Bike Trails on Maryland's Eastern Shore

Active & Adventurous - Outdoors

Scenic bike riding made easy


Talbot County, Maryland, on the peninsula of the Eastern Shore between the Atlantic Ocean on the east and the Chesapeake Bay on the west, has made scenic bike riding simple for both the casual and the serious biker, with tours that please bird watchers, too. The flat terrain is naturally easy. The dedicated trails and the purposefully wide roadway shoulders were designed to make biking safe. A sturdy and easy-to-follow bicycle map, “Bike Talbot County,” provides directions for six memorable bicycle touring trails—five of which are circuit trails—and contact information for rentals. The town of Easton, where four of the six Talbot County trails converge at the rails-to-trails lot, offers a shorter route for the more leisurely biker. One of the trails is even recognized as one of the top 25 cycling routes in the United States.

School Days 

Easton_Rails_to_Trails“Bike Talbot County” trail #1 is 28.3 miles and begins in Easton at the Rails to Trails parking lot, near the restored rail station. The route highlights county historical sites, including the Little Red Schoolhouse and Unionville’s historic cemetery, with the graves of soldiers from Black regiments that fought in the Civil War. The highlight of the trail for nature lovers is the Audubon Environmental Center at Pickering Creek, where blinds and observation platforms offer the opportunity to spot egrets, bald eagles, wood ducks, and herons. In season, migrating shorebirds are common. Rare birds have been seen here as well: Wilson’s phalarope, ruff, and northern shrike. 

Joust Maryland

Named for Maryland’s state sport, trail #2 is 26.7 miles and starts at Wye Oak State Park. The aptly named trail passes the site of the Maryland Jousting Association’s annual horse show and jousting tournament, at historic St. John’s Church. The trail also passes Wye Landing, typical of the steamboat docks that used to be an essential part of commerce on the Eastern Shore, the Wye Grist Mill, Old Wye Church, and the Old Wye Oak tree, the former state record tree.

Talbot Farmland

This 27.6-mile eastern loop, beginning in Easton, provides a peek at Talbot County’s farming industry, which accounts for 60 percent of land use, mostly in wheat, corn, and soybeans. Three side trails provide views of the Choptank River and a chance to rest beside a Chesapeake Bay tributary. Birders can enjoy this route for the glimpses of indigo buntings and blue grosbeaks as well as the prothonotary and yellow-throated warblers that have been seen near the bridge at King’s Creek.

Chesapeake Views

Although this is not a loop trail, the beautiful views of the Chesapeake Bay along this 38.2-mile trail will make a joy of driving the roads twice. Tilghman Island is a reminder of the importance of the water for much of the county’s history: watermen made their living off of oysters and other seafood, and water recreation provided pleasure and income. However, even on this peninsula, the agricultural industry is evident. Since the Chesapeake Views Trail is not a circuit trail, it would be an easy trail to tailor and trim, with three easy alternative parking spots along the way.

Oxford/St. Michaels

Talbot_County_town_300This 29.6-mile Talbot County Trail has been called one of the top bike trails in the Mid-Atlantic. It begins at the Chesapeake Bay Maritime Museum in the historic town of St. Michaels and makes its way through other quaint communities like Oxford and Royal Oak, with plenty of beautiful water views. The circuit trail includes a ride on the Oxford Bellevue Ferry, which is closed December through February. After the ride, bikers will find ample opportunities for unique shopping and dining and can learn about the area’s maritime history at the Maritime Museum, a variety of exhibits in 35 buildings on 18 waterfront acres.

Cemetery Quest

The 28.1-mile Quest provides a challenge, should you choose to take it: find all of the cemeteries on the map, some prominent from their proximity to a church, some small and easy to miss, with ancient tombstones or spreading periwinkle. The trail also provides a challenge to birders. The trail guide suggests two side trips for birdwatching into mature wetland forests around old millpond sites, where early spring migrant songbirds stop for rest and refreshments. However, the suggested locations aren’t obvious from the guide’s maps, so GPS or more detailed hard copy navigation would be helpful.

Talbot County Apres Ride

Bartlett_Pear_Inn_300After the bike ride, there’s no need to leave Talbot County’s visitor-friendly towns. Try dining at one of the county’s many quality independent, locally owned restaurants, several with culinary masters at the helm. Twelve local restaurants earned listings in the 2011 edition of the Zagat dining guide, including Bartlett Pear Inn, Mason’s, the BBQ Joint, and Scossa in Easton, and the Robert Morris Inn in Oxford. In Easton, find a morning boost or afternoon pick-me-up at Easton’s Coffee Cat’s beverages and food; a good beer selection and bar food at Washington Street Pub’s 50-foot-long bar, across from the Talbot County Courthouse in Easton; or decadent chocolates at Mason’s.

For entertainment in Easton, visit Academy Art Museum and the many private galleries; settle in to performances and independent films at Avalon Theatre; or enjoy live music at Coffee Cat’s alter ego, Night Cat. Get a deeper look into Talbot County history at the Historical Society of Talbot County in Easton or the Chesapeake Bay Maritime Museum or St. Michaels Museum in St. Michaels.  

Refresh from the day at any of the county’s stellar accommodations, including The Inn at Perry Cabin, Tilghman Island Inn, Tidewater Inn, and the Inn at 202 Dover, one of American Historic Inns’ “Most Romantic Inns in America.”

To get a bicycle trail map and to learn more about Talbot County, contact the Talbot County Office of Tourism at 410-770-8000 or The map can be downloaded as well.


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