I thought I was visiting a standard Victorian street festival. I was expecting some costumes, maybe hot cider, and a quick walkthrough.
Instead, a small town on the Eastern Shore quietly kicked off my entire holiday season.
I was hearing about Dickens at Christmas in Chestertown, Maryland. Held during the first weekend of December, it promises a Victorian-themed experience. But what I wasn’t prepared for was how enthusiastic the town would be about Christmas, or how quickly just one weekend would send me into Christmas mode.
Dickens’ Christmas in Chestertown, Maryland
The High Street turns into a Victorian market on the first weekend of December | Photo: Better Livinghistoric chester town No need to pretend. Its history dates back to 1706, when it was established as a working port on the Chester River, exporting tobacco and grain, and building ships. It even had its own Tea Party in 1774 to protest British taxation.
Its history is not limited to museums. You can see it in the brick.
18th-century buildings line the largely unchanged sidewalks. This is exactly why “Dickens” works so well here. When a town already has so much real history, adding period costumes and hay bales doesn’t feel staged.
It feels like the city is remembering itself.
I spent both days of the festival staying here brampton 1860only 4 minutes from town. While Friday night set the tone, it was Saturday when everything fell into place. I spent most of the day walking around the High Street, moving slowly and letting the atmosphere take its course.
era after era

Victorian London comes to life at Dickens of a Christmas in Chestertown, Maryland. Photo: Better lifeWhat makes Dickens of Christmas different is that Chestertown doesn’t have to fake the set design.
Downtown is real. Victorian costumes, vendors’ tents, and hay bales make it hard to believe it’s recreation. It feels like one era is gently layered on top of another.
Vendor tents line the closed streets. Hay bales transform into casual seating around the fireplace. Draft horses pull a tourist carriage through the crowd.

A horse-drawn carriage ride provides unique views of Chestertown’s preserved 18th-century architecture. Photo: Better lifeWe took a free horse-drawn carriage ride sponsored by Brampton 1860, which ended up being a highlight. This loop took us through the town’s most charming streets, past historic homes, and under bare winter trees.
The preservation of the town is even more apparent when viewed from a horse-drawn carriage. These are not recreations. These buildings have stood here for centuries, watching the holidays come and go.
Oyster stew, figgy pudding, fire pit

Fresh oyster stew and fig pudding warm festival goers on a cold December afternoon | Photo: Better LivingThe food was delicious and comforting. This is important when you’re outside for hours in December.
- Oyster stew: A creamy soup with plenty of fresh oysters. I ate this sitting on a bale of hay near the fireplace and it was exactly what the cold afternoon needed.
- Fig pudding: Beyond a Christmas carol, I had no idea what to expect. It was a rich, spiced cake, rich, complex, and undeniably festive.
Time slows down as you eat warm stew in a hay bale by the fireplace while watching people dressed in Victorian costumes pass by.
Farmers market tailored to the occasion

Chestertown’s year-round farmers market integrates seamlessly into Dickens Festival weekendChestertown Farmers Market It runs on Saturdays throughout the year. The markets naturally become festive during Dickens’ Christmas weekend.
The petting zoo, which featured goats, ducks, miniature roosters and even a Scottish Highland cow with long horns and shaggy fur, always drew crowds. Watching the family interact with the animals added warmth beyond the Victorian theme.

Farmers Market’s petting zoo features goats, ducks, and even a mini rooster | Photo: A Better LifeThis isn’t just about costumes. It was about the town coming together around something really fun.
A quaint shop in a historic building

Local shops like Twigs and Teacups offer a selection of gifts and holiday items. Photo: Better lifeIn between festivals, I wandered into the Chestertown store. These are not tourist traps. They are independent and carefully selected.
See also


- Walnut and wool: Decorated with vintage Christmas trees and pressed tin ceilings.
- Custom made chocolates: Handmade truffles are displayed beneath a silver tree hung with chocolate ornaments.
- Book plate: It’s a reminder of why independent bookstores, with their floor-to-ceiling shelves and unmistakable book scent, are so important.
- Twig and teacup: It’s the perfect combination of everything from holiday gifts and kitchenware to toys.
- Coco Pet Center: We specialize in unique, fun, local, handcrafted products for pets.
Why the Brampton 1860 is the perfect bass

Brampton 1860 offers the perfect retreat after a day at the festival | Photo: Better LivingAccommodation brampton 1860 It was the perfect combination for Christmas Dickens. After spending hours in the cold, we were able to return to our cottage, which was only a few minutes away. It was also fun to see most of the Manor House guests “dressing like Dickens” throughout the weekend.
Saturday afternoon I decided to leave the festival around 4pm and head back for tea time. Over poinsettia cocktails and freshly baked cookies from Chef Carol at the Manor House, we talked about our favorite moments from the day.

Manor House Library in Brampton 1860 | Photo: Better LivingAt breakfast the next morning, guests talked about their memories of Dickens, what they bought and ate, and their plans for next year. The transition from public celebration to private comfort gave the weekend a perfect rhythm.
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Why does it stay in your heart?

Hay bales, fireplaces, and even sofas create a casual gathering spot during the festival | Photo: Better LivingI came to the Victorian Festival and left talking about starting new traditions.
Logistics should not be long. What sticks in my memory is the small town festival feel that welcomes visitors into the experience.
Costumes are fun. Food is comforting. Its history is true. But it’s the warmth and ease of the community that makes the weekend feel so meaningful.
I’m already planning to return next year.
🎄 Plan your trip: Dickens’ Christmas

Victorian characters bring the festival to life throughout historic Chestertown, Maryland. Photo: Better life- position: Downtown Chestertown, Maryland (High Street).
- when: The first full weekend of December.
- Fee: Participation is free. Bring cash if you go to the grocery store or market.
- Where to stay: Brampton 1860 (Please book earlyas it is a popular weekend).
- Don’t miss: Horse-drawn carriage rides and oyster stew.
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Source: Better Living – onbetterliving.com
