Chesapeake Country

Take your time experiencing the special beauty of this tidewater region with its pristine waterways and vibrant historic waterfront villages.

Prior to the 1890s, Chestertown's Fountain Park was home to the town's market house and armory.

Eastern Shore
419 miles from Chesapeake City to Crisfield on country roads along the bay's edge and part of the Great Chesapeake Bay Loop.

Places along the way

C&D Canal Museum (1837)
815 Bethel Rd
Chesapeake City, MD 21915

Crystal Beach
88 Bay Blvd
Stevensville, MD 21666

Mount Harmon Plantation
600 Mount Harmon Rd
Earleville, MD 21919

Kitty Knight
14028 Augustine Herman Hwy
Georgetown, MD 21930

Kent Museum
13685 Turners Creek Rd
Kennedyville, MD 21645

Crow Vineyard and Winery
12441 Vansant Corner Rd
Kennedyville, MD 21645

Eastern Neck National Wildlife Refuge
1730 Eastern Neck Rd
Rock Hall, MD 21661

Museum of Eastern Shore Life
120 Dulin Clark Rd
Centreville, MD 21617

Queenstown Premium Outlets
441 Outlet Center Dr
Queenstown, MD 21658

Avalon Theatre
40 E Dover St
Easton, MD 21601

Chesapeake Bay Maritime Museum
213 N. Talbot St
St. Michaels, MD 21663

Tilghman Island
US 322 to Rt 33
Tilghman, MD 21671

Oxford Museum
101 S. Morris St
Oxford, MD 21654

Richardson Maritime Museum
401 High St
Cambridge, MD 21613

Blackwater National Wildlife Refuge
2145 Key Wallace Dr
Cambridge, MD 21613

Ward Museum of Wildfowl Art, Salisbury University
909 S Schumaker Dr
Salisbury, MD 21804

Teackle Mansion
11736 Mansion St
Princess Anne, MD 21853

Janes Island State Park
26280 Alfred J. Lawson Dr
Crisfield, MD 21817

The lifestyles and livelihoods of generations of watermen, shipbuilders and farmers have been shaped by an unspoiled landscape that, even to this day, makes it easy for visitors to imagine earlier times when goods were shipped to “faraway Baltimore” in wooden barrels lashed aboard schooners. The pace of life is slower here. Charming small towns are often accessed by boat as well as car. Popular pursuits include biking, kayaking, enjoying the cultural scene in arts communities and dining on some of the nation’s best seafood.  Travel this byway to explore the Great Chesapeake Bay Loop, your key to Chesapeake adventures.

Upper Eastern Shore section from Chesapeake City to Kent Island

Including MD 213 & MD 18

From Chesapeake City, you can look out over the 14-mile-long Chesapeake and Delaware Canal to see modern-day ships dwarfing Victorian homes and shops along the banks. The C&D Canal Museum captures the history of the 165-year-old waterway.

Head south along winding roads that lead past spectacular scenery. Then, as you enter Cecilton, plan a stop at Crystal Beach, a summer town on the Elk River that is popular with swimmers and anglers. Nearby is the Stemmers Run Managed Hunting Area, which, outside of hunting season, is known for its hiking and fishing.

A side trip reveals the graceful beauty of Mount Harmon Plantation in Earleville. This 200-acre Colonial plantation, featuring an antiques-filled manor house museum and walking trails, is on a peninsula surrounded by the Sassafras River.

Across the river is Georgetown, which the British burned during the War of 1812 but has been rebuilt and is a popular place for dining and entertainment. Continue toward Galena and on to Kennedyville, where you will find Crow Farm Vineyard and Winery. Stop at the Kent Museum to see displays of antique tractors, horse-drawn sleds and household equipment.

Sidetrack to the town of Betterton, a beach resort that still boasts fine examples of Victorian-era architecture. Back on the byway, farms glide by as you head to Chestertown, a Colonial port that is home to Washington College, founded in 1782 and named for its patron, George Washington. Among the elegant brick town homes in the city’s historic district you can enjoy concerts in the square.

