Celebrating Memorial Day in Chestertown, MD

Small American Flags

The end of May signifies many things: the unofficial start of summer, excitement about imminent graduations, beach traffic, permission to wear white pants. (That’s not really still a thing, is it??) And of course, the end of May brings Memorial Day, a federal holiday meant to set aside time to reflect upon and honor those…

Come on down for the Taste of the Town!

Technically, it’s the taste of the Town and County, but that doesn’t make for a snappy headline or a catchy title, does it?? Yes, it’s time for the biggest foodie event of the year, and in 2017 it has reached a milestone: the 10th annual Taste of the Town. Sunday May 7, from noon to…

The Way We Worked: Traveling Smithsonian Exhibit Comes to Chestertown

While the Smithsonian Institution museums are only about 1.5 hours from Chestertown, that’s not exactly right around the corner.  A visit takes a bit of planning, and is usually an all day event. But what if you could visit a Smithsonian exhibit right in your own town? If that sounds good to you, then read…

Washington College & Washington’s Birthday

It’s no secret that Chestertown is steeped in history.  So is the entire Eastern Shore of Maryland. In fact, that’s one of the things that  many folks visit us for:  the chance to stay in a pre-civil war building; to tour 19th century homes that have been painstakingly restored; or to visit museums that depict the local history.…

Art Classes and Self Restoration: January in Chestertown

If you ever wanted to try painting with watercolors or throwing clay on a wheel, listen up: RiverArts Chestertown has some short term classes available this January and wouldn’t that be a great reason to come and visit the Brampton?  Treat yourself to a luxurious stay and express yourself with color and clay.  Oooh…look at…

Downrigging Weekend is Almost Here!

One of the biggest weekends of the year here in Chestertown is coming up soon:   “Down-rigging”, denoting the end of the sailing season, has over the past 15 years grown to be a weekend long festival filled with tall ships, music, food, fireworks, lectures, races, films, classic cars and wooden boats. And fun!  Always…

Getting ready for Fall Festival Season!

    Summer lasts roughly 14 weeks:  June 20 to September 21.  So why is it that when August rolls around, and it’s quite literally the middle of the summer, everyone starts acting like summer is over and it’s all about back to school and Halloween decorations??  Slow it down, people.   Life is short,…

HOT Summer Events Coming to Chestertown

Young kissing couple under big tree with swing at sunset

July is a HOT month. The temperatures rise and so do the choices of things to do in Chestertown! Our summer guests always look forward to the best of the best summer events that take place in Chestertown near our Maryland bed and breakfast this time of year. Music in the Park Concert Series The…