Bicycling Vacation at our Historic Eastern Shore Bed and Breakfast


eastern shore bed and breakfast's historic downtown

We have a saying around here: “If it’s early May, then it must be biker week.”  (Bicyclers, that is.)  Each spring and fall, we have the distinct pleasure of hosting two very fine bicycling vacation groups here at our historic eastern shore bed and breakfast.

Based in North Carolina, Carolina Tailwinds has been visiting with us for the past 5 years. Anne and Greg Fleming run a pretty tight ship (or should that be “bike”) and offer terrific cycling vacations throughout Maryland, Delaware, Virginia, New York  and, of course, the Carolinas where they’re from.

eastern shore bed and breakfast

They stay at our Chestertown b&b and bike all over Kent County; then they cycle off to other charming hamlets around the eastern shore: Lewes, Delaware and St. Michaels, Maryland among them. Good food and fine lodging are part of the package all the way through your trip.

eastern shore bed and breakfastThey get your bike ready for you, give you maps, feed and entertain you, and even let you ride in the van if you’re tired!

The Tailwinds’ groups always arrive on a Sunday, and often it’s just right after another cycling group leaves our Chestertown b&b:

eastern shore bed and breakfast

Bike Vermont obviously started their touring business in their home state of Vermont, but over the 36 years they’ve been in business, it has expanded to a few other states and into Europe. They arrive on Fridays, bike all weekend and leave on Sunday.  When they overlap with Tailwinds, it looks a bit like a cyclist convention is in town!  The same guides have led the Chesapeake Bay tour for the last few years and we’ve gotten to know both Bill and Meg well: not only for their love of cycling and customer service, but for their good humor as well…

And Bill just won’t rest until he’s sure everyone is happy, including Rita’s dog Sidney…

So wherever you live, if you are looking for an active travel adventure, please check out both of these wonderful groups, and tell them the folks from Brampton Inn sent you. Either way, it’s guaranteed fun!!

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