Chesapeake Country

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

Once home to Chestertown's market house and armory, Fountain Park is now the town's welcoming center and a charming picnic spot.

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
11 Park St.
Earleville, MD 21919

Mount Harmon Plantation
600 Mount Harmon Rd
Earleville, MD 21919

Kitty Knight
14028 Augustine Herman Hwy
Georgetown, MD 21930

Kent Museum
13689 Turners Creek Rd
Kennedyville, MD 21645

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

Sultana Education Foundation
100 Cannon St.
Chestertown, MD 21620

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

Cross Island Trail
191 Log Canoe Cir
Stevensville, MD 21666

The Old Wye Grist Mill and Museum
900 Wye Mills Rd
Wye Mills, MD 21679

Museum of Rural Life
16 N. 2nd St
Denton, MD 21629

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-Bellevue Ferry
101 East Strand (end of MD Rt 333)
Oxford, MD 21654

Oxford Museum
101 S. Morris St
Oxford, MD 21654

Skipjack Nathan of Dorchester
100 High St
Cambridge, MD 21613

Choptank River Lighthouse
100 High St
Cambridge, MD 21613

Richardson Maritime Museum
401 High St
Cambridge, MD 21613

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

Pemberton Historical Park
5561 Plantation Ln
Salisbury, MD 21801

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

Teackle Mansion
11736 Mansion St
Princess Anne, MD 21853

Delmarva Discovery Museum
2 Market St
Pocomoke City, MD 21851

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

Smith Island
Smith Island
Smith Island, MD 21824

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. Walk or bike along the Ben Cardin C&D Canal Trail, to experience scenic views and the natural history of the area.

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 and National Historic Landmark, which 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. Get out on the water on the Captain John Smith National Historic Trail with a paddling or sailing tour led by the Sultana Education Foundation.

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 the Chesapeake Bay 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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Chesapeake Country

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

Enjoy an unforgettable getaway with something for everyone at the Hyatt Regency Chesapeake Bay Golf Resort, Spa & Marina in Cambridge.

Mid-Shore section from Wye Mills to Vienna

Including US 50, MD 322, MD 33, MD 333, MD 341 & MD 192

Head East on US 50 to Wye Mills and tour the Old Wye Grist Mill, to witness the oldest continuously working water-powered grist mill in the country. During the American Revolution, the Wye Grist Mill shipped barrels of flour via the Chesapeake Bay to the Continental Army, commanded by General George Washington. Historians dubbed the Eastern Shore the “Breadbasket of the Revolution."

A sidetrack to the charming town of Denton leads to the Choptank River waterfront and the Museum of Rural Life. Exhibits of four historic dwellings inside the museum provide a rare glimpse into the lifestyles of residents who, for 300 years, solely depended upon agriculture to earn a living.

Back on the main route, travel to Easton and beyond to the Tilghman Island peninsula.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. Just down the road 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. Bike routes throughout the flat land, such as the Oxford - St Michaels Bike Trail, have wide-open country views. Also in the area are the captivating colonial town of East New Market and the tiny fishing village of Secretary.

Cross the wide Choptank River and enter the city of Cambridge. On the waterfront at Long Wharf, the Choptank River Lighthouse creates an idyllic scene that belies the busy port that once existed here. Experience the scenic view aboard the Skipjack Nathan.  In its historic downtown, Cambridge’s active arts scene and a large maritime museum add to the cultural fabric of the city. Learn about Harriet Tubman's daring rescue missions at the Harriet Tubman Underground Railroad National Scenic Byway. 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.

Chesapeake Country

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

Paddle on the world-class water trails at Daugherty Creek and other waterways that weave through Janes Island State Park in Crisfield.

Lower Eastern Shore section from Vienna to Crisfield

Including MD 50, MD 54, MD 349, MD 352, US 13, & 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 here with a pedestrian-friendly shopping plaza, a zoo, minor-league baseball, and the Ward Museum of Wildfowl Art, featuring the world’s largest and finest collection of decorative and antique decoys. Nearby is the Pemberton Historical Park, which was once home to a thriving 18th-century plantation along the Wicomico River. Tour Pemberton Hall, furnished to reflect the pre-Revolutionary period, and explore trails to view marshlands, waterfowl, cypress trees and historic sites. 

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, as well as skipjacks, an historic sailing vessel used for dredging oysters.

Continue to Pocomoke City and the Delmarva Discovery Museum to explore how people’s lives have been shaped by the water and land. Get up-close with Diamondback Terrapins, Horseshoe Crabs, North American River Otters and more through hands-on exhibits about the Chesapeake’s habitats.

Follow the byway to one of the southernmost spots in Maryland - Crisfield - famous for its local seafood, peaceful water trails and annual Hard Crab Derby. Kayak or canoe among towering loblolly pine forests and tidal marshes with sandy beaches at Janes Island State Park  - a nature lover’s paradise.

Cruises and ferries run from Crisfield to nearby Smith Island Maryland’s only inhabited island accessible only by boat. Here visitors can see the Chesapeake watermen’s life in action at its docks, villages and at the Smith Island Crabmeat Coop. Don’t miss having a piece of Smith Island Cake, Maryland’s official state dessert.

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.

Equal parts celebration and foodie feast, there's nothing quite so quintessentially Chesapeake as good, old-fashioned Maryland steamed crabs.

Image Credit: erocrunfaster-instagram

Byways in this Region

Cape to Cape
Harriet Tubman Underground Railroad

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.