Here Are the Top Festivals and Events to Attend in Chestertown, MD!

No matter what time of year you visit historic Chestertown, you’ll be greeted with plenty of lively events, festivals, and local happenings. Fans of the winter season love the area’s lively hunting scene, while spring and summer lovers delight in the many music festivals held here in warmer weather. Finally, fans of the fall can’t get enough of our cool-weather jazz events. It doesn’t matter if you’re athletic, easygoing, young, or old—there’s a special celebration waiting for you here! Below, we’ve listed the top festivals and events to attend in Chestertown, MD. If you’d like even more local insight, be sure to claim your free Eastern Shore Travel Guide!

The Top Festivals and Events to Attend in Chestertown, MD

Winter

Holiday High Tea and Christmas Readings at Brampton Inn

Every December, one of our most loyal guests, Stokes Tomlin, graces us with his dramatic oratory skills. Dressed in historical period garb, Tomlin reads holiday-inspired literature such as Truman Capote’s “A Christmas Story.” Guests gather in the parlor, we light the fire, and the fun begins! The readings normally last about 30 minutes. Then, everyone gathers in the dining room, we pour some wine, and some delicious food is served. That’s the Christmas Reading and Holiday High Tea in a nutshell!

Oyster Festivals

You may already know that winter is prime oyster roast season! The Eastern Shore of Maryland is no exception! Every January, Brampton Inn hosts its own private oyster “festival,” (more of a festive dinner) and it’s one you shouldn’t miss. At this dinner, oysters from the Chester River are served four different ways with a winter salad and sparkling wine. The best part about this “festival?” It’s indoors and next to a glowing, real-wood fire!

Spring

Taste of Chestertown

If there’s one event in Chestertown, MD, you need to attend this spring, it’s Taste of Chestertown (also known as “Taste of the Town”)! During this iconic Maryland festival, you’ll taste your way through a tantalizing variety of locally prepared dishes and wine samples. If a cornucopia of crab soup, beef brisket, oysters, gnocchi, and lemon pie sounds like your kind of meal, get your tickets for Taste of Chestertown! Proceeds benefit the Samaritan Group of Kent County, so you can feel good about your purchase.

Chestertown Tea Party Festival

One of the best festivals on the Eastern Shore takes place on Memorial Day Weekend right here in Chestertown! The Chestertown Tea Party Festival is a celebration of the town’s Revolutionary War history. Of course, you don’t have to be a history buff to join in the fun! This festival has a street party atmosphere—there’s food, drink, live music, vendors, and even a crazy raft race! Be sure to mark your calendar for this one.

Summer

Kent County Fair

Summer is a perfect time to get out, enjoy the great outdoors, and make some memories with your loved ones! The Kent County Fair is our area’s take on this beautiful time of year. This 4H fair is fun for the whole family and benefits local youth agricultural education. Expect a horse show, dog agility contest, a petting zoo, rides, and plenty of vendors!

Pirates and Wenches Fantasy Weekend

Ever dreamed of sailing the seven seas and shivering timbers? You’re in luck! Held just a short drive away from Brampton Inn (in Rock Hall, MD), the Pirates and Wenches Fantasy Weekend offers immersive fun for everyone. Buccaneers and land-lubbers will rejoice in this themed, town-wide party every August.

Fall

Harry Potter Festival in Chestertown, MD

Starting to notice a theme? Chestertown is a hub for lovers of the fantasy genre! If you long to play a game of Quidditch and surround yourself with people who love The Boy Who Lived as much as you do, this festival is for you! The Harry Potter Festival in Chestertown, MD, takes place every October in historic downtown Chestertown.

Sultana Downrigging Weekend

Last but certainly not least, attending the Sultana Downrigging Weekend is an amazing way to kick off the fall season! This “tall ship and wooden boat festival” is so much more than meets the eye. Yes, hobbyists will love experiencing these stunning vessels in person, but this event also features live music, Dock Dogs competitions, and fireworks. You won’t want to miss this celebration of the Chesapeake Bay area’s rich nautical culture!

Brampton Inn Offers Some of the Best Chestertown, MD, Events!Olivia's Cottage at Brampton Inn; near the top festivals and events to attend in Chestertown, MD

After having an unforgettable experience at one (or more) of these Chestertown, MD, events, you’ll need a comfortable and beautiful place to stay. Here at Brampton Inn, our guests are treated like family! Our bright, airy, and spacious accommodations offer a respite from the hustle and bustle. Here, you can sit back, relax, and “porch surf” with us (trust us…it’s a thing)! In the morning, you’ll love waking up to fresh, country air and our homemade, gourmet breakfast. During special times of the year, Brampton Inn also hosts a variety of festive events. Isn’t it time you came to experience them for yourself?

Ready to experience an incredible getaway to the Eastern Shore of Maryland? Check our availability today! We’re looking forward to your visit.