The 10 Best Towns On The Chesapeake Bay For A Two-Day Recharge
Parted by the Delmarva Peninsula from the mighty Atlantic, the Chesapeake Bay is the United States’ largest estuary, with its 64,299 sq mi catchment area encompassing one of the nation’s most economically significant regions. Scattered along the bay in the states of Maryland and Virginia are innumerable soulful towns that deliver maximum tranquility in a minimal span of time. These close-knit shoreline communities, with their eye-catching surroundings, walkable main streets, pristinely preserved architectural treasures, fresh seafood joints, excellent recreation areas, and comfortable lodgings, are ideal for all those looking for a rejuvenating two-day escape.
Saint Michaels, Maryland
Saint Michaels is a pretty Talbot County town located on Maryland's Eastern Bay by the banks of the Miles River. Firmly endorsing the moniker, “the town that fooled the British during the War of 1812,” and upholding its seafaring heritage, Downtown Saint Michaels is apt for gentle walks among baronial Victorian properties, antique outlets such as Antiques on Talbot LLC, and unique boutiques like The Preppy Redneck. Stop by Chesapeake Bay Maritime Museum, noting its extensive collection of Chesapeake Bay boats and interactive exhibits on local maritime history. To appreciate the town’s culinary specialities, drop in at Foxy’s Harbor Grille, and get some sleep at St. Michaels Harbour Inn, Marina & Spa.
Urbanna, Virginia
Named in tribute to Queen Anne of England, Urbanna is a quaint Middlesex County town set along the Urbanna Creek right off the Rappahannock River, close to the Chesapeake Bay. Rich in nautical heritage and small-town enchantments, this colonial port town combines riverscapes with a walkable historic district crammed full of colonial-era buildings, such as the 1758-built Sandwich/Old Customs House, and the 1750-built Wormeley Cottage/Wormeley-Montague House. Visit Waterman’s Park in a residential area on Kent Street for picnicking and unimpeded views of the Rappahannock River. If you prefer a nature-oriented stay plus family-friendly amenities, look no further than the Bethpage Camp-Resort, and set aside some time from your busy schedules for a taste of local oysters, live music, parades, etc., at the yearly Urbanna Oyster Festival.
Rock Hall, Maryland
Formerly labeled ‘Rock Hall Crossroads,’ this homey waterside community in Kent County is situated at the terminus Maryland Route 20, just 13 miles southeast of Chestertown. Currently a sailing, fishing, and recreational boating destination on the Chesapeake Bay’s upper Eastern Shore, Rock Hall offers superb water sports activities for every vacationer. Have fun while on a sunset cruise down the bay aboard the ‘Island Girl’ sailing vessel of the Blue Crab Chesapeake Charters. Embark on a self-guided tour browsing one-of-a-kind exhibits on fishing, oystering, and crabbing at the Waterman’s Museum in Haven Harbour Marina. Savor seafood and classic American fare at the upbeat Harbor Shack, and rest for the night at the highly-rated Inn at Haven Harbour.
Irvington, Virginia
Home to just 474 residents as per the 2020 US Census, Irvington, an arresting town in Lancaster County, occupies the Northern Neck Peninsula, by the banks of the Carter’s Creek and Rappahannock River. Wander the streets of the National Register-listed Irvington Historic District, inspecting the many architecturally diverse contributing buildings. Spend a nice noontime onboard a bird-watching cruise observing ospreys, eagles, and nesting herons at Carter’s Creek. Feast on fresh seafood and oysters coupled with craft beers, bright cocktails, and special wines at The Dredge. Procure premium-quality products from the prize-winning Irvington Farmers Market, and slack off at the chic Hope & Glory Inn.
Havre de Grace, Maryland
Christened after Le Havre, a principal port city in northern France, Havre de Grace sits at the meeting of the Susquehanna River and Chesapeake Bay, roughly 40 miles northeast of Baltimore. Flaunting oceanfront vistas, stately Victorian residences, outstanding museums, scenic parks, and gourmet hideaways, Havre de Grace is indeed a refreshing getaway. Walk slowly along the Havre de Grace Promenade, easily reaching the 36-foot-tall Concord Point Light, the second-oldest publicly accessible lighthouse in the state. Find out about the Bay’s decoy-making and waterfowling traditions at the Havre de Grace Decoy Museum and step into the artifact and period-furnished rooms of the Lock House Museum that preserve the storied past of the Susquehanna and Tidewater Canal. Thoroughly enjoy picnics and outdoor activities in the Millard Tydings Memorial Park, and select The White House of Havre de Grace for a restful stay.
