Top Places For

Cycling Country Roads

Many of the Chesapeake’s most beautiful places are tucked down country roads, just waiting for you to discover them. And one of the best ways to explore these picturesque places is by bicycle.

On a bike, you can slow down, smell the fresh air, and savor the scenic beauty of the Chesapeake’s fields, marshes, and forests. Take off from a state park like Tuckahoe, Greenwell, or Trap Pond and spend a day exploring our region’s most scenic backroads. Most of these places are perfect for riders of all levels, whether you’re training for a race or simply enjoying a day outside with your friends.

From the flat, swampy lands of the Eastern Shore and Tidewater to the rolling hills of western Maryland and Virginia, you can explore nature and history on one of these cycling tours.

Get ready to hop on your bike and cruise the Chesapeake’s scenic byways at the top places for cycling country roads.

Note: Bicyling on country roads can be hazardous. While there tends to less traffic on country roads, typically there are only two lanes without a bike path and roads can have lots of turns, limiting visibility for drivers. A couple of suggestions: 1.  Always ride with traffic – on the right side. 2.  Use a mirror all the time.   3.  Never ride with ear buds listening to music or anything else - as hearing is a critical safety consideration. 

Antietam National Battlefield & Cemetery

Antietam National Battlefield & Cemetery

Antietam National Battlefield commemorates the American Civil War Battle of Antietam that occurred on September 17, 1862 and includes a visitor center, a national military cemetery and a field hospital museum.

Sharpsburg, MD

Fog Covered Blackwater National Wildlife Refuge

Blackwater National Wildlife Refuge

An Eastern Shore wildlife refuge attracting vast numbers of waterfowl to quintessential Bay tidal wetlands. While primarily a tidal marsh, the refuge also includes a mature pine forest.

Cambridge, MD

Blue Ridge Parkway scene

Blue Ridge Parkway

A Blue Ridge Parkway experience is unlike any other, a slow-paced and relaxing drive revealing stunning long-range vistas and close-up views of the rugged mountains and pastoral landscapes of the Appalachian Highlands.

Asheville, NC,

Tree Lined Road Through Catoctin Mountain Park

Catoctin Mountain Park

With 25 miles of trails winding through Catoctin Mountain Park, a variety of experiences are available ranging from easy to strenuous, many leading to outstanding scenic vistas.

Thurmont, MD

Cedarville State Forest

Cedarville State Forest

The Cedarville State Forest is more that 3,500 acres of protected lands encompassing the headwaters of the Zekiah Swamp, Maryland forests, and agricultural lands.

Brandywine, MD

Chesapeake Bay Maritime Museum

Chesapeake Bay Maritime Museum

Introducing visitors to the Bay story, and telling the Chesapeake's maritime history on the Eastern Shore. The museum houses examples of historic bay working boats, exhibits, guns, decoys, ship models and the 1879 Hooper Strait Lighthouse.

St. Michaels, MD

Sunset at Colonial National Historical Park

Colonial National Historical Park

Colonial National Historical Park is located in the Hampton Roads region of Virginia and includes Historic Jamestowne, Yorktown Battlefield, Colonial Parkway, and Cape Henry Memorial.

Jamestown, VA

Bridge at Cunningham Falls State Park

Cunningham Falls State Park

Cunningham Falls State Park is located in the picturesque Catoctin Mountains, opportunities including swimming, hiking, fishing and canoeing are available.

Thurmont, MD

Hikers at Elk Neck State Park

Elk Neck State Park

Elk Neck State Park boasts 2,188 acres of sandy beaches, marshlands, and heavily wooded bluffs within the peninsula formed by the North East River, Elk River, and the Chesapeake Bay.

North East, MD

Gambrill State Park

Gambrill State Park

Gambrill State Park is a beautiful mountain park, located on the ridge of the Catoctin Mountains in Frederick County. Its most popular feature is the 16 miles of trails for hiking, mountain biking, and horseback riding.

Frederick, MD

Sunset at Gettysburg

Gettysburg National Military Park

The Battle of Gettysburg was a turning point in the Civil War, the Union victory that ended General Robert E. Lee's second and most ambitious invasion of the North.

Gettysburg, PA

Greenwell State Park

Greenwell State Park

A recreational park along the beautiful Patuxent River that also provides special programs and facilities for the handicapped.

Hollywood, MD

Marsh at Merkle Wildlife Sanctuary

Merkle Wildlife Sanctuary

Merkle Wildlife Sanctuary encompasses almost 2,000 acrees adjacent to the Patuxent River. The habitat is managed primarily for geese, but many other wildlife can be seen here.

Upper Marlboro, MD



When visiting Monticello you can tour the mountaintop house that Jefferson designed and built for himself and his family, enjoy the beauty of its grounds, and explore the complexities of Jefferson's enduring global legacy.

Charlottesville, VA

Onancock Historic District and Town Wharf

Onancock Historic District and Town Wharf

Explored by Captain John Smith in 1607 and chartered in 1680, Onancock is one of King James' original 12 royal ports in Colonies. Today it remains a working port for watermen and waterborne commerce and recreational boaters.

Onancock, VA

Patuxent River Park Jug Bay Natural Area

Patuxent River Park Jug Bay Natural Area

Jug Bay Natural Area offers many activities including walking through wetlands, guided boat tours, hiking and horseback riding over eight miles of trails, boating, fishing, camping, hunting, and visiting a museum.

Upper Marlboro, MD

Visitor Center at Sailor's Creek Battlefield Historical State Park

Sailor’s Creek Battlefield State Park

Sailor's Creek Battlefield Historical State Park is a great place to stop for a picnic lunch because it's midway between Petersburg and Appomattox Court House.

Rice, VA

Water view of Smith Island Center

Smith Island Center

Small museum on Smith Island, home to many working watermen, tells the story of working and living on the Bay.

Ewell, MD

Scenic Overlook View at Sugarloaf Mountain

Sugarloaf Mountain

Sugarloaf Mountain has been designated a Registered Natural Landmark because of its geological interest and striking beauty.

Dickerson, MD

Trap Pond State Park

Trap Pond State Park

Nationally known for its scenic bald cypress stands and the James Branch Nature Preserve, Trap Pond State Park oversees 2,685 acres of land that offer recreational opportunities to the public.

Laurel, DE

Paddler at Tuckahoe State Park

Tuckahoe State Park

Tuckahoe State Park is a great place to get a feel for part of the Eastern Shore and the beginnings of the streams that eventually flow to the Bay. The park offers fishing, boating, hiking, biking, equestrian trails and more.

Queen Anne, MD

Underground Railroad Scenic Byway

Underground Railroad Scenic Byway

A drive along the 125 mile Underground Railroad Scenic Byway highlights the life of Harriet Tubman and many historic places connected with her in Chesapeake Bay country.

Cambridge, MD

July 10, 2017

Main image: A group of bicyclists along the Blue Ridge Parkway (Image courtesy: Brampton Cyclist / Flickr)
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