9 Secluded Towns on the Chesapeake Bay
The famed Chesapeake Bay is the biggest estuary in the United States and the largest inlet in the Atlantic Coastal Plain. The expansive inlet stretches from Maryland to Virginia and has many quaint coastal towns along its banks. The small hamlets and towns offer historic sites, exquisite dining options, and unique architecture that attract visitors annually.
Though the bigger cities are excellent destinations, the smaller, secluded port towns have an irresistible character. The port towns embrace the spirit of the bay with walkable downtown areas just feet from the commercial fishing boats that are the lifeblood for many. Secluded towns offer fewer crowds but many local interests that would be missed in the hustle and bustle of busier cities.
Tappahannock, Virginia
Tappahannock, Virginia, is a small historical hamlet bordering the Chesapeake Bay and the Rappahannock River. The town offers nearly 400 years of history, a small-town atmosphere, and noteworthy seafood restaurants. Essex County Historical Museum is an excellent starting point for discovering the town or taking a guided tour through over a dozen monuments and historical sites.
Among the notable restaurants is 1710 Tavern. Built in 1710, the fine-dining restaurant seamlessly integrates history with an exquisite menu. The built-in fireplace and decor express the tavern's historical significance, and casual dining is available on the back patio. For a more modern experience, one can enjoy some sports at the NN Burger Sports Bar, known for its lively atmosphere and delicious drinks.
Cape Charles, Virginia
Cape Charles, Virginia, is notable for its natural beauty and rustic attractions, among other attractive sites. The peninsular town is bordered by King's Creek, Chesapeake Bay, and Old Plantation Creek, a beautiful aesthetic and small-town charm. The Chesapeake Bay Bridge-Tunnel is easily acceptable and a must-see for new visitors. It keeps Cape Charles secluded from the mainland while still connected with towns like Norfolk and Virginia Beach.
Natural points of interest include the Eastern Shore National Wildlife Refuge and Kiptopeke State Park. The refuge is a paradise for bird watchers, hikers, and nature lovers. The state park has five miles of trails to explore, five lodges, and RV and primitive camping sites. Back in town, the charming commercial district has local restaurants like The Oyster Farm Seafood Eatery, many boutiques, and quaint architectural styles.
Irvington, Virginia
Irvington is a quaint and charming coastal community in Virginia known for its relaxing atmosphere and fresh seafood. The inviting atmosphere and scenery are best seen at Carter's Creek, where sailboats cruise on the breezes and wildflowers, vegetables, and folk art are on display. Irvington is also filled with charming and historic bed and breakfast-inns. The classic Hope and Glory Inn, ca. 1889, is a landmark three-story inn with eclectic rooms and a cozy feel. The boutique inn is within walking distance of historic sites and includes an oyster bar, micro vineyard, and many more accommodations. The Tides Inn is another boutique inn that is a big draw for many. It has a restaurant, quaint accommodations, and scores high reviews.
Oxford, Maryland
Oxford is a cozy coastal community in Maryland with charming architecture. It is an ideal relaxing getaway. It is also a haven for historic bed and breakfasts, notably the Robert Morris Inn. The inn has been open since 1710, making it one of the longest-running inns in the U.S.. For more history, visitors will appreciate the Oxford Museum, which has over 300 years of local artifacts and exhibits.
Downtown has many noteworthy restaurants, including Anthony's, which is one of the premier reasons to visit. Furthermore, the fare ranges from casual to sophisticated at places like Pope's Tavern and Capsize OXMD. The community also hosts many annual events, and the town comes alive in April during the Oxford Days festival, an excellent time to get to know the area.
Chesapeake City, Maryland
Chesapeake City, Maryland, is a historic bohemian colony originally named Village of Bohemia. The name changed in the 19th century, but the small community atmosphere is still there today. The town is part of the National and Maryland Register of Historic Places, and the Historic District is one of its main attractions. A short stroll through this area is loaded with rustic buildings showcasing Greek Revival, Italianate, and Federal architecture styles.
The Historic District is the entertainment hub and home to notable delicacies like Chesapeake Candy Works and cultural attractions like Chesapeake City Museum. The museum has many fascinating exhibits highlighting the local culture, including a tribute to its Ukrainian roots. The best way to see the town is on foot; there are numerous sites to discover and explore. Afterward, visitors can enjoy an evening stroll along the Ben Cardin C&D Canal Trail, which follows along Back Creek with lovely views.
Havre de Grace, Maryland
Havre de Grace, Maryland, is a scenic and traditional port town at the mouth of the Susquehanna River. The secluded town is known for its panoramic views, quaint atmosphere, and cultural points of interest. One of the landmark historical attractions is the Concord Point Lighthouse and Lighthouse Keeper's Museum. The structure was built in 1827 and is the oldest publically accessed lighthouse in Maryland.
The Havre de Grace Maritime Museum provides another fascinating opportunity to discover regional history in this coastal town through exhibits and guided tours. The town also has a vibrant artistic culture that can be explored at galleries like Arts by the Bay and Gallery 220.
St. Michaels, Maryland
St. Michaels, Maryland, is a charming town with deep maritime roots in the Chesapeake Bay. A historic landmark is the Chesapeake Bay Maritime Museum, home to the largest collection of boats from the bay. On the other hand, cruise lines like Patriot Cruises combine scenic views and heritage with tours past 200-year-old mansions and commercial structures.
The artsy and sophisticated bay town is home to several wineries, including St. Michaels Winery. The waterfront winery has an extensive list and is one of the best in the area. If you want a casual dining experience, the Crab Claw is a decades-old main attraction. The best way to end the day is by taking a stroll along the coastal banks.
Easton, Maryland
Located on the Eastern Shore, Easton, Maryland, is known for its outdoor activities and live annual festivals, like the famous Crab Drop on New Year's Eve. Another famed event is the Waterfowl Festival, which celebrates local culture with art, food, music, and more in November. Easton is also home to numerous landmarks and commercial structures, like the Tidewater Inn. The inn dates back to the 19th century, has comfortable accommodations, and is home to Hunter’s Tavern, perfect for a nightcap. For a different take on local heritage, Frederick Douglas is a monumental figure throughout town, commemorated in a bronze statue downtown. There are guided driving tours that showcase this American hero's home shores.
Cambridge, Maryland
Cambridge was founded in 1684 on the banks of the Choptank River and is one of the oldest colonial settlements in the U.S.. One of the town's most historical figures is Harriet Tubman, one of the greatest American heroes. The Bucktown Store, where the Civil Rights icon made her first public acts of defiance, is still a must-see travel destination.
Many other sites in town commemorate Harriet Tubman, like the Underground Railway Center and the Underground Scenic Byway. The town's 19th-century history merges beautifully with its rich maritime history. Richardson Maritime Museum highlights this history with exhibits and docent-guided tours. Don't forget to stop by Ruark Boatworks for a romantic voyage on the sailing ship Nathan of Dorchester.
Wrapping Up
The isolated towns around the Chesapeake Bay have a unique charm and character that is hard to overlook when seeking a coastal destination. Quintessential towns like Havre de Grace and St. Michaels display the landmark walkable towns and beautiful architecture for which the area is known. Towns like Tappahannock, Virginia, are filled with historical significance set against a scenic background of the bay and Rappahannock River.
One of the best things about visiting small villages and hamlets is the lack of crowds. This is evident in these nine towns, which allows you more time to soak in the town's nature. The coastal atmosphere, friendly communities, and excellent restaurants are just a few attributes that make these towns unique.
