What Are the Best Events on the Eastern Shore of Maryland?
Beautiful scenery, charming mom-and-pop shops, and a vibrant coastal culture are just some of the reasons why the Eastern Shore of Maryland is the perfect year-round destination. You certainly won’t run out of things to do here, either. Between historic monuments, a thriving arts community, premier shopping, and delicious food, there’s something for everyone here. We’ve listed some of the best events on the Eastern Shore of Maryland! While planning a trip around these exciting celebrations, be sure to access our free Travel Guide to the Eastern Shore of Maryland! It’s full of our best suggestions for making the most of your trip.
Don’t Miss These Annual Events on the Eastern Shore of Maryland
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), 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.
Cars on High
Every 3rd Thursday admire classic, exotic, antique and customized cars are on displayed on the 300 block of High Street. Come Food trucks, too!
Cars on High will continue on the third Thursday of the month, weather permitting, through October. Sponsored by Main Street Chestertown.
Chestertown Jazz Festival
If you’ve ever visited the Eastern Shore before, you know that it’s a hotbed for all kinds of musical talent! Jazz is an especially prominent genre here. Come and celebrate this colorful art form by attending the Chestertown Jazz Festival! It’s held at Wilmer Park and showcases a variety of new and established artists.
Sultana Downrigging Weekend
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. 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!
2nd Jigsaw Puzzle Contests at Brampton Inn
Here at Brampton Inn, we’re huge fans of Artifact Wooden Puzzles! What began as an addicting hobby for us became something our guests fell in love with, too. In March, we hosted our 1st. annual Jigsaw Puzzle Contest. Now we are planning #2 for November 16, 2019.
Book your stay, grab a partner, and put your skills to the test. You could win a brand new Artifact puzzle of your own!
Annual Chestertown Antiques Show and Sale
The annual Chestertown Antiques Show and Sale is a great opportunity to score a valuable, one-of-a-kind piece for your home! The best part about it? Proceeds benefit the Kent Association of Riding Therapy.
A Dickens of a Christmas
Always the first weekend in December. (December 4 and 5, 2020). Join the town for a weekend of festivities starting with a special First Friday throughout the Historic District. You will find carriage rides, hot beverages, fire pits, s’mores stations, and special entertainment to set the mood for a joyous holiday season.
Oyster Weekends at Brampton Inn
Oyster season is big here on Maryland’s Eastern Shore. We celebrate with our February Oyster Saturdays, which consist of complimentary oysters on the half-shell and a glass of bubbly (for guests)! Be sure to check it out on Saturdays at our Tea Time and Social Hour.
Be my Valentine!
February 7 through 15th, 2020. Come celebrate at the Brampton. A red rose and four house made chocolate truffles will be waiting for you and your Sweetie upon arrival. There will be Chocolate desserts every day in February.
FeBREWary in Maryland
FeBREWary is Maryland’s month-long celebration of all things craft beer. This month, you’ll find several fun beer-themed events on tap across the state. Keep an eye out for Patriot Acre Farm Brewery and Bull and Goat Brewery right here in our neck of the woods!
Jigsaw Puzzle Contests at Brampton Inn
Here at Brampton Inn, we’re huge fans of Artifact Wooden Puzzles! What began as an addicting hobby for us became something our guests fell in love with, too. In March, we host our annual Jigsaw Puzzle Contest. Book your stay, grab a partner, and put your skills to the test. You could win a brand new Artifact puzzle of your own!
Chestertown Tea Party Festival
The Chestertown Tea Party Festival is held every year on Memorial Day Weekend. This celebration of the town’s Revolutionary War history 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.
National Music Festival
The National Music Festival in Chestertown presents world-class concerts and provides affordable arts education and entertainment to aspiring musicians. Renowned classical musician and commentator Miles Hoffman usually makes an appearance!
Complete Your Trip With a Stay at Maryland’s Best Small-Town B&B!
Be close to all of the best events on the Eastern Shore of Maryland by booking your stay at one of our comfortable,
breakfast, bottomless homemade cookies, and access to a top-notch golf course. You’ll also love having access to all of Chestertown’s best outdoor adventures, local shopping, delicious dining, and rich history!