside homes while cruising the Carter’s Creek & Rappahannock River; play a round of golf at the Golden Eagle Golf Club; and bike to the dog-friendly Dog & Oyster vineyard to sample medal-winning wines.
From Oxford, Maryland to Irvington, Virginia, the umpteen postcard-pretty towns in and around the Chesapeake Bay are waiting to welcome vacationers. Each of these locales with breathtaking natural sceneries, rich maritime histories, lip-smacking seafood cuisines, and lively annual celebrations, will surely provide unforgettable memories for every visitor. So, whether you are in search of scenic places to tour on your weekend escapades or long vacations, look no further than these Chesapeake Bay towns.
