Maryland's Chesapeake Bay Bike Tour (trip)

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Maryland's Chesapeake Bay Bike Tour

  • Active & Adventure
Maryland bike tours , Inn to inn biking maryland , supported bike ride maryland , Chesapeake bay biking routes , eastern shore bike routes , East, Maryland, United States

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Period offered: April, October. The provider (view their profile) can provide you with specific departure dates, final prices, and other information.


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from $1,250* per person4 DaysApril, October
Boutique accommodations Exertion level: 4
Operator: Wilderness Voyageurs 12 people max
Imagine pedaling along the coast of the Chesapeake Bay, through the farmlands of the Eastern Shore of Maryland, around historic towns, relaxing on the coast, enjoying the ease of riding the flat coastal terrain....it is a trip to enjoy!

Meeting in Annapolis, Maryland, we will do a quick shuttle south to the western shore of the Chesapeake Bay.  Today we will ride along the Calvert Cliffs and end in Solomon, MD.   A boat ride across the Bay to Hoopers Island, rich with Eagles and other birds of prey.  Blackwater National Wildlife Refuge will host us for the afternoon.  Explore the history rich waterman’s communities of St. Michael's and Oxford.  Reflect on your days ride as you lounge in the front yard of the Inn, watching the birds play in the water.

You will ride along the bay, through large inland farms and woodlands, and visit 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 migrant peregrine falcon. The Refuge is unique in that it hosts the largest remaining natural population of Delmarva fox squirrels and is also host to the largest breeding population of bald eagles on the East Coast, north of Florida.

Locations visited/nearby

Maryland bike tours , Inn to inn biking maryland , supported bike ride maryland , Chesapeake bay biking routes , eastern shore bike routes , East, Maryland, United States

0 testimonials about this trip.

1 testimonial about the provider, Wilderness Voyageurs:

  • Reviewer: Ellen Goldman located in Phoenix , AZ USA
    "Hi Eric. We wanted to let you know about our experiences whilecycling from Pittsburgh to D.C. If someone had told us 6 months ago that we would be doing this, we would not have believed it. Although we both are physically active, neither of us had ridden bikes since we were much younger. But, our more experienced biker friend (Jay Rochlin) convinced us to start riding, and even provided one of us with a bike. So, after 3 months of training, we set off to Pittsburgh. This trip turned out to be the best vacation we have ever had. One of the major reasons that it was so great was Aaron. We couldn't have asked for a better guide, chef, driver, supporter. We all rate him "exceeds expectations" in all categories we could possibly consider! Not only was he extremely kind, knowledgeable about a multitude of things including bicycles, food, sights, interesting facts, etc, he was also always available when we needed him, and extended himself beyond expectations. And he always had some different snack or food for lunch every day to surprise us and keep us well-fed and energized. Our trip was so well organized and planned out, and yet we felt comfortable altering the schedule when we wanted or needed. The accommodations were wonderful- staying at a different B&B or Inn every night just added to the experience and every place was unique. We couldn't imagine doing the trip without the organization and support provided by all of you. In addition, the bikes we rented were not only new, but excellent for the terrain. It would have been much harder riding without the shocks! Of course, the other factor of the trip was the incredible scenery along the way. We don't even know how to describe how incredibly beautiful it all was. We especially loved the Great Allegheny Passage. To be able to ride for 300 miles on paths through amazingly beautiful country without cars was unbelievable and we can't imagine that any other place could be any better! We are all very proud of ourselves for completing the ride. We hope that Aaron enjoyed us as much as we enjoyed him. :)

    Please pass on our comments to Aaron and everyone else who helped make our trip memorable. We will definitely recommend you to all of our friends. And, hopefully return for a rafting trip next time!

    Thanks to all of you.

    Ellen G & Eddie K

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Itinerary

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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