Forget the Hallmark Movies: This Real-Life Victorian Christmas Festival is Better | Better Living

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

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

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.

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

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 exactly what the cold afternoon called for.
• The Figgy Pudding: Beyond the Christmas carol, I had no idea what to expect. It turned out to be a dense, spiced cake that was rich, complex, and unmistakably festive.

Eating hot stew on a hay bale by the fire, watching people in Victorian costume walk by, has a way of slowing time.

A Farmers Market That Fits the Scene

Chestertown’s Farmers Market runs year-round on Saturdays. During Dickens of a Christmas weekend, the market folds naturally into the festival.

There was a petting zoo drawing steady crowds, featuring goats, ducks, a mini rooster, and even a Scottish Highland cow with long horns and a shaggy coat. Watching families interact with the animals added a warmth that went beyond the Victorian theme.

This wasn’t just about costumes; it was about the town coming together around something genuinely joyful.

Quaint Shops in Historic Buildings

Between festival moments, I stepped inside Chestertown’s shops. These aren’t tourist traps; they are independent and carefully curated.

See also

• Walnut and Wool: Decorated with vintage Christmas trees and pressed tin ceilings.
• Bespoke Chocolates: Handmade truffles displayed beneath a silver tree hung with chocolate ornaments.
• Book Plate: A reminder of why independent bookstores matter, with floor-to-ceiling shelves and that unmistakable smell of books.
• Twigs and Teacups: A perfect mix of holiday gifts, kitchenware to toys, and everything in between.
• Coco’s Pet Center: Specializing in unique, fun, local, handmade products for pets.

Why Brampton 1860 Was the Perfect Base

Staying at Brampton 1860 turned out to be the perfect pairing for Dickens of Christmas. After hours in the cold, I could retreat to my cottage just minutes away. It was also fun to see most of the guests in the Manor House “dressed like the dickens” throughout the weekend.

On Saturday afternoon, I left the festival around 4 PM to make it back for tea time. Over Poinsettia cocktails and Chef Carol’s fresh-baked cookies in the Manor House, I talked through favorite moments from the day.

The next morning at breakfast, guests traded stories of their time at Dickens – what they bought, what they ate, and their plans for next year. That shift from public celebration to private comfort gave the weekend a perfect rhythm.

➡ See our full Brampton 1860 review

Why It Sticks With You

I came for a Victorian festival and left talking about starting a new tradition.

The logistics aren’t what linger. What stays with me is the feeling of a small town celebration that welcomes visitors into that experience.

The costumes are fun. The food is comforting. The history is real. But it’s the warmth and ease of the community that makes the weekend feel meaningful.

I’m already planning my return next year.

🎄 Plan Your Trip: Dickens of a Christmas

• Location: Downtown Chestertown, Maryland (High Street).
• When: The first full weekend of December.
• Cost: Free to attend. Bring cash for food vendors and the market.
• Where to Stay: Brampton 1860 (Book well in advance, as this is a popular weekend).
• Don’t Miss: The Carriage Rides and the Oyster Stew.