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. Throughout the year there are also fun events, festivals, and classes you can attend to make your Maryland getaway even more transformative! There are lots to choose from, so we’ve listed some of our favorite Chestertown, MD events below for you!
Spring Events
Chestertown Tea Party Festival
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
For two weeks each June, musicians present over 35 concerts. Renowned classical musician and commentator Miles Hoffman usually makes an appearance!
Mount Harmon Wicomico Hunt Point to Point
A great day of spring horse racing plus antique carriage & hound parade, tailgate contest, food and open-air tavern and marketplace!
Mount Harmon National Revolutionary War Reenactment and Colonial Festival
Reenactment of the 1777 Philadelphia Campaign in the Chesapeake, British & Continental Encampments, Colonial Market Faire, hearth cooking, living history, and craft demonstrations, and don’t miss the Eastern Shore Food Court & General Foreman’s Tavern.
Summer Events
Frederick Douglass Juneteenth Celebration
Celebrate the history, culture, and achievements of African American life on the Eastern Shore of Maryland.
Pirates & Wenches Fantasy Weekend
Held just a short drive away from Brampton Inn (in Rock Hall), this fun festival offers immersive fun for everyone. Buccaneers and land-lubbers will rejoice in this themed, town-wide party every August.
Legacy Day
Celebrate local African American history. Enjoy a reception for honorees, a genealogy workshop, a concert and a dance party.
Cars on High
Every 3rd Thursday admire classic, exotic, antique, and customized cars 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.
Fall Events
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. Celebrate this colorful art form at Wilmer Park which showcases a variety of new and established artists.
Chestertown HP Festival
Grab your wand, hop on your broom, and come for a weekend of magic at the annual Chestertown HP Festival. Explore this colonial river town and join the fun, filled with spectacular activities. The HP Festival will delight both children and adults – wizards and witches alike.
Sultana Downrigging Weekend
This “tall ship and wooden boat festival” is so much more than meets the eye. Hobbyists love experiencing these stunning vessels in person, but this event also features live music, Dock Dogs competitions, and fireworks.
Mount Harmon Bull & Oyster Roast Fall Fundraiser
Enjoy a traditional Eastern Shore bull and oyster roast. With live Bluegrass music and live and silent auctions, it’s a good time for a great cause!
Mount Harmon Paper Chase
A great opportunity to ride at one of Maryland’s most beautiful historic sites, along the banks of the Sassafras River!
Winter & Holidays
A Dickens of a Christmas
Always the first weekend in December. Join the town for a weekend of festivities starting with a special First Friday throughout the Historic District. You’ll find carriage rides, hot beverages, fire pits, s’mores stations, and special entertainment.
Mount Harmon Open Air Yuletide Festival
Always the first weekend in December. Join the town for a weekend of festivities starting with a special First Friday throughout the Historic District. You’ll find carriage rides, hot beverages, fire pits, s’mores stations, and special entertainment.
Be My Valentine in February!
Come celebrate at the Brampton where we celebrate Love all month!
FeBREWary in Maryland
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!
Modern Stone Age Kitchen
Tired of processed food? These guys specialize in ancestral techniques to help you “Eat Like a Human.” Sign up early for their popular cooking classes and themed dinner events that nourish your body, educate, and entertain!
Crow Vineyard
Located just 10 minutes north of historic Chestertown, this award-winning winery is on our “must-stop” list. Sample their delicious blends and enjoy being surrounded by the rustic charm of a working vineyard and farm with grass-fed Angus beef raised on the property. Events range from blending seminars to themed pairings and even a 5k!
The Kitchen at the Imperial
A guest favorite for their approachable fine dining in a casual atmosphere! Come early at 6 pm for their relaxed wine tasting with small bites and then stay for dinner. The perfect evening out!
Wildly Native Flower Farm
What better way to spend your vacation than being surrounded by the beauty of this family-owned flower farm! They offer a wide variety of events on-site including floral arranging classes, teas, goat yoga, and more!
Chestertown Farmers Market
Enjoy the Farmers and Artisans’ Market in downtown Chestertown at Fountain Park every Saturday from 8 am until Noon.
Garfield Center for the Arts
A wonderful small-town theatre with a vibrant culture of performing arts featuring live music, musicals, dramas, and comedic stage productions.
The Mainstay
The Mainstay in Rock Hall is a wonderful small music venue offering year-round, weekly programs often featuring world-renowned players in a variety of genres.
River Arts Chestertown
A pillar of the art scene in Kent County, this lively and growing community exhibits local artists in a variety of mediums in their gallery in addition to hosting hands-on classes. Let your artistic spirit shine through on your next getaway!
Adkins Arboretum
We highly recommend savings at least one afternoon to visit this beautiful 400-acre native garden and preserve. Adkins Arboretum is a model for land management that strives to engage all people in conservation, appreciation, and enjoyment of the Chesapeake region’s native landscapes through education, recreation, art, and community events. Including 5 miles of trails, Adkins Arboretum is the only arboretum or public garden focusing solely on showcasing plants native to the Mid-Atlantic coastal plain and offers a robust program of events and classes to explore.
Photo credit Kellen McCluskey.
Mount Harmon Plantation
Once a prosperous tobacco plantation, this colonial-era Tidewater Plantation has been fully restored and open to the public for guided tours. In addition to the Manor House and supporting buildings, the estate features 5 miles of nature trails on over 200 acres teeming with wildlife and rare flora. Their Carriage House Education & Discovery Center offers special events throughout the year, including point-to-point horse racing and historical reenactments.
Chester River Packet Cruises
Experience the beauty of the Eastern Shore of Maryland cruising on this 65-foot classic yacht! The comfortable 1920-style tour boat offers two open-air decks, a climate-controlled salon, and limited table seating indoors and outdoors. Running May through Labor Day, you’ll want to get your tickets early for the public or themed special events cruises. A fun way to see the sights of historic Chestertown!