Aerial panorama of shipyard and lighthouse in St. Michaels harbor in Maryland.

11 Most Underrated Towns Along The Chesapeake Bay

Chesapeake Bay is the largest estuary in the United States and is located in the Mid-Atlantic region. It covers the eastern shores of Maryland and Virginia. The area is known for blue crabs, maritime history, a large abundance of waterfowl, and many different types of fauna.

The small waterfront towns that comprise the area welcome visitors and offer many historical sites and modern amenities. Because of the fantastic weather, it is a popular destination for travelers, especially during the Spring and Fall. These eleven towns are sometimes overlooked but have plenty of outdoor activities, charming museums, and historical sites that make them unique and fun.

Onancock, Virginia

The historical Williams House, Onancock, Virginia.
The historical Williams House, Onancock, Virginia. Image credit: Joel Abroad via

Onancock is a small coastal town in Virginia founded in the early 1600s. Though the town has a population of less than 2,000, it is considered a town with heart and has a vintage movie theatre with an annual International Film Festival. The charming town is also known for its art scene, which includes several galleries, including the Red Queen and Danny Doughty. There is also a collection of local glass blowers and a performing arts theatre, the North Street Playhouse.

Onancock also has gorgeous natural scenery, which is unsurprising for this area. The Tangier Ferry and the Onancock Sailing Adventures are popular sites for those looking for a fun time on the water. There is a maritime museum celebrating the town's history, Deltaville Maritime Museum, and one celebrating the history on shore, Ker Place.

Cape Charles, Virginia

The Cape Charles Beach on the Chesapeake Bay, in Cape Charles, Northampton County, Virginia
The Cape Charles Beach on the Chesapeake Bay, in Cape Charles, Virginia.

Cape Charles is a historic town in Virginia that boasts the largest collection of early 20th-century architecture on the East Coast. Peach Street Books is a favorite among locals and tourists and a popular Instagrammable bookstore. There are also quaint museums and art galleries, like the Cape Charles Museum and the Ellen Moore Gallery.

The Cape Charles Natural Area Preserve is 50 acres of outdoor activities and is perfect for a lazy stroll. The boardwalk has been well maintained and winds through beautiful scenery. Hotel Cape Charles is an impressive two-star, two-story, brick hotel. It is boutique-style and encompasses the spirit of Cape Charle, which is perfect for a short stay in this remarkable town.

Urbanna, Virginia

Urbanna Creek, Urbanna Virginia
Urbanna Creek, Urbanna Virginia. Image credit: Watts via

Urbanna, Virginia, is a quaint and friendly town with colonial homes, a walkable downtown area, and more boats than people. The name Urbanna means City of Anne, and the town was named for Queen Anne. The other claim to fame is that it is home to Virginia's annual oyster festival, where local chefs, boaters, and other residents help the visitors shuck the oysters.

The Urbanna Museum and Visitor Center is a great spot to learn about the area and its history. The locals are warm and can also provide all the information you need. The best way to see Urbanna is on foot. If you are walking around town, stop at Taber Park to check out the "LOVE" sign. You can even rent it for special occasions, making it a great photo opportunity.

Irvington, Virginia

Carter's Creek in Irvington, Virginia
Carter's Creek in Irvington, Virginia. Image credit: Panoramio via Wikimedia Commons.

Irvington, Virginia, on the Northern Neck Peninsula, is a designated historic town with beautiful natural scenery. One of the most unique places to explore is the Steamboat Era Museum, which provides great local history. There are also beautiful natural expanses like Carter's Creek, where people can observe eagles, ospreys, and herons.

This rustic village has amazing dining and lodging options. The Dog and Oyster Micro Winery and Oyster Bar is a popular restaurant with outdoor seating that attaches to a luxurious inn. The Tides Inn is a four-star inn with a restaurant that gets high reviews and will elevate your experience in Irving.

Havre de Grace, Maryland

Havre de Grace, Maryland
The lighthouse at Havre de Grace, Maryland.

Havre de Grace, Maryland, or HdG for short, is located at the mouth of the Susquehanna River and the head of Chesapeake Bay. It was named for the port city in France and is today known as a friendly town with plenty of things to do. One of the most fun things to do is First Fridays, when the downtown streets close down and draw a family-friendly crowd. There is live music, food trucks, and local artisans selling their wares.

Other popular sites include the Friends-Concord Pointe Lighthouse and the Havre de Grace Maritime Museum, both of which highlight the maritime history of this coastal town. Another interesting museum is the Lock House, originally an 1840s riverfront mansion. Several antique mansions have been converted into museums, making this small community even more remarkable.

Saint Michaels, Maryland

Aerial view of Saint Michaels, Maryland.
Aerial view of Saint Michaels, Maryland.

Saint Michaels, Maryland, was once a hub for shipbuilding and oystering and is now a destination for boaters, water enthusiasts, and outdoor lovers. It is also home to the historic landmark, the 1879 Hooper Strait Lighthouse, which is available for tours. The Saint Michaels museum, a converted home from the 1840s, adds an amount of nostalgia to this quaint seaside town.

