Part of St. Michaels Harbor in historic Saint Michaels, Maryland

8 Cozy Towns To Visit In Chesapeake Bay

Chesapeake Bay, the largest estuary in the United States, spans over 200 miles from Maryland to Virginia. Covering an area of approximately 4,479 mi2, it is fed by over 150 rivers and streams. The bay's watershed includes parts of six states and Washington, DC, supporting a diverse range of ecosystems and providing critical habitats for various species of fish, birds, and other wildlife. Chesapeake Bay is home to numerous cozy towns characterized by their picturesque waterfronts, boutique local shops, and welcoming community atmospheres. These eight cozy towns on the bay should be on your travel list.

St. Michaels, Maryland

Aerial view of St. Michaels, Maryland
Aerial view of St. Michaels, Maryland.

St. Michaels, located on Maryland's Eastern Shore, is a town with a deep-rooted maritime history. Founded in the 17th century, it became a shipbuilding center and trading port. The town's location along the Miles River and the Chesapeake Bay made it a spot for commerce and transportation. Today, St. Michaels is known for its waterfront and historic homes.

Chesapeake Bay Maritime Museum has exhibits on the maritime history of the Chesapeake Bay. Visitors can explore the museum's collection of historic boats and maritime artifacts. Hooper Strait Lighthouse, located on the museum grounds, is a historic lighthouse that has guided tours. It provides insights into the life of lighthouse keepers and the history of Chesapeake Bay navigation. Tilghman Island has views and a glimpse into local watermen's culture. The island is known for its working waterfront and traditional seafood industry.

Cambridge, Maryland

Marina in Cambridge, Maryland.
Marina in Cambridge, Maryland.

Cambridge, one of the oldest towns in Maryland, was established in 1684. Located on the Choptank River, it became a significant port and trading center. The town's history includes its role in the Underground Railroad and the life of Harriet Tubman, who was born nearby.

The Harriet Tubman Underground Railroad Visitor Center is dedicated to the life of Harriet Tubman and the Underground Railroad. Visitors can learn about her courageous efforts and the history of the Underground Railroad through exhibits and educational programs. Blackwater National Wildlife Refuge has kayaking, birdwatching, and nature trails. The refuge is home to diverse wildlife and provides opportunities for outdoor recreation. Choptank River Lighthouse is a replica of a historic lighthouse with views. It is a symbol of the town's maritime heritage and has educational exhibits.

Oxford, Maryland

Boats in the harbor of Oxford, Maryland
Boats in the harbor of Oxford, Maryland.

Oxford, founded in 1683, is another one of Maryland's oldest towns. Situated along the Tred Avon River, it became a bustling port town in the colonial era. Oxford's maritime history is evident in its historic homes, waterfront, and active boatyards. The town's tranquil atmosphere and scenic beauty make it a popular destination for visitors seeking a peaceful retreat.

Oxford-Bellevue Ferry is one of the oldest operating ferries in the United States. It provides a scenic crossing of the Tred Avon River and connects the towns of Oxford and Bellevue. Oxford Museum has exhibits on the town's history and heritage. Visitors can explore artifacts and stories that highlight Oxford's maritime and cultural past. Chesapeake Bay Environmental Center is home to trails and educational programs. The center focuses on environmental conservation and has opportunities for birdwatching and nature study.

North Beach, Maryland

 Homes on the Chesapeake Bay, in North Beach, Maryland.
Homes on the Chesapeake Bay in North Beach, Maryland.

North Beach, located on the western shore of the Chesapeake Bay, was established in the early 20th century as a resort town. Known for its sandy beaches and boardwalk, North Beach quickly became a popular vacation destination. The town's proximity to Washington, D.C., and Baltimore made it an accessible getaway for urban residents.

