Chesapeake Country Scenic Byway - Eastern Shore, Maryland

Chesapeake Country Scenic Byway - Chesapeake Bay Guide

State: Maryland
Length: 85.5 mi / 137.6 km
Time to Allow: 2.5 hours to drive, 2-3 days to visit the entire byway

Celebrate life on the Chesapeake Bay. Observe watermen bringing their bounty to shore, visit historic towns, and travel through scenic stretches of productive farmland. See the truly special landscape of the Mid-Atlantic Region and gain an appreciation for the working life of Maryland's Eastern Shore farmers, watermen, and merchants

A Day on the Bay of the Chesapeake Country Scenic Byway

Drive the Chesapeake Country Scenic Byway and experience small-town America at its best! The relaxed environment of the Delmarva Peninsula creates a contrast with the booming city life across the bay -- charming small towns, rich colonial history, spectacular wildlife refuges, manifold maritime recreation, and outstanding scenic views of the Chesapeake Bay and its tributaries. Experience the byway’s many remarkable facets as you explore captivating Chesapeake Bay.

Love history? Follow the footsteps of Captain John Smith at the Chesapeake Exploration Center, near Stevensville, the southern terminus of the byway. At the Exploration Center, you can pick up a map of the Captain John Smith Chesapeake National Historic Trail. Designated in 2006 by Congress, the trail follows John Smith’s voyages around the Chesapeake region and covers portions of the byway. Want to come even closer? Board the Schooner Sultana in Chestertown and take a John Smith Expedition aboard a replica of a 1768 British schooner for a taste of the area’s rich colonial history. If you prefer to stay on land, take the History on the Waterfront audio-guided tour of Chestertown's 18th-century waterfront district. Visit Georgetown and learn about legendary beauty Kitty Knight, whose strong will and bravery in defending an invalid neighbor stopped the British forces from burning a church and two brick houses. The byway is a treasure trove of finds for any history buff!

Are you a birder? Then grab your binoculars and head to some of the wildlife refuges along the byway. With easy access to five state parks and the Eastern Neck National Wildlife Refuge, you’ll have a thrilling birding and wildlife-viewing adventure! Visit Terrapin Nature Park, near Stevensville and see Great Blue Herons, ospreys, swans, and a variety of songbirds. Want more? Then visit Elk Neck State Park, where you can view seasonal birds like hawks, raptors, warblers, flycatchers, cuckoos and finches, Foster’s terns or year-round residents including Bald Eagles, Bluebirds, cardinals, goldfinches, and Meadow Larks. The byway is situated along the Atlantic Flyway and provides endless opportunities to catch a glimpse of a wide range of migratory waterfowl.

Love ships? Come experience the maritime culture of the Chesapeake Bay. See schooners, shallops, clippers, bug-eyes, dead-rises, and skipjacks. Canoe or kayak in shallow areas of the bay or its tributaries to obtain quiet and solitude, or take a larger boat and explore its deeper waters. The bay has over twenty launch ramps and thirty-some marinas. The traditions of working the waters can be seen from ports of call in Rock Hall and Kent Narrows. Try your hand at soft-crabbing, where you try and catch a blue crab after it abandons its shell, or fish for Alewife, Bluefish, or Perch, or the much sought-after Striped Bass (call it "rockfish" if you want to be mistaken for a local.) Come explore the picturesque rivers, creeks, and the bay that give the byway some of the finest fishing and water recreation opportunities in the U.S.

See the wonders of the Chesapeake from a bicycle. Want an easy ride? Try the Cliff City Crabber's Special which starts in Chestertown. Craving more? Take the challenging fifty-mile Rock Hall Ramble and explore the scenic vistas of Rock Hall. Whatever route you pick, you'll pedal past historic sites and quaint and fascinating shops. Stop in for a well-deserved lunch at one of the famous restaurants in the area, replenishing your energy with fresh-caught seafood cooked to perfection or some of the mouthwatering crab cakes Maryland is famous for.

As you travel among the towns along the Chesapeake Country Scenic Byway, revel in the early American history around you, spend your days playing among the waves in the Chesapeake Bay, and enjoy the rural mid-Atlantic culture. If you don't want to leave right away, the area's exquisitely restored bed and breakfasts allow you a chance to fully experience the wonders of the Chesapeake.

Chesapeake Country Byway Boating

Raise the sails, rev the motor, or pick up a paddle to discover boating bliss on Maryland's Chesapeake Country Scenic Byway. Celebrate boating in all its forms on the welcoming waters of this area's canals and rivers—and, of course, the Chesapeake Bay.

From Chesapeake City on the byway’s northern end, you can access the busy transportation waterway, the Chesapeake and Delaware (C&D) Canal. Although you can’t sail, paddle, or tow a water-skier, you can cruise amidst barges and other commercial boats as long as your boat is motorized. Don’t have a boat of your own? Then join a canal tour and learn about canal culture from the knowledgeable captain. You can also stop at the Canal Museum in Chesapeake City to learn about the canal’s early days, from its manual labor-intensive construction to steam-powered ships and pump houses.

In Chesapeake City each June, come by boat to the Canal Day Festival. Take advantage of the free shuttle-boat service that brings you right to the harbor and the onshore festivities. Check out crafts, enjoy food, and listen to music during this celebration of the historic waterway that still hosts plenty of commercial and recreational boating today.

