Why Go: The Delmarva Peninsula (Delaware-Maryland-Virginia) is a bucolic, 170-mile-long peninsula that separates Chesapeake Bay from the Atlantic. A crazy quilt of fields, small towns, coves and sinuous tributary rivers, it’s the perfect place for a laid-back, low-speed ramble along the Eastern Shore’s low-country back roads.
Road Notes: If you start from historic 17th-century Easton, you can be in St. Michaels, seated on the waterfront patio at The Crab Claw in time for lunch — steamed blue crabs with Old Bay and a side of pickles and cheese — with a view. Then it’s on to Bellevue, where a ferry ride delivers you across the Tred Avon River to Oxford. From there, it’s am easy 13-mile pedal to Easton past cornfields and horse farms.
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Distance: 31.9 miles
Elevation Gain: 639 feet
Starts From: Easton, MD