Chesapeake Country All-American Road

Known as the "Gateway to the World" the canal is listed on the National Register of Historic Places and a National Civil Engineering Landmark. Chesapeake City offers historic inns, restaurants, boat rides, a recreational trail and annual events.

The Riverside town of Chestertown, with its vast collection of historic sites, provides evidence and expression of early American life and the many ways our forefathers sought freedom. Chestertown includes the GAR Hall, Schooner Sultana, boat rides, restaurants, inns and shops.

A feature of international significance on the Atlantic Flyway, the 2,285 acre island refuge is a major feeding and resting place for migratory and wintering waterfowl. The refuge offers trails, a visitor center, public landing, scenic views and opportunities for birding and fishing.

Founded in 1682 and listed on the National Register of Historic Places, Old Wye Mill is one of the oldest continuously operating water-powered grist mills in the United States and is an exceptional representation of American ingenuity exemplifying early colonial life and farming culture on the Delmarva Peninsula. The mill is located in a park and includes a store where customers can buy local grains.

The Museum of Rural Life shares the Chesapeake Country story through exhibits that depict hundreds of years of rural and agricultural life on Maryland’s once isolated Eastern Shore.

The Chesapeake Bay Maritime Museum's 18-acre waterfront campus sits on Navy Point, overlooking the Miles River in the historic waterfront town of St. Michaels. The museum includes hands-on exhibits that provide an overview of Chesapeake Bay culture, history and nature, and the interdependence of humans with the Bay. Boat tours, a lighthouse, museum store, shipbuilding, and programs and lectures are available on site.

Chesapeake maritime culture is still evident today at Long Wharf, a working waterfront where Watermen and Waterwomen embark to dredge for oysters and catch crabs in much the same manner as their predecessors. Sailing tours, a replica lighthouse and public dock are available at the wharf.

Surrounded by wildlife in the heart of the Atlantic Flyway, the Ward Museum of Wildfowl Art features the world’s largest and finest public collection of decorative and antique decoys. The museum includes waterfowl carvings, a museum store and interactive puppet theater.

The Delmarva Discovery Museum on the Pocomoke River serves as a source of learning and discovery through the preservation and interpretation of its cultural and natural heritage. The museum includes exhibits with river otters, a children's play room and a museum store and offers field trips.

A true island community twelve miles west in the heart of the Chesapeake Bay, Smith Island is Maryland’s sole inhabited island, accessible only by a 45-minute boat ride and is a paddlers', bikers' and birders' paradise. On the island you will find restaurants, inns, and the famous Smith Island Cake.

Scenic overlook

The Chesapeake Heritage and Visitors Center, Ferry Point Park, The Cross Island Trail and the Cross County Connector Trail, and the Maryland Watermen's Monument all have signs to guide you. The Waterman's Boat Basin at Heritage Harbor is also an important feature of the area. It is home to many of the work boats and vessels run by the Queen Anne's County Watermen and the Black Captains of the Chesepeake. The Kent Narrows Development Foundation keeps an inventory of all heritage markets and heritage sites in the region. It publishes itineraries and the Watermen's Way Heritage Trail maps and brochures. The Harris Seafood shucking house is also here.

Beginning in 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.

Across the Sassafras 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.

Veer southwest 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 area that extends from Chestertown through Centreville and into Queenstown is famous for its large number of fine antiques shops.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. From Queenstown, make your way to Kent Island, featuring a number of options for dining and lodging.

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." 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 theMUSEUM 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 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.A sidetrack to the charming town of Denton leads to the Choptank River waterfront and theMUSEUM 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 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.

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.