Experience Historic Chestertown’s
Victorian Holiday Extravaganza
Step back into 1840’s London and experience the holiday season as Charles Dickens imagined it.
This two day event includes entertainment, home tours, food, book talks, merchandise, and more.
And don’t forget to come dressed like the dickens!
December 5 & 6, 2025
Main Street Chestertown welcomes thousands of residents and visitors
for its annual Dickens of a Christmas during this two-day celebration of the season.
“Christmas, and the end of the year, is definitely a time when people try their hardest to begin afresh, a good time; a kind, forgiving, charitable, pleasant time; when men and women seem by one consent to open their shut-up hearts freely.”
– Charles Dickens
Friday Schedule
Friday, December 5th, 2025
5 – 9pm, downtown Chestertown
Enjoy an evening filled with carriage rides, oysters, food vendors, beer, wine, and bonfires! We will have our opening ceremony and listen to KCHS Band, Garnet Elementary Chorus, Chester River Chorale, and end the night with a jam session from The Devils Brigade (formerly the American Rogues)!
Enjoy victuals from the following vendors:
In Jest
Happy Chicken Bakery
The Spicerie
Occasions Catering
Jim Thiess Oysters
Don’t forget to visit Santa!
Begin your holiday merriment on Friday evening with a visit and photo with Father Christmas himself!
On Saturday from 9AM to 12PM, Santa will be accepting wishlists at his house in Fountain Park before moving to Tiny Tim’s Corner in the afternoon to share a bit more Christmas cheer.
Saturday Schedule
December 6th, 2025
Step into the magic of Christmas Past as Saturday at the Dickens Festival comes alive with cheer! Enjoy a complimentary carriage ride through historic downtown, sip and savor your way through Victorian tea, and let the little ones delight in Tiny Tim’s Corner. Browse the artisan market for unique holiday treasures, then enjoy delicious food and drink while listening to the Main Stage acts as the town transforms into a scene straight from Dickens’ London.
Stage Schedule
10AM: O’McPub Band
11AM: Baltimore Pipe Band
12PM: Jimi Kinstle presents
1PM: O’McPub Band
2PM: Baltimore Pipe Band
3:30PM: The Devil’s Brigade
Run Like the Dickens 5K
7AM Registration
8AM Race Begins
Rain or Shine! Free Dicken’s Kids Dash (10 & Under) will take place just before the 5K begins. Start and finish near The Kitchen at the Imperial!
Spend the Day Among the Shopkeeps & Artisans
Spend a merry shilling or two and browse the stalls to fill thy satchel!
8AM – 12PM
Chestertown Farmers’ Market
8AM – 4PM
London Row Open with Artisans Market
9AM – 4PM
Heritage Village Open
Heritage Village Sponsors
Holiday House Tour
10AM – 2PM
10AM – 5PM
Beverage Tent Open
Serving beer, wine, hot cider, mulled wine, and non-alcoholic beverages!
11AM – 5PM
Food vendors open
Wheelman Antique Bicycles
10:30AM – 2:30PM
Tiny Tim’s Corner & Petting Zoo
11AM – 4PM
Enjoy a petting zoo, Victorian Bowling, Yard Games, Face Paint, Balloon Twister, and end with Ashton’s Musical Performances and a Magician!
Carriage Rides
12PM – 4:30PM
Step back in time and delight in a complimentary carriage ride in true Dickensian style! First come, first served!
Fortunes Await Within The Vault
Step into The Vault at Heritage Village (The Bank) for an encounter with destiny!
10AM – 2PM
Tarot Card readings
2PM – 4PM
Palm Readings
Victorian Tea
1PM – 3PM
Enjoy a proper English tea from Victorian servers.
“13 Unmerriest Monsters”
5:00PM-6:30PM
How much do you really know about the holiday season? …Have you taken precautions against the Yule Cat? Meow!
Get to know Mari Lwyd, a skeleton horse who challenges people in a battle of rhymes. How about the French whipping father, le Pere Fouttard? Locally, we must be on the lookout for the Belsnickel. Maybe you think your decor is up to snuff for inspection by The Yule Goat? Ready for Caga Tio, the festive holiday “log?”
Well, if you’re not prepared for all this, Krampus may be the best introduction for the true spirit of the season.
Join us for this darker look at holiday legends and lore presented by Rissa Miller, and discover the shady backend of the most wonderful time of the year ~ or as she likes to call it, a Creepy Little Christmas.
Rissa Miller is an editor, author, herbalist, seer, and storyteller. Her storytelling expertise stems from extensive research into the area of esoteric history, including ghosts, witchcraft, cryptids, and folklore. She often leads ghost tours and gives lively history talks.
How to dress like the Dickens
Join us in your very best
Victorian attire!
Thank You to Our Sponsors
Chestertown’s Annual Dickens of a Christmas would not be possible without the help from our Sponsors.
