2 Historic Tours in Kent County, Maryland

Ahh, January:   quiet times after the flurry of year-end activity.  There is something comforting about the beginning of a new year.  Everything seems a little hushed.  It’s a good time for contemplation, and imagining what you want for your future.  It can also be a good time for reflecting on the past, and this area just happens to be steeped in history…

Quaint little Chestertown, MD has so much to offer to history lovers in general and African American history buffs in particular. The southern Eastern Shore is home to the Harriet Tubman Underground Railroad Byway, a self guided driving tour  featuring sites where Ms. Tubman lived, labored, and helped others gain their freedom.  At 125 miles, it’s quite extensive; check it out here.

Chestertown itself was the destination of Freedom Riders in the early 1960’s protesting segregation and marching for voting rights.  A fascinating history of the town’s racial divide, it can be walked in a day, as seen here.  Museums are great (we have our share of those too), but these self guided tours allow us  to literally “follow in the footsteps” of our forebears.   And it doesn’t hurt that driving around the Eastern Shore will guarantee some beautiful vistas.

Take in some of our nation’s rich history and stay with us at our cozy Maryland bed and breakfast. We’ll help you make the most of these special outings.

Toasting glasses of red wine in front of fireplace



Chestertown is the perfect location for a memorable staycation! Stay any 3 consecutive nights and receive 50% off your third night.

*Valid thru March 3, 2022 on new reservations only. Not valid with other special offers or third-party booking sites.