The mild weather and terrain make for an incredible cycling destination. Throw in wonderful lodging and quaint old town districts, you may want to move to the "Eastern Shore" after this trip. The landscape is dotted with working farms, centuries old churches and cemeteries.
Day 1: We embark on our adventure from the Tidewater Inn, Easton Maryland. Easton, recently named the 8th Best Small Town in America, is the county seat of Talbot County and formerly the capital of the colonial Eastern Shore. Settled in the 1680’s, Easton is overflowing with colonial and Victorian architecture that house countless antique, craft and boutique shops. Walking down main street, or any street in Easton, is stepping back over 300 years to a time when our shores were governed by royalty.
Day 2: After a few hours enjoying the town of Easton in the morning, you will set off biking by heading south to the quiet port town of Oxford. Explore the waterman’s town that James Michener used as the backdrop for his novel “Chesapeake” before enjoying some locally caught crab cakes and a private water front porch.
Day 3: We start the day with a shuttle to the Blackwater National Wildlife Preserve. Blackwater is a haven for several troubled species including the American Bald Eagle, the endangered Delmarva fox squirrel, and the Peregrine Falcon. This afternoon we travel to an 18th-century jewel on Maryland’s Eastern Shore, Chestertown. This town dates to 1706 when it served as a thriving Mid-Atlantic port and prosperous shipbuilding and trading center.
From its perch on the banks of the Chester River, the town today boasts a treasure trove of perfectly preserved 18th and 19th century homes that once belonged to Chestertown’s wealthy merchants. “Chestertown is a treasure hidden in plain sight,” said Richard Moe, president of the National Trust for Historic Preservation.
Day 4: Your final day will have you riding out of your lodging, across the Chester River and through the verdant and rich tapestry of agricultural landscape that is Queen Anne’s County. Your ride will terminate back in Easton, Maryland where we will bid our farewells.
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USA Maryland Outdoor: Land Rambler Bicycle Touring Sightseeing
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