One of Maryland’s Quirkiest Towns Is Still Flying Under the Radar

Looking for a quirky town in Maryland where art, history, and a special youthful energy come together in perfect harmony? Chestertown has you covered. This town may have been founded in the 18th century, but locals know how to blend tradition with modern flair without sacrificing the historical charm of its preserved colonial-era architecture. 

Where Is Chestertown, and Why Is It So Unique?

This historic town is located on the east side of Maryland by Chesapeake Bay. Founded in 1706, Chestertown was one of the royal ports of entry and, as a result, gained considerable early wealth, which the town still reflects today. Known as one of the best places in Maryland to find authentic historical homes, this town also established Washington College, the tenth-oldest chartered college in the United States. This has meant that youthful influences have been able to remain here over the years, creating a fascinating community that feels like a tiny village but operates like a well-established town, with a flourishing historic district, and independent boutique shops alongside cafes and bookstores. 

Art and history are at the core of this unique small town in Maryland. Galleries and studios sit tucked away in corners, some even housed in buildings that seem out of colonial times. Festivals are common on the red brick-lined streets, and the historical district (especially the old port area) is beautiful to visit at any time of year. In this area, you’ll find the Bordley History Center, where you can explore museum exhibits, dig through archives, and find guided tours. 

The Quirky Events That Define This Town

Because Chestertown is a college town, there are often festivals and other events that fill up the calendar. Some could be related to sports, art, or even Harry Potter (a festival that is gaining traction with each passing year due to its popularity among students), but two festivals in particular are the most well-known.

The Chestertown Tea Party Festival

Hosted in May on Memorial Day weekend, this festival reenacts when tea was thrown into the Chester River in 1774 to protest the British, following Boston's lead the year before. The Schooner Sultana (a replica of an original 1767 ship) is part of the reenactment, and the reenactors dress in costume and stick to a script to the delight of tourists and locals alike. 

A Dickens of a Christmas Festival 

A two-day event in early December, this festival transforms the area into a town seemingly straight out of a Victorian Christmas tale. In fact, it’s meant to take people back to 1840s London during the time of Charles Dickens’ stories. There are themed characters in costume, performers who sing and dance, tours of decorated historic homes, a 5K run (cleverly named, ‘Run Like The Dickens’), and vendors who sell crafts and art, in addition to food and drink.

Why This Unique Small Town in Maryland Still Flies Under the Radar

It makes very little sense that Chestertown isn’t more popular, especially given its early favor with settlement (and wealth) and establishment of the old college. But, nowadays it seems that its location has proven to be the problem, too out of the way for “normal” tourists who want to visit the bigger cities in Maryland that sit closer to DC or the more popular ocean towns that are located closer to Assateague Island. 

Although tourists are clearly missing out, locals seem quite happy to keep Chestertown as a hidden gem in Maryland for themselves. Besides the quirky festivals and fun historical touches, the area reaps the benefits that towns along the Chesapeake Bay do, mainly with regard to dining (hello seafood), watersports, and peaceful natural landscapes. 

Perhaps some of Chestertown’s quirk comes from the very fact that it isn’t popular with tourists? The booming youthful art scene feels unrestrained from outside influences, and the tight-knit community genuinely enjoys their fun festivals and keeping their little town a pristine slice of history. But now that the secret is out, you should visit Chestertown, one of the most charming hidden gem towns in Maryland, during one of their festivals (just make sure to be respectful and don’t step on the toes of the locals or students)!