Veer west to Rock Hall, which has more than a dozen marinas offering mooring and charter services. The town also prides itself on excellent seafood dining, a homemade ice cream shop and a small, maritime-oriented museum. The Eastern Neck National Wildlife Refuge, an isolated ecosystem with nesting bald eagles and extensive hiking trails, is just to the south.

The area that extends from Chestertown through Centreville and into Queenstown is famous for its large number of fine antiques shops. But you can also find bargains on name-brand items at Premium Outlets. Along the way, make a stop at the Museum of Eastern Shore Life to admire an eclectic collection of artifacts ranging from a log canoe to early hand tools.

Grasonville invites you to get back to nature at an environmental center surrounded by prime hiking, canoeing and birdwatching trails. Then stretch your legs some more after crossing over to Kent Island, where the Cross Island Trail extends for six miles from Terrapin Nature Park to the Kent Narrows.

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The Chesapeake Bay Maritime Museum in St. Michaels includes a working boatyard that aims to pass fading maritime skills on to a new generation of shipwrights as well as a number of great exhibits.

Image Credit: Chesapeake Bay Maritime Museum

Mid-Shore section from Wye Mills to Vienna

Including US 50, MD 331 & MD 313

This area, with its bayside beauty and more than 350 years of history, inspired James Michener to write the epic novel Chesapeake. In Easton, the restored, art deco Avalon Theatre hosts nationally known performing artists, while crafters display their wares at nearby specialty shops. You can also tour a winery, get a taste of the dining scene or enjoy outdoor activities ranging from hiking and canoeing to championship golf.

St. Michaels, a former shipbuilding center now popular among pleasure boaters, features the Chesapeake Bay Maritime Museum with its working boatyard and restored 1879 lighthouse. A short drive away is Tilghman Island, which offers skipjack cruises and fine local cuisine. Head to Bellevue, where a historic ferry crosses the Tred Avon River to reach Oxford, another boating town with its own museum. Also in the area are the captivating colonial town of East New Market and the tiny fishing village of Secretary. Bike routes throughout the flat land have wide-open country views.

The Harriet Tubman Underground Railroad National Scenic Byway begins in south Cambridge, which has an active arts scene and a large maritime museum. Natural splendor is found at sites such as the Blackwater National Wildlife Refuge, which hosts the East Coast’s largest nesting population of bald eagles. 

Lower Eastern Shore section from Vienna to Crisfield

Including MD 313 & MD 413

From Vienna, known for its rich Nanticoke River and Chesapeake Bay legacy, this section of the byway has two travel options. One travels north to Federalsburg, where a scenic creek flows from the Idylwild Wildlife Management Area and winds through town. The other heads east toward the urban center of the region, Salisbury. History and culture mingle with a pedestrian-friendly shopping plaza, a museum of wildfowl art, minor-league baseball and a zoo.

In Whitehaven, a rural village below Salisbury, the historic Whitehaven Ferry runs on the Wicomico River. Then, in Princess Anne, the 200-year-old, neoclassical Teackle Mansion rests among 300 Federal-style and Victorian structures. West of town, the Deal Island Wildlife Management Area is one of the state’s finest places to view ducks and geese.

One of the southernmost spots in Maryland is Crisfield, famous for its local seafood, peaceful water trails and annual Hard Crab Derby. Cruises and ferries run from here to nearby Smith Island.

Image Credit:

Maryland Lore

Celebrated author James Michener wrote an outline for his novel Chesapeake in an Oxford tavern that won his heart with its succulent crab cakes.

Image Credit: erocrunfaster-instagram

Byways in this Region

Cape to Cape
Mason & Dixon

Byways Guide & Map

Maryland Scenic Byways Travel Guide and Map

Learn more with our FREE Maryland Scenic Byways Travel Guide & Map Start planning your road trip with our official guide and map.