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

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I thought I was visiting a standard Victorian street festival. I was hoping for some costumes, maybe some hot cider and a quick walk.

Instead, a small Eastern Shore town quietly kicked off my entire holiday season.

I heard Dickens of a Christmas in Chestertown, Maryland. Held on the first weekend of December, it promises a Victorian-themed experience. But I wasn’t prepared for just how committed the town is, or how quickly a single weekend would send me into Christmas mode.

Dickens of a Christmas in Chestertown, MD

Wide view of Dickens A view of a Christmas festival in the closed High Street, participants in Victorian costume, vendors' stalls, bales of hay, historic clock tower building in the background.
Wide view of Dickens A view of a Christmas festival in the closed High Street, participants in Victorian costume, vendors' stalls, bales of hay, historic clock tower building in the background. The High Street will be transformed into a Victorian market on the first weekend of December | Photo: Better Living

Historic Chestertown he doesn’t have 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. In 1774 they even had their own Tea Party to protest the British tax.

This history is not only in a museum; seen in the bricks.

Eighteenth-century buildings line the sidewalks, which feel largely unchanged. That’s why “Dickens” works so well here. When a town already has this real history, adding period costumes and bales of hay doesn’t feel staged.

The town seems to be remembering itself.

I spent the two days of the festival there Brampton 1860just four minutes outside of town. While he set the mood on Friday evening, everything clicked on Saturday. I spent most of the day wandering the High Street, moving slowly and letting the atmosphere do the work.

One era layered on top of another

Victorian couple in period costumes sitting on bales of hay at a Dickens of a Christmas festival, woman in red velvet coat with hat, man in black suit, Eastern Shore Fire BBQ tent and food vendors in background, authentic 1840's London setting.
Victorian couple in period costumes sitting on bales of hay at a Dickens of a Christmas festival, woman in red velvet coat with hat, man in black suit, Eastern Shore Fire BBQ tent and food vendors in background, authentic 1840's London setting. Victorian London comes to life in Dickens of a Christmas in Chestertown, MD | Photo: Better Living

What makes Dickens Christmas different is that Chestertown doesn’t have to fake the scenery.

Downtown is the real deal. With Victorian costumes, hawker stalls and bales of hay, it doesn’t feel like entertainment. It feels like one era is smoothly layered on top of another.

The vendor’s tent is located in the closed streets. Hay bales become informal seating around fireplaces. Draft horses pull holiday carriages through the crowd.

First-person view of horse inside red holiday wagon pulling down residential street in Chestertown with historic houses, passenger wearing Santa hat.
First-person view of horse inside red holiday wagon pulling down residential street in Chestertown with historic houses, passenger wearing Santa hat. Carriage rides in Chestertown’s preserved 18th century. It offers unique views of the architecture of the 20th century Photo: Better Living

I took one of the free carriage rides sponsored by Brampton 1860, and it was a highlight. The loop took me through the town’s most charming streets, past historic houses and under bare winter trees.

From the cart, the preservation of the village is even more evident. These are not entertainment. They are buildings that have been here for centuries, watching the holidays come and go.

Oyster Stew, Figgy Pudding and Firepits

Close-up of oyster stew in white takeout container, showing plump oysters in creamy broth with a wooden spoon, fig pudding visible in the background.
Close-up of oyster stew in white takeout container, showing plump oysters in creamy broth with a wooden spoon, fig pudding visible in the background. Oyster stew and fig pudding on cold December evenings | Photo: Better Living

The food was delicious and comforting, which matters when you’re out and about for hours in December.

  • Oyster stew: A generous serving of fresh oysters in a creamy broth. I ate this sitting on a bale of hay by a fire, and it was just what the cold evening called for.
  • Figgy Milk: Beyond the Christmas carol, I didn’t know what to expect. It was a dense and spiced cake, rich, complex and unmistakably festive.

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

A farmers market that fits the scene

Busy Chestertown Farmers Market with vendor tent street, shoppers browsing produce and produce on a winter's day above bare trees.
Busy Chestertown Farmers Market with vendor tent street, shoppers browsing produce and produce on a winter's day above bare trees. Chestertown’s year-round farmers market folds on Dickens Festival weekend

Chestertown Farmers Market It goes on Saturdays all year round. During the Dickens of a Christmas weekend, the market naturally fits into the festival.

