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Both spans of the bridge stretching miles across the Chesapeake Bay

Place

Chesapeake Bay Bridge at Kent Island

US 50/301 at Kent Island Stevensville, MD 21666

The Chesapeake Bay Bridge at Kent Island is Maryland’s great threshold between the Western Shore and the Eastern Shore. Officially the William Preston Lane Jr. Memorial Bridge, the dual-span US 50/301 crossing links Sandy Point near Annapolis with Stevensville on Kent Island and reshaped travel, tourism, commuting, and local life across the Chesapeake.

View of the public boat ramp area at Secretary Boat Ramp in Secretary, Maryland.

Place

Secretary Boat Ramp

Near Temple Street and Second Street Secretary, MD 21664

Secretary Boat Ramp is a public boat landing on the Warwick River in Secretary, Maryland. Tucked into one of Dorchester County’s small waterfront towns, the ramp offers practical access for boaters, anglers, paddlers, and anyone who wants to understand how closely daily life on the Eastern Shore is tied to its creeks and rivers.

Storefront of Dorchester Pizza in Secretary, Maryland, with a green awning, a crab holding a pizza slice on the sign, an open sign, and a banner advertising happy hour specials.

Place

Dorchester Pizza

107 Main Street Secretary, MD 21664

Dorchester Pizza is a small-town pizzeria on Main Street in Secretary, Maryland, serving pizza, pasta, subs, wings, salads, and other casual meals from the heart of town. In a place as small as Secretary, a Main Street pizza shop is more than a menu — it is part of the everyday local fabric.