Fourteen miles south of Chesapeake City is Georgetown, one of three sites on the Sassafras River where you can launch a canoe or kayak. Paddle through marshlands, beaches, farmlands, and bald eagle nesting sites, where larger boats can't go. If you make your way west toward Betterton Beach where the Sassafras River meets the Chesapeake Bay, you can moor your canoe or kayak at the pier, not far from the public restrooms and bathhouse. Here you can picnic under the pavilion, or just watch swimmers enjoy the sandy beach and cool waters.

From the many port cities along the Chester River, including Chestertown, which is 15 miles south of Georgetown, voyage out on the Chesapeake Bay aboard the meticulously reconstructed historic schooner, Sultana. Help with the rigging during a two to eight hour public sail, or explore the crew’s quarters below deck during an open house when the boat is docked at a port city along the byway.

At Sultana’s homeport of Chestertown, celebrate the end of the sailing season with Downrigging Weekend. Watch, board, and even sail on one of the dozens of sailing ships arriving at the Chestertown harbor in late October and early November each year for this event.

For a less conspicuous, but equally enjoyable boating experience on the Chester River, launch a canoe or kayak at several launch sites and public docks from Chestertown’s riverfront High Street Park to Boggles Wharf on Eastern Neck Island. Canoe past private preserved 18th century homes lining the banks near the city and work your way through peaceful farmlands to the Eastern Neck Wildlife Refuge.

Continue along the byway just past Queenstown and discover more boating waterways within the Chesapeake Bay Environmental Center. From here you can rent a kayak or canoe and glide through Marshy Creek, the Narrows, and Prospect Bay. Appreciate beautifully restored shorelines, natural marshlands, and abundant waterfowl, as you float on the tranquil waters of the self-guided trails in this area.

If that’s too quiet for you, head east of the Environmental Center to Kent Island in early August for the annual Thunder on the Narrows powerboat-racing event. Take your family to cheer on your favorite boat in each racing class, and grab something to eat from the on-site options when you’re hungry.

Get out and enjoy the abundant waters near Maryland’s Chesapeake Country Scenic Byway by sailing, kayaking, canoeing, cruising, or participating in a fun-filled waterfront celebration. Mark your calendar for the annual events and fill your summer days with exciting boating excursions on Chesapeake Bay and its tributaries.

Thumb Grant Golfing on Chesapeake Country Scenic Byway

A golf course on the southern end of Chesapeake Country Scenic Byway boasts an interesting glimpse into local history. Queenstown Harbor Golf Links, designed by local favorite Lindsay Bruce Ervin, is located on the first "thumb grant" in the state. In 1658, Lord Baltimore awarded English colonist Henry Coursey all that his thumb could cover on the map. This amounted to 1,200 acres, 700 of which provide one of the region's best golf experiences.


Golfing in Queenstown, MD
Public domain. Photo by John J. Rafferty of Annandale, VA



Today, golfers thank Coursey's thumb for covering prime property in Queenstown. The complex boasts two 18-hole courses, named The River and The Lakes. The River awards enthusiasts with a tough challenge where accuracy trumps power, while The Lakes provides an easier, natural golf experience among native wildlife.

Limitless Birding in Chesapeake Country

Fond of fowl? Bonkers for birds? A trip to Chesapeake Country is sure to leave any bird-lover in awe. The region is full of Wildlife Management Areas, parks and preserves, and other excellent ways to experience a byway that is for the birds.

The Chesapeake Country Scenic Byway encompasses much of the Atlantic Flyway, a main bird-migration route. The Eastern Neck National Wildlife Refuge is on the Flyway and offers glimpses of Canadian Geese, Snow Geese, swans, and ducks in flight. Hundreds of Osprey, shorebirds, and songbirds take up residence at the refuge. And with over one hundred Bald Eagles, the refuge boasts one of the largest eagle populations in the country. Come visit during the prime birding season from mid-October to mid-March for a chance to see birds migrating and raising their young.

A plethora of Wildlife Management Areas in the Chesapeake region will give you endless birding opportunities. Head over to Fishing Bay Wildlife Management Area for great birding. The largest wildlife management area in Maryland, this 21,000-acre area encompasses marshland and dry islands for ducks and geese. Eagles and Osprey enjoy dining on fish from the open waters. Mallards, teal, gadwall, pintails, and Canada Geese are among the other species that inhabit this area. Next, bring your binoculars to Sassafras River Natural Resource Management Area. Home to colorful songbirds like the Scarlet Tanager who dwell in the dense forests of oak, maple, and pine. The contrast of these birds against the deep green backdrop is astounding.

From waterfowl in migration and majestic eagles soaring above the trees, to chipper songbirds and graceful swans, Chesapeake Country is arguably the most spectacular birding location in the country.




Note: Highlighted byway routes shown on maps of All-American Roads and National Scenic Byways correspond to designations made by the U.S. Secretary of Transportation. State designations may differ.




Chesapeake Country Scenic Byway Information

Credit: U.S. Department of Transportation

Federal Highway Administration
Visit: http://www.byways.org/explore/byways/2261/