Onancock, Virginia
Called the ‘Gem of the Eastern Shore’ by the English explorer John Smith, Onancock is a teeny harbor town in Accomack County, acclaimed for its creative atmosphere and peaceful coastal settings. At the time of your visit to Onancock, be sure to check out the Federal-style Ker Place, an early 1800s historic house museum, and the multitudinous historical exhibits in the Waterman’s Museum & Research Center that tell tales of the Eastern Shore’s glorious maritime past. Furthermore, watch live theatrical performances at the North Street Playhouse, catch many national and international films at the Roseland Theatre, and sample luscious Eastern Shore fare at Mallards at the Wharf. For a stress-free stay, the refined Inn at Onancock is a prime choice.
Chesapeake City, Maryland
This only 736-resident town in northeastern Maryland’s Cecil County, titled after the Chesapeake & Delaware Canal, draws tourists with its spectacular canal views, historic allure, outdoor trails, and waterside peacefulness. Bisected into northern and southern sections thanks to the C&D Canal’s construction right through the town’s heart, Chesapeake City is at present Maryland’s lone settlement situated parallel to an operating commercial canal. A majority of the town’s intact 19th-century buildings, built on the southern banks of the C&D Canal, house museums like the C&D Canal Museum, gift shops like The Mercantile at Back Creek, and accommodations such as the Inn at the Canal Bed & Breakfast. The town’s largely residential northern section features maritime-themed seafood dining establishments like Schaefer's Canal House, as well as the Ben Cardin C & D Canal Recreational Trail, which travels along the canal offering close-up views of working commercial vessels.
Cape Charles, Virginia
Located on Virginia’s Eastern Shore near the mouth of the Chesapeake Bay, Cape Charles is a seashore community with industrial roots. Initially established as a planned railroad town bordered by the King’s Creek in the north and Old Plantation Creek in the south, Cape Charles invites sightseers to observe the exquisitely maintained late-19th and early 20th-century properties in the Cape Charles Historic District. The town’s business district is perfect for casual strolls, in addition to checking out the numerous seafood eateries, such as The Shanty, art galleries like Lemon Tree Gallery & Studio, and plush bed & breakfasts like the Bay Haven Inn of Cape Charles. Beach lovers at the Cape Charles Town Beach should not miss their morning ambling, swimming, sunbathing, and other coastal recreations, while more hikerly types must survey the maritime forest habitats, coastal beach, and dunes at the nearby Cape Charles Natural Area Preserve.
Oxford, Maryland
A former colonial port town in Talbot County, Oxford is one of Maryland's oldest communities, set on a narrow peninsula bordered to the east by the Town Creek, and to the north and west by the Tred Avon River. Travel back in time while strolling the tree-lined streets of Oxford Historic District, overflowing with beautifully preserved 18th and 19th-century homes. Hop aboard the Oxford-Bellevue Ferry, the country’s oldest privately operated ferry service, which links Oxford with Bellevue across the Tred Avon River, proffering sweeping panoramas of the Chesapeake Bay. Discover more about the town’s past through the assorted history exhibits displayed at Oxford Museum. Relish mouthwatering fresh Chesapeake seafood at Doc’s Sunset Grille, and do not miss a scoop of housemade ice cream at Scottish Highland Creamery. De-stress at the Sandaway Suites & Beach, a premier boutique hotel in the Eastern Shore for relaxation, romance, and seafaring atmosphere.
Deltaville, Virginia
Deltaville sits at the end of a peninsula facing the Chesapeake Bay, and is oftentimes referred to as the ‘Boat Building Capital of the Chesapeake Bay.’ With dozens of dockyards, marinas, and maritime businesses peppered throughout the town, Deltaville is a quintessential holiday haven for anybody seeking a serene escape by the water. Dive into Deltaville’s boat-building history at the Deltaville Maritime Museum, set in the 36-acre Holly Point Nature Park, where visitors get to explore the walking trails, recreational amenities, and open spaces for various community events, festivals, and farmers’ markets. Enjoy a baseball game with Deltaville Deltas at the Deltaville Ballpark, the oldest all-wooden baseball stadium in the state. Savor delectable soft-shell crab sandwiches served at The Table Market & Restaurant, and have a relaxing stay at the Deltaville Dockside Inn adjacent to Broad Creek.
Recharging In The Best Towns Along Chesapeake Bay
From the strong maritime & colonial heritage of Oxford, Maryland, to the Victorian charm & laid-back beaches of Cape Charles, Virginia, the unparalleled oceanfront settlements in the Chesapeake Bay region spellbind weekenders with their charismatic magnetism. Provided you want to be impressed by the copious maritime attractions, take calm promenades through the downtown area, partake in out-of-doors activities and seasonal gatherings at shoreline parks, and unwind in cozy stays, these Chesapeake Bay towns will make you accept that at the end of your short 48-hour sojourn here, you you've been completely refreshed.
