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, Couple, Chesapeake Bay, Maryland
Relax on sandy beaches at waterfront towns along Maryland's Eastern Shore.
Inn at Perry Cabin, sailboat, Miles River, St. Michaels
Inn at Perry Cabin, St. Michael's, Maryland
Choptank River Lighthouse, Maryland
Choptank River Lighthouse in Cambridge, Maryland
cycling, chesapeake, maryland, trail, Queen Anne's County
Cycling the Cross Island Trail
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Kayaking on Maryland's Eastern Shore
Beach, Kent Island, Couple, Chesapeake Bay, Maryland
Inn at Perry Cabin, sailboat, Miles River, St. Michaels
Choptank River Lighthouse, Maryland
cycling, chesapeake, maryland, trail, Queen Anne's County
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Chesapeake Country Scenic Byway is a designated All-American Road.

The most exceptional driving tours are scenic byways that have been designated All-American Roads by the Federal Highway Administration. These byways feature nationally significant archaeological, cultural, historic, natural, recreational, and scenic qualities that you will not find elsewhere in the United States.

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.

Mount Harmon Plantation and Nature Preserve

This former tobacco plantation is the northern most colonial-era Tidewater Plantation in the Chesapeake Region. Listed on the National Register of Historic Places, admission to the site includes a guided tour of the manor house and plantation kitchen. Visitors can also tour the gardens, grounds, and nature trails.

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.

Eastern Neck National Wildlife Refuge

This 2,285-acre wildlife refuge in Kent County provides a habitat for thousands of wintering waterfowl including the tundra swan. The refuge is home to 234 species of birds and features nature trails, observation decks, and picnic areas.


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. A large portion of downtown Chestertown is designated an official Historic District and a National Historic Landmark, second only to Annapolis in the number of Colonial era buildings. 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. Start your journey at the Chesapeake Heritage & Visitors Center.  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

Kent Narrows

Start your day along the scenic Kent Narrows waterfront. The Kent Narrows waterway connects the Chester River and Eastern Bay. Take a walk or rent a bike to cycle the Cross Island Trail, a 6.5-mile trail along an abandoned railroad corridor, from Terrapin Park to Kent Narrows. The trails features stunning views of the Chester River as it passes through farmlands, meadows and woods.

Kent Narrows is also a great place to charter a boat for exploring the Captain John Smith Chesapeake National Historic Trail and the Maryland system of water trails. Maryland has more than 750 miles of designated water trails. The trails follow the region’s rivers, from the Patuxent to the Potomac, as they feed into the Chesapeake Bay. Between 1607-1609, Captain John Smith and crew mapped nearly 3,000 miles of the Chesapeake Bay and its tributaries. Today, visitors can kayak, canoe or sail several water trails following Smith’s path and learn more about John Smith’s Chesapeake touring the many sites along the Chesapeake Bay.

Old Wye Grist Mill and Museum

Built in 1682, Old Wye is the oldest continuously operated water powered grist mill in the US. The mill produced flour for General George Washington’s troops during the American Revolution. Today, visitors can watch the mill at work during their bimonthly grindings hosted on the first and third Saturdays, tour the mill, and purchase grains, flours, and other local goods at the mill’s gift shop.


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. In town, Long Wharf Park is located on the Choptank River and offers fishing piers, waterfront views, picnic tables, and historic attractions. Here visitors will find the skipjack Nathan of Dorchester, the Cambridge Marina, and the Choptank River Lighthouse.

Day 3: Historic Sites and Nature Preserves

Pemberton Historical Park

This 262-acre historical park in Salisbury, Maryland offers 4.5 miles of nature trails across the different ecosystems that encompass the Eastern Shore. On Saturdays from May-October, visitors can also tour the 18th century Pemberton Hall, home of Colonel Isaac Handy and his wife Anne.

Delmarva Discovery Museum

The Delmarva Peninsula, formed by Delaware and parts of the Eastern Shores of Maryland and Virginia, is a 170-mile long peninsula occupying the landscape between the Chesapeake Bay and the Atlantic Ocean. The Delmarva Discovery Museum seeks to explore the relationship between this unique environment and its inhabitants. The museum features hands-on and interactive exhibits including river otters and touch pools.

Smith Island

A short ferry ride from the town of Crisfield, Smith Island is famous for its layered cakes (the Smith Island Cake is the official dessert of Maryland) and for being the hub of the soft-shell crab industry in the US. The island is also known for its outdoor recreation. The shallow waters surrounding the island are ideal for fishing and kayaking. Back on land, residents and visitors alike travel the island by golf cart, bicycle, and on foot.

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

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