There was a petting zoo that drew a constant crowd, with goats, ducks, a small rooster and even a Scottish Highland cow with long horns and a dark coat. Seeing the family interact with the animals added a warmth that goes beyond the Victorian theme.

Hands holding a colorful miniature rooster with red and black feathers at the petting zoo at the Dickens Festival
Hands holding a colorful miniature rooster with red and black feathers at the petting zoo at the Dickens Festival Farmers market petting zoo goats, ducks and even a small rooster | Photo: Better Living

This wasn’t just the clothes; it was really about bringing the people together around joy.

Quirky shops in historic buildings

The interior of the Twigs and Teacups store displays holiday merchandise including Christmas mugs, kitchenware, jams and ornaments with the shopkeeper browsing Victorian clothing
The interior of the Twigs and Teacups store displays holiday merchandise including Christmas mugs, kitchenware, jams and ornaments with the shopkeeper browsing Victorian clothing Local shops like Twigs and Teacups offer thoughtfully curated gifts and holiday items Photo: Better Living

Between moments of celebration, I popped into the shops of Chestertown. These are not tourist traps; they are independent and carefully guarded.

See also

  • Walnut and wool: Decorated with vintage Christmas trees and pressed tin ceilings.
  • Custom made chocolates: Handmade truffles with chocolate decorations hung under a silver tree.
  • Book plate: A reminder of why independent bookstores matter, with floor-to-ceiling shelves and that unmistakable smell of books.
  • Branches and Teacups: The perfect mix of holiday gifts, kitchenware toys, and everything in between.
  • Coco’s Pet Center: Specializing in unique, fun, local, artisan pet products.

Why Brampton 1860 was the perfect base

Historic brick Brampton 1860 Inn decorated with Christmas lights and wreaths at sunset, with a dusting of snow on the front lawn and a pink sunset sky behind the building.
Historic brick Brampton 1860 Inn decorated with Christmas lights and wreaths at sunset, with a dusting of snow on the front lawn and a pink sunset sky behind the building. Brampton 1860 offers the perfect retreat after a day at the festival Photo: Better Living

in the inn Brampton 1860 It was the perfect match for Dickens of Christmas. After hours in the cold, I retreated to my cabin a few minutes later. It was also fun to see most of the Palace guests “dressed like chicks” during the weekend.

On Saturday evening, I left the festival around 4:00 pm to be back in time for tea. Over poinsettia cocktails and freshly baked cookies from Chef Carol at the Manor House, I talked about my favorite moments of the day.

Cozy 1860s Brampton library room with floor-to-ceiling bookshelves, leather furniture, wood-burning fireplace and large Christmas tree decorated with red ribbons
Cozy 1860s Brampton library room with floor-to-ceiling bookshelves, leather furniture, wood-burning fireplace and large Christmas tree decorated with red ribbons Manor House Library in Brampton 1860 | Photo: Better Living

The next morning, at breakfast, the guests exchanged stories of their stay at Dickens: what they bought, what they ate and their plans for the coming year. The transition from public celebration to private comfort gave the weekend a perfect pace.

âž¡ See our full Brampton 1860 review

Why is it stuck with you?

Festival goers in period costumes sitting on old Victorian couch and bales of hay near fireplace, bulldog wearing Christmas jumper in foreground
Festival goers in period costumes sitting on old Victorian couch and bales of hay near fireplace, bulldog wearing Christmas jumper in foreground Thick bales, fireplaces and sofas also create places to gather throughout the festival Photo: Better Living

I came to a festival in Victoria and left talking about starting a new tradition.

Logistics does not stop there. What I am left with is the sense of a small town celebration that welcomes the visitor into the experience.

Costumes are fun. It’s comfort food. It’s real history. 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: Christmas Dickens

Woman in Victorian dress posing with Father Christmas character on a decorated sleigh at night in front of a Dickens Christmas festive banner
Woman in Victorian dress posing with Father Christmas character on a decorated sleigh at night in front of a Dickens Christmas festive banner Victorian characters bring the festival to life Historic Chestertown, MD | Photo: Better Living
  • Place: Downtown Chestertown, Maryland (High Street).
  • When: The first full weekend of December.
  • Cost: Free to join. Bring money for food vendors and the market.
  • Where to stay: Brampton 1860 (Book in advancebecause it’s a popular weekend).
  • Don’t miss: Carriage Rides and Oyster House.

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