I thought I was visiting a standard Victorian street festival. I expected a few costumes, maybe some hot cider, and a quick walk-through.
Instead, a small Eastern Shore town quietly kicked off my entire holiday season.
I’d heard about Dickens of a Christmas in Chestertown, Maryland. Held the first weekend of December, it promises a Victorian-themed experience. But what I wasn’t prepared for was how fully the town commits to it, or how quickly a single weekend would shift me into Christmas mode.
Dickens of a Christmas in Chestertown, MD
High Street transforms into a Victorian marketplace for the first weekend of December | Photo: Better Living
Historic Chestertown doesn’t need to pretend. It dates back to 1706 and was founded as a working port on the Chester River, exporting tobacco and grain, and building ships. They even had their own Tea Party in 1774 to protest British taxation.
That history isn’t just in a museum; it’s visible in the bricks.
Eighteenth-century buildings line sidewalks that feel largely unchanged. This is exactly why “Dickens” works so well here. When a town already has this much real history, adding period costumes and hay bales doesn’t feel staged.
It feels like the town is remembering itself.
I spent both days of the festival staying at Brampton 1860, just four minutes outside of town. While Friday evening set the mood, Saturday was when everything clicked. I spent most of the day wandering High Street, moving slowly, and letting the atmosphere do the work.
An Era Layered on Top of Another
Victorian London comes to life at Dickens of a Christmas in Chestertown, MD | Photo: Better Living
What makes Dickens of a Christmas different is that Chestertown doesn’t have to fake the set design.
The downtown is the real thing. When Victorian costumes, vendor tents, and hay bales appear, it doesn’t feel like a recreation. It feels like one era gently layered on top of another.
Vendor tents line the closed streets. Hay bales turn into casual seating around firepits. Draft horses pull holiday carriages through the crowds.
The carriage ride offers unique views of Chestertown’s preserved 18th-century architecture | Photo: Better Living
I took one of the complimentary carriage rides sponsored by Brampton 1860, and it ended up being a highlight. The loop took me through the town’s most charming streets, past historic homes and under bare winter trees.
From the carriage, the preservation of the town becomes even more apparent. These are not recreations. These are buildings that have stood here for centuries, watching holidays come and go.
Oyster Stew, Figgy Pudding, and Firepits
Fresh oyster stew and figgy pudding warm festival-goers on cold December afternoons | Photo: Better Living
The food was delicious and comforting, which matters when you are outside for hours in December.
The Oyster Stew: A generous serving of fresh oysters in a creamy broth. I ate this sitting on a hay bale near a firepit, and it was exac
