HOT Summer Events Coming to Chestertown

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 Music in the Park concert series is in full swing. Enjoy FREE outdoor concerts every other Saturday all summer long. We spend so much time in air-conditioned spaces and it’s easy to forget how pleasant it can be outside on a summer evening, especially when you’re sitting in a lawn chair, the sun is down, there’s a river breeze, and the music is free… ahhhhh…. summertime! Every other Saturday evening beginning June 11, 2016, from 7-8:30 pm you can sit outside and enjoy the best in local & regional music – including big band, bluegrass, folk, jazz, rock, and more! Don’t forget to bring a char! Saturdays – June 11, 15, July 2, 16, 30, Aug 13, 27.


Crazy Days

Yes, it can be a crazy hot month. Maybe that’s why we have Crazy Days at the end of every July. This Annual Sidewalk Sale is the absolute best time to shop in Chestertown. Remember our favorite store Twigs and Teacups? Here’s your chance to stock up on gifts and goodies for the whole year! Every store in town has its wares out on the sidewalks with slashed prices to make room for new merchandise. Books, clothes, jewelry, house wares, gift items, even the galleries participate. There’s also street food and a festival atmosphere in the air. Four days of bargain hunting starts July 28, 29, 30, & 31. Do not miss it!

Blue Crab Chesapeake Charters’ Sailboat Ride

For many years, we have been recommending a ride on Blue Crab Chesapeake Charters’ beautiful sailboat all season long. But for a really special treat, try them out on July 3rd. Yes, the 3rd of July is a big deal in Rock Hall, MD! Think of it as a preview of the fireworks on the 4th… but don’t tell that to anyone in Rock Hall. 🙂


Independence Day Extravaganza Cruise

The special Independence Day Extravaganza Cruise is a hour ride on the bay with hors d’oeuvres and the best seat you could imagine for fireworks. We’d love for the Blue Crab Charters to have a boat full of Brampton Inn guests. They only take up to 6 people out at a time. This is a fabulous way to enjoy the fireworks in Rock Hall, from on the bay itself!

We can’t wait to host you on your amazing summer retreat in Chestertown. Check our availability now and hurry because we fill up fast this time of year!

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.