Another fun visit in Saint Michaels is the Classic Motor Museum, which hosts several events, such as Cars and Coffee, on select days. The best way to see this town is at a slower pace. The Wildest Hotel is on the main drag, Talbot Street, and offers accessible trips on foot to the hub of the restaurants and shops. Also on Talbot is St. Michaels Winery, which is a pleasant way to wind down a day of sightseeing.

Easton, Maryland

The Talbot County Courthouse, in Easton, Maryland.
The Talbot County Courthouse, in Easton, Maryland.

Easton is a Main Street Community on the Eastern Shore of Maryland known for its pleasant aesthetic. Since its founding in 1790, it has been known as the Sophisticated Center of the Eastern Shore. Spring is a great time to visit when the flowers and trees bloom, perfect for a trip through historic downtown.

Some sites to see downtown include the Frederick Douglass statue in front of the brick courthouse and the Academy Art Museum, one of many galleries in this artist's retreat. There are also many Victorian bed and breakfasts and historic inns to lodge in, including the Waterfront and the Tidewater Inn. Easton is one of the most culturally significant towns on the Chesapeake Bay and should not be overlooked when visiting this area.

Solomons Island, Maryland

Solomons Island, Maryland.
Solomons Island, Maryland.

Solomons Island, Maryland, also known as Solomons, is convenient to Baltimore and is a fun weekend retreat, especially in the warmer months. One such fun attraction is the Annmarie Sculpture Garden and Art Center, which includes a sprawling park. If you are enjoying the weather, visit Drum Point Lighthouse. It is one of only four surviving Chesapeake Bay screw-pile lighthouses and used to look out over the entrance of the Patuxent River. Now, it is an exhibit at the Calvert Marine Museum.

A fun way to explore the island is by embarking on a Tiki Tour. These floating, thatch-roofed floats provide gorgeous scenery and a relaxing atmosphere. Solomons has long been considered a natural paradise for its beautiful water and various biodiversity of plant and fauna species.

Chesapeake City, Maryland

Chesapeake City along the Chesapeake and Delaware Canal
Chesapeake City along the Chesapeake and Delaware Canal in Maryland. Image credit: Jennifer Schmidt via Wikimedia Commons.

Chesapeake City, Maryland, was originally named by a Bohemian colonist as The Village of Bohemia. The name was changed in 1839 after the Chesapeake and Delaware Canals were built. Today, it is the only town in Maryland on a working commercial canal.

Most Victorian architecture has remained intact, so the town is registered as a historic place. There are many sites to discover here, including the Chesapeake City Bridge, Mount Felix Vineyard and Winery, and the Historic District. The C&D Canal Museum is an ideal way to understand just how important these waterways are and the importance of the canal system.

Cambridge, Maryland

The marina at Cambridge, Maryland.
The marina at Cambridge, Maryland.

Cambridge, Maryland, is famous for being a stop along the Underground Railway. There was a large network of safe houses, many of which still exist today. There is a Harriet Tubman museum where visitors can explore her fascinating life and why this town was important for her mission. The town also developed many food processing industries, including canning oysters and sweet potatoes.

Maritime history buffs are encouraged to visit the Choptank River Lighthouse and the Richardson Maritime Museum to learn about the Chesapeake Bay's long and storied maritime history. As with all Chesapeake Bay towns, there is plenty for the nature lover to do, too. The Blackwater National Wildlife Refuge, established in 1933, is a popular wildlife sanctuary among bird watchers. The 5,000-acre refuge is a popular resting area for birds along the Flyway and is a unique way to see the natural beauty of the Eastern Shore.

Rock Hall, Maryland

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

Rock Hall, Maryland, is a tiny waterfront town on the National Chesapeake Scenic Byway. Main Street was the first road built in Maryland in 1675, just a small part of its history. Rock Hall is an authentic Chesapeake Bay fishing village with "Nice People Live Here" written on its welcome sign.

Outdoor activities like boating and fishing are popular here, but there are also three free museums and chilled-out waterfront bars and restaurants. The museums are the Rock Hall Museum, the Waterman's Museum, and the Tolchester Beach Revisited Museum Revisited. After seeing the Old Salt statue on Main Street, head to one of the waterfront restaurants like The Rock or The Shack.

The Eastern Shore, where the Chesapeake Bay is located, is a gorgeous part of the country with amazing maritime and American history. These eleven towns offer amazing glimpses of what "the Bay" offers. From natural preserves to historic lighthouses to pre-18th century homes, there is something here for everyone.

What these towns share in common is that they all have small populations, but visitors do not get bored here. There is just too much to see and do. Unless, of course, you want to take a Tike Tour around Solomons and go at a slower pace. Most of these towns are easily walkable, a great way to soak in these historic towns' coastal atmospheres.

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