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Maryland Chesapeake Weekend Bike Tour
Trip Overview
Celebrate spring or savor the fall with a weekend of easy coastal riding on quiet roads. Visit a fascinating variety of historic Tidewater Maryland villages on your bike tour and indulge in local cuisine including clams, oysters, and the best crab cakes in the world. Our tour is based in the quaint waterfront town of Saint Michaels, whose historic streets are lined with Colonial-era houses and shops, evidence of its former eminence as a prosperous shipping and trading center.
While in Saint Michaels, you might take the opportunity to explore the highly regarded Chesapeake Bay Maritime Museum, where you can learn about the history of the bay and its traditions in boat building, commercial fishing, yachting and navigation. There are 23 buildings on 18 acres with interactive exhibits, the popular Hooper Straight Lighthouses, and several historic vessels docked at the waterfront boat yard.
Finally, the biking on this tour is perfectly designed for an early springtime or fall outing. Easy terrain, quiet tree-lined back roads, and beautiful vistas along the bay make for a wonderful weekend experience.
Itinerary
From start to finish, check out the route.
We begin our tour in the quaint waterfront village of Saint Michaels. Saint Michaels is situated on a picturesque peninsula between Tilghman Island and Easton and is well known for its interesting mix of history, shops, and small town charm.
Today’s ride features spectacular cycling on what is considered one of the premier biking routes on the East Coast. We ride a bike path through Easton and wend our way along back roads to Oxford, a charming, tree-lined village on the banks of the Tred Avon River that has been well-known for its boat building and maritime activities since the early settlers first arrived here. We recommend a great place for a bayside lunch, and our exploration of Oxford often ends with a visit to the Scottish Highland Creamery for a scoop of Victor Barlow’s homemade ice cream. After lunch Captain Tom Bixler welcomes us aboard the small Oxford-Bellevue Ferry. Founded in 1683, this privately owned ferry is believed to be the oldest in the country. After our crossing we ride pretty back roads through Royal Oak and Bellevue arriving back in Saint Michaels in time for a visit to the Chesapeake Bay Maritime Museum.
Our Sunday riding takes us north passing elegant manor houses before crossing the Miles River drawbridge. After passing the “Gothic” ruins of the St. John’s Protestant Episcopal Church (built in 1839), we pass through Unionville and by the historic Unionville cemetery where many soldiers from the Black Unionville Regiment are buried. We then ride the rural roads to the grounds of the “Little Red School House”, a still intact original one-room school built in the late 1800s and which now serves as a museum. From here we loop down along Goldsborough Road and Glebe Road and through Royal Oak back to the St. Michaels inn.
Map
Dates & Pricing
Prices are per person based on double occupancy (2 people in one room). Single supplement for private room is listed at the top of this page. A deposit of $750 holds your reservation for most tours. For tours less than 6 days, the deposit is $500.
What’s Included
Tour includes 2 nights of lodging; 2 breakfasts and 2 dinners; all taxes and gratuities at the hotels; free use of bicycle; experienced leaders; full van support; and detailed directions. We have additional optional miles for energetic riders on most tour days. Airfare is not included.
Dates & Pricing
Prices are per person based on double occupancy (2 people in one room). Single supplement for private room is listed at the top of this page. A deposit of $750 holds your reservation for most tours. For tours less than 6 days, the deposit is $500.
What’s Included
Tour includes 2 nights of lodging; 2 breakfasts and 2 dinners; all taxes and gratuities at the hotels; free use of bicycle; experienced leaders; full van support; and detailed directions. We have additional optional miles for energetic riders on most tour days. Airfare is not included.
Inns
Where you stay along the way.
Named one of the Top Ten Best Small Coastal Towns by USA Today, St. Michaels, Maryland is a charming place to spend some time, whether you're on a family vacation or a romantic getaway. St. Michaels Inn is located minutes from exciting attractions, from boating on the Bay to shopping in historic downtown. Learn about our storied past with a visit to the St. Michaels Museum and the Chesapeake Bay Maritime Museum. Walking tours are also available. St. Michaels is centrally located between Ocean City and Washington, DC, and just 12 miles from Tilghman Island.
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