North Beach Boardwalk is a walkway along the Chesapeake Bay. Visitors can enjoy waterfront views, local shops, and eateries along the boardwalk. Bayside History Museum has exhibits on the local history of the Chesapeake Bay area. The museum provides insights into the town's development and cultural heritage. Wetlands Overlook Park is a natural area with trails and birdwatching. The park is a peaceful retreat for wildlife observers.

    Easton, Maryland

    Easton, Maryland
    The intersection of Dover and Washington Streets in Easton, Maryland.

    Easton, located in Talbot County, was founded in 1710 and was a center of government and commerce on Maryland's Eastern Shore. The town's historic district has well-preserved 18th and 19th-century buildings. Easton's arts scene, cultural institutions, and annual festivals make it a lively community.

    Pickering Creek Audubon Center has trails and birdwatching opportunities. The center is dedicated to environmental education and conservation, with programs for all ages. Avalon Theatre is a historic theatre hosting live performances and events. It is a cultural hub for the community, with a range of musical, theatrical, and film events. The Academy Art Museum has art exhibits and educational programs. The museum showcases works by regional and national artists and offers classes and workshops.

    Solomons, Maryland

    Drum Point Lighthouse in Solomons, Maryland
    Drum Point Lighthouse in Solomons, Maryland. Editorial credit: Malachi Jacobs /

    Solomons, located at the southern tip of Calvert County, is a waterfront town. Established in the late 19th century, it grew as a center for shipbuilding, fishing, and oyster harvesting. Solomons' setting along the Patuxent River and Chesapeake Bay, combined with its cultural and recreational attractions, make it a tourist destination.

    Calvert Marine Museum hosts exhibits on marine life and local history. The museum includes an aquarium, paleontology exhibits, and maritime artifacts. Drum Point Lighthouse, located at the museum, is a historic lighthouse that provides tours and educational programs. Visitors can learn about the history of fishing and sailing in Chesapeake Bay here. Annmarie Sculpture Garden & Arts Center has art exhibits and nature trails. The center hosts a variety of art installations, classes, and community events.

    Onancock, Virginia

    Sailboat in the marina at the center of Onancock, Virginia
    Sailboat in the marina at the center of Onancock, Virginia. Editorial credit: MargJohnsonVA /

    Onancock, located on Virginia's Eastern Shore, is a town with roots dating back to the 17th century. Initially established as a port and trading center, Onancock grew into an important destination for commerce and transportation. The town's has well-preserved architecture and a waterfront location.

    Ker Place is a historic house museum showcasing 18th-century life. The museum hosts guided tours that detail the architecture and history of the period. Onancock Creek is for kayaking and scenic views. The creek is a spot for water activities. Tangier Island, accessible by boat, is known for its culture and history. Visitors can experience the island's distinctive way of life and learn about its maritime traditions.

    Cape Charles, Virginia

    Aerial View of Beach Homes in Cape Charles Virginia
    Aerial view of beach homes in Cape Charles, Virginia.

    Cape Charles, located on the southern tip of Virginia's Eastern Shore, was founded in the late 19th century as a planned community for the railroad industry. The town was a transportation destination for passengers and goods traveling between the Eastern Shore and Norfolk.

    Kiptopeke State Park is known for its birdwatching, fishing, and unique concrete ship breakwaters. The park has opportunities for outdoor activities and nature observation. Savage Neck Dunes Natural Area Preserve is home to trails, dunes, and beaches. The preserve is a protected area that showcases the region's natural coastal habitat. Chesapeake Bay Bridge-Tunnel is an engineering feat with views of the bay. The bridge tunnel connects the Eastern Shore with the mainland.

    The Chesapeake Bay features a variety of cozy towns that embody the region's charm and history. With its quaint streets and maritime heritage, St. Michaels invites visitors to explore its local shops and scenic waterfront. Cambridge has a warm community atmosphere and insights into the life of Harriet Tubman, along with nature reserves. Meanwhile, Oxford brings a sense of peace with its historic ferry and waterfront. These eight towns collectively highlight the cozy nature of the Chesapeake Bay area, making them perfect destinations for a getaway.

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