Chesapeake Country Scenic Byway in Maryland

Experience the special landscapes of Maryland's tidewater region and gain an appreciation for the working life of Eastern Shore farmers, watermen and merchants.

Kayaking on Maryland's Eastern Shore
Kayaking adventures near Cambridge, Maryland
Beach, Kent Island, Queen Anne's, Maryland
Relax on sandy beaches at waterfront towns along Maryland's Eastern Shore. (Photo courtesy Jay Fleming)
Inn at Perry Cabin, sailboat, Miles River, St. Michaels
Inn at Perry Cabin, St. Michael's, Maryland
Kayaking on Maryland's Eastern Shore
Beach, Kent Island, Queen Anne's, Maryland
Inn at Perry Cabin, sailboat, Miles River, St. Michaels

Day 1: Chesapeake Culture, Beaches & Boating

Chesapeake City 

Chesapeake City is located along the historic Chesapeake and Delaware Canal connecting the Chesapeake Bay with the Delaware River. Visit the Chesapeake & Delaware Canal Museum, which recounts the history of the building of the 14-mile canal, one of only two commercially vital sea-level canals in the US.

Betterton Beach

The tow of Betterton, Maryland emerged in the 1700s as a small fishing village. Today this five-acre, landscaped, family-oriented waterfront park has an exceptional sandy beach with 300 feet of frontage for swimming and 700 feet of shoreline access.

Rock Hall

Rock Hall is known as the “Pearl of the Chesapeake." Charter a boat, eat fresh seafood, sit on a Chesapeake Bay beach or visit the Watermen’s Museum at Haven Harbour Marina.


Located along the banks of the Chester River, Chestertown provides a link to the maritime heritage of the Chesapeake Bay. It is home to the Schooner Sultana and a thriving colonial historic district. The historic buildings are the backdrop for visitors who enjoy ambling along red-brick sidewalks, peeking over garden walls and exploring antique shops, galleries, specialty stores and sidewalk cafes.

Chesapeake Exploration Center

At the Chesapeake Exploration Center in Chester, don't miss “Our Chesapeake Legacy,” an interactive, hands-on exhibit that provides an overview of the region’s heritage, resources and culture while exploring the relationship of man and the bay.


Day 2: Small Towns, Family Fun & Nature Excursions


Visit one of the "Best Small Towns in America" in Easton to check out the Academy Art Museum and historic Quaker meeting house, then stroll streets lined with elegant Victorian homes, boutiques and tempting restaurants.

St. Michaels

Explore the Chesapeake Bay Maritime Museum in St. Michaels, featuring a working boatyard, hands-on activities for kids and a restored 1879 lighthouse. Dine on crab cakes overlooking the harbour and then relax at the Linden Spa at the Inn at Perry Cabin.


The historic waterfront community of Cambridge offers skipjack sailing cruises and boat tours, and is a good home-base to explore the nearby Blackwater National Wildlife Refuge, home to the largest nesting population of bald eagles on the US East Coast.

Scenic Drives
Wine & Cuisine
History & Culture
Attractions & Family Fun

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