Main Street Chestertown presents
Dickens of a Christmas
❦
Friday & Saturday · December 4–5, 2026
Downtown Chestertown
Step back into 1840s London as historic Chestertown becomes a holiday scene straight out of Dickens. Two days of music, Victorian fun, local shops and plenty of good cheer. And do come dressed like the dickens!
Downloadable map coming soon!
Follow Dickens of a Christmas on Social!
When
Fri, Dec 4 · evening
Sat, Dec 5 · all day
Where
Downtown Chestertown
Enjoy the festivities and stop into the local shops open all weekend.
I
Stave One
Friday Evening
Friday, December 4, 2026
Bonfires, oysters & good cheerAround Town
4:30-6:30PM
Kid Friendly Light Up the Night Activity
KidSpot - 200B High St.
Stop in and make your own working lantern to use throughout the evening!
5PM
Beverage & Food Tents Open
High Street
Beer, wine, oysters and victuals from local vendors.
5-8PM
Fabulous First Friday
Downtown shops
Shops stay open late for holiday shopping.
Free
5:30-8:30PM
Carriage Rides
Corner of N. Cross St. & Memorial Plaza
First come, first served. No tickets needed.
Suggested Donation
7PM
Fire Dancers
300 Block of High Street
Free
On the Main Stage
5PM
Opening Ceremonies
5:30PM
Garnet Elementary School Chorus
6PM
Kent County High School Jazz Band
6:30PM
River Voices
7:30PM
The Devil’s Brigade
Friday Night Spectacle
The Fire Dancers
As night falls on High Street, the fire dancers light up downtown. Free to watch. Find a spot and keep your scarf on.
❦
II
Stave Two
All Day Saturday
Saturday, December 5, 2026
Open All Day
8AM–12PM
Farmers' Market
Fountain Park
9AM–4PM
London Row Artisans Market
High Street
10AM–5PM
Beverage & Food Tents
Food from 11AM
11AM–3PM
Tiny Tim's Corner
Courthouse Lawn
In order of start timeAround Town
9AM–12PM
Santa's House
Fountain Park
Family
10AM–3PM
10AM–1PM,
2-4PM
Tarot Readings in the Victorian Parlor
The Bank
9:30AM–2:30PM
Wheelmen Antique Bicycles
High Street
11AM-3PM
Falconer Demonstration
Courthouse Lawn (Tiny Tim's Corner)
Family
11AM, 1PM
A Christmas Carol Story Time
Garfield Center lobby · with Kent County Library
Two readings of a children's A Christmas Carol.
Family
1PM
1PM
12-2PM
12–4:30PM
Carriage Rides
Corner of N. Cross St. & Memorial Plaza
First come, first served. No tickets needed but donations of $5 for children and $10 for adults are suggested.
Suggested Donation
5PM
A Dark Victorian Christmas: Ghost Stories for the Longest Nights with Rissa Miller
Kent Cultural Alliance Building. Limited seating available.
Ticketed Details coming soon →
On the Main Stage
10:30AM
O’McPub Band
11:30AM
Baltimore Pipe Band
12:15PM
O’McPub Band
1:30PM
Scrooge Off Contest
Your best "Bah, humbug!" · Sign-up coming soon
2:15PM
Baltimore Pipe Band
3:00PM
The Devil’s Brigade
New This Year for Saturday
Don't Miss
❦
Saturday · Main Stage
The Great Scrooge Off
1:30PM
Think you've got the Scroogiest "Bah, humbug!" in Kent County? Take the stage and give us your best Ebenezer for a panel of local judges. All ages welcome, from six to sixty.
Prize: Downtown Chestertown spending money and a top hat
Saturday · Sponsored by Church Hill Theatre
Ghost Scavenger Hunt
12PM - 2PM
Four spirits are wandering downtown. Spot a ghost, call them by name, and earn a Victorian keepsake. Collect all four!
- The Ghost of Christmas Past
- The Ghost of Christmas Present
- The Ghost of Christmas Yet to Come
- Jacob Marley
Pick up your ghost guide with your map at the Main Street table in The Bank on High St.
Reserve Your Seat
Tickets
Most of Dickens of a Christmas is free to wander. These experiences have limited space, so book ahead.
Dickens Victorian Tea
Saturday · 1PM · Christ United Methodist Church
Fragrant teas, finger sandwiches and sweets served on fine china, with festive music and warm conversation. Period attire encouraged, never required.
Holiday Home Tour
Saturday · 10AM–3PM
Step inside some of historic Chestertown's most beautiful homes, dressed for the season.
A Dark Victorian Christmas: Ghost Stories for the Longest Nights with Rissa Miller
Saturday · 5PM · Kent Cultural Alliance Building
Author, storyteller and folklorist Rissa Miller returns this year! Tickets coming soon, please note seating is limited.
SATURDAY ONLY • WANDER AROUND TOWN
Dickens Destinations
Downtown shops are joining the fun with their own bits of Victorian merriment. Follow the map, pop in, and spend a merry shilling or two.
Fezziwig's Fortune Wheel
Try your hand at Fezziwig's wheel and see what fortune the season holds.
Get a ticket for 1 free spin when you pick up your map at the bank on high street
Hot Chocolate, Victorian Style
Bespoke Chocolates
Warm up with a Victorian hot chocolate outside Bespoke's new chocolate shop.
A Victorian Book Stall
The Bookplate
Browse a Victorian open-air book market set up right out front.
A Dickensian Cocktail
Modern Stone Age
Raise a glass to the season with their take on a drink inspired by A Christmas Carol.
Sit for Your Portrait
Yarrow & Wren
Strike a pose in the Victorian selfie parlor on the front porch. Free, and very shareable.
Your Fortune in Your Palm
Bee Crafty Collectibles
A palm reader holds court in the front window. Your future awaits.
Tarot in the Parlor
The Bank
Step into a Victorian parlor for a tarot reading, 10AM–1PM & 2PM-4PM
Meet the Raptors
Maryland Raptor Conservancy
Come face to face with a hawk and an owl with Maryland Raptor Conservancy in Tiny Tim's Corner from 11am - 3pm on the Courthouse Lawn.
Make a Scrooge Money Pouch
Heritage village in The Bank
Stop by Chestertown RiverArts' table and design your own pouch for those coins you'll be hoarding for Christmas.
For the Little Ones
Tiny Tim's Corner
Saturday · Courthouse Lawn
New home this year: the Courthouse Lawn. Easy for families to find and a little away from the bustle.
- Falconer demonstration with an owl and a hawk
- Lawn games all afternoon
- Story time: two readings of A Christmas Carol with Kent County Library in the Garfield Center lobby
- Ghost hunt: older kids, find all four spirits!
Join the Scene
Dress Like the Dickens
❦
Half the magic is the crowd. Pull together your best Victorian look. Nothing fancy is needed, and a few pieces go a long way.
- Gents: top hat or flat cap, waistcoat, scarf and a long coat
- Ladies: long skirt, shawl or cape, gloves and a bonnet
- Anyone: plaid, velvet, lace and a pair of spectacles
With Gratitude
Thank You to Our Sponsors
Dickens of a Christmas wouldn't be possible without the businesses and neighbors who support it.
Stay in the Know
Get the Dickens Post
❦
Be the first to hear Dickens of a Christmas updates, plus news on Main Street Chestertown's other events all year long.
❦
"I will honour Christmas in my heart, and try to keep it all the year."
Charles Dickens, A Christmas Carol
Site Credit | Copyright © 2023 - 2026 Main Street Chestertown. All Rights Reserved.