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…

The Ultimate Music Experience in Maryland

Photo of a Violin

Are you and your loved one planning a romantic getaway in Maryland this summer? Or maybe you and your family are getting away for a special family vacation together. No matter who you’ll be traveling with, consider staying with us in mid-June so you can catch the National Music Festival. On Maryland’s Eastern Shore in…

A Chestertown Learning Vacation: Workshop with a Local Artist

A Unique Maryland Getaway As we’ve mentioned before, Chestertown is home to quite a few artists and artisans who are lucky to be able to make a living with their craft:  a lifestyle that many would like to emulate, but few are able to realize. Taking a year off to apprentice under a master is…

Surround your Valentine with Orchids at Longwood Gardens!

Roses may be the traditionally given flower for Valentine’s Day,  but not everyone always wants to be traditional.  Roses are lovely of course, but what if instead of flowers that will be gone in a few days anyway, you wanted to give the gift of an experience that you can share… and one that just…