A Dickens of a Christmas

The 5th Annual Dickens of a Christmas is back on December 2-3, 2022! Join us for even more Victorian events and fun as popular favorites return after a Covid hiatus and new events debut