Gems Along the Chesapeake Bay’s Eastern Shore

We have all heard about the Eastern Shore. Area natives, especially, know it as a conglomeration of vacation destinations along the eastern side of the Chesapeake Bay. Tourist spots. Fishing villages. Colonial towns. Communities that thrive in the summer months but are deserted for the rest of the year. While there might be truth to some of these notions, there is infinitely more to say about the diverse areas of Maryland and Virginia that constitute this collective waterfront region.

The Eastern Shore is composed of distinct locales, which house residents and host visitors with their inimitable personalities. They are undoubtedly recognized for their summer appeal but should not be completely discounted leading up to the heat. Many of these towns are celebrated for their historical significance, tranquil quality and distinguishing identity – you should consider exploring some of them in the coming months.

Featured towns: Eastern Shore, Md.

This colonial town on the Chester River entices travelers to experience its historic homes, shops, arts scene and restaurants. As part of Kent County, it is surrounded by the Chesapeake Bay’s estuaries and farmland, and holds annual events and holiday functions throughout the year.
Chestertown is also home base to the Schooner Sultana, “a replica of a Boston-built merchant vessel that served four years as the smallest schooner ever in the British Royal Navy,” according to its website. The ship is known as the “Schoolship of the Chesapeake,” as it offers educational programming through sailing tours.
The Chestertown website offers additional suggestions for visitors, including self-guided tours, museums, theaters, scenic views and recreational activities. There are more than 40 lodging options in the vicinity, though it is known for its bed and breakfasts.

You are likely familiar with St. Michaels, as its Bay presence has become less subtle over time, and it is now better known for its tourist draw. Its marina and boating opportunities contribute to its charm, but St. Michaels is equally beloved for its memorable attractions, dining, spas and special events.
The Chesapeake Bay Maritime Museum, the St. Michaels Winery, War of 1812 reenactments, the St. Michaels Fresh Farm Market, various cruise lines and fresh seafood meals are among the services that continue to bring visitors to the area. Vacation rentals and quaint hotels provide an array of lodging alternatives, and the website’s suggested itineraries aid with planning the ideal vacation.

This seaside village invites people to discover its character year-round. In addition to crabbing, sailing, kayaking and canoeing, Easton is a relaxing town with outlets for exploration and enjoyment – despite the weather. Its buildings represent a fusion of Colonial and Victorian architecture, and the town is renowned for its displayed appreciation of art and music. The Avalon Theatre presents comedy, art shows, theatrical performances and assorted concerts that make it a staple venue for both vacationers and locals.
Antiquing in downtown Easton, stargazing in the countryside and watching wildlife are just some of the many activities highlighted on the website. Other components of a visit might involve walking tours, community coffee shops, public golf courses, annual festivals and Victorian bed and breakfasts. An events calendar, which consistently outlines a plethora of activities for tourists, can be found on the website.

Situated on the Choptank River is Cambridge: it was settled in 1684, and is now one of the Eastern Shore’s prime destinations. The historic downtown, centered around Cambridge’s Main Street, is more than “beautiful buildings” and “one-of-a-kind shops,” as the downtown touts itself. Rather, it has a powerful presence that stems from its rich history and is apparent to any visitor.
Quirky celebrations add another dimension to the pulse: “Zip Code Day,” “Taste of Cambridge Crab Cook-Off” and “Summer Send-Off: Blues, Brews & BBQ,” to name a few.
Cambridge is home to several noteworthy attractions – the Brannock Maritime Museum, the Richardson Maritime Museum and La Grange Plantation – and other galleries, boutiques and art districts. Great Marsh Park, Sailwinds Park and the Choptank River Fishing Pier are other area favorites.

Featured Towns: Eastern Shore, Va.

As the County Seat of Accomack County, this small but significant town attracts people with its history and charm. It was originally established as the Town of Drummond in 1786 and, subsequently, Drummondtown. It did not receive its present name until 1893.
One of Accomac’s strongest tourist draws is perhaps its walking tour, during which people can gain understanding of the town’s evolution, through architectural changes in churches, cottages and houses. The Eastern Shore Public Library, Debtor’s Prison, Bloodworth Cottage and St. James Episcopal Church are among the notable points on the downtown tour. People live in the private residences, illustrating the community’s intimate nature and appreciation for historic preservation.

Originally serving as a port town, Onancock aided transportation for steamboats between Baltimore, Md., and Norfolk, Va., with the Onancock Creek leading to the Bay. It is now one of the Eastern Shore’s more heavily populated towns, with more than 1,500 residents.
Onancock has substantial marine- and wild- life populations and water travel opportunities. Whether you bring your own boat, take a guided trip or just want to get a full taste of Onancock, the Town Wharf is a must-see. And, the Ferry to Tangier Island, a nearby fishing village, lets visitors venture beyond the town.
As a self-described “rural waterfront village,” Onancock’s visitor-friendly atmosphere and easily navigated downtown make it a desirable spot for tourists who enjoy biking and strolling. More information is listed on its website.

Wachapreague is an appropriately named seaside town – its website defines “Wachapreague” as “Little City by the Sea.” Bird watching and biking keep people coming throughout the year, as do the fishing and seafood.
The Hotel Wachapreague, the town’s first hotel and one of the largest on the Eastern Shore, was constructed in 1902 and remains open today. A marine railroad and commercial fishing are some of the many draws to this charming fishing community. ([].

Cape Charles has a history that dates back to the 1880s. Following its colonization, it was predominantly comprised of farmlands and wetlands, but as stated on its website, it developed into a railroad region when the Bay Coast Railroad was constructed. It is the largest town in Northampton County with 1,000 residents and under 3,000 acres of land.
The Historic District of Cape Charles displays a variety of architecture, including Colonial Revival, Neoclassical and Victorian style homes. Golf clubs, horseback riding stables, wildlife refuges, state parks – plus the water, beaches and fishing – make this town a great place to investigate. [](

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