Downrigging Weekend and Boat Festival

For the third week in a row, we have a great weekend event to tell you about.  We are approaching the 13th annual Downrigging Weekend: Sultana Projects Tall Ship and Wooden Boat Festival.  This is one of the biggest weekends of the year for Chestertown with many  different activities going on including a concert at…

Maryland Kayaking :: Paddling In and Around Chestertown

As I write this, it’s a little damp and drizzly outside, but I just know that warm, beautiful springtime weather is right around the corner. A fun thing to do when the sun is out is to get on the water. Obviously, the Eastern Shore is famous for the Chesapeake Bay and the many rivers,…

Top 6 Eastern Shore Restaurants to Ring in the New Year!

  One of the nice things about living in a small town like Chestertown is being able to go out to a really nice dinner at a restaurant without having to call and reserve weeks in advance. For about 360 days of the year, that is. Memorial Day weekend, Graduation weekend and of course, New…

Post Sandy Update for our Maryland Bed and Breakfast

First, a big thank you to all of our friends and family for your concern and well wishes for our Chestertown Bed and Breakfast. We were so very lucky to have had no damage from the monster storm of Hurricane Sandy. Second, our heartfelt sympathy goes out to all of those suffering from the aftermath…

Chestertown MD is Crazy for “Crazy Days” – the Best Sidewalk Sale!

The temperature isn’t the only thing that’s hot at the end of July in Chestertown MD:  it’s the prices at Crazy Days:  the best sidewalk sale ever, held in the historic district of town on July 26-28, 2012.  The merchants set up outside their shops, and prices are slashed to move inventory and make room for…

On the Eastern Shore: Top 5 Places to Watch the Sunset

We are very lucky here on the Eastern Shore to have some of the best sunsets around. As there’s nothing more romantic than watching a sunset together (except maybe watching the sunrise, but that’s a different story). These are, in no particular order, the 5 top places we can think of to say adieu to…

Top 5 Entertainment Venues in and around Chestertown, MD

See a play. Watch a movie. Hear the chorale. View an old silent film. Dance to a swing band. Go to an open-mic night. All answers to the most frequently asked question: “If I come to Brampton Bed and Breakfast Inn, what is there to do?” Here are the Top 5 Entertainment Venues in Chestertown, MD: 1. The Garfield…