Chesapeake Country Scenic Byway

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

Colorful houses on the Susquehanna waterfront
A lovely town on the water, Chesapeake City, Maryland (Photo Credit: Clark Vandergrift, courtesy Maryland Office of Tourism Development)
Inn at Perry Cabin, St. Michael's, Maryland
Chesapeake Bay Maritime Museum, St. Michaels, Maryland
Kayaking on Maryland's Eastern Shore
Kayaking adventures near Cambridge, Maryland
Crab feast at the Crab Claw Restaurant, St. Michaels, Maryland
Colorful houses on the Susquehanna waterfront
Kayaking on Maryland's Eastern Shore

Your 1st Day: Chesapeake Culture, Beaches & Boating

Chesapeake City 

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

Betterton 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

“Our Chesapeake Legacy”, an interactive, hands-on exhibit provides an overview of the region’s heritage, resources and culture while exploring the relationship of man and the bay.

Your 2nd Day: Small Towns, Family Fun & Nature Excursions


One of the best small towns in America. Visit the Academy Art Museum, historic Quaker meeting house and stroll the streets lined with elegant Victorian homes, boutiques and tempting restaurants.

St. Michaels

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


This historic waterfront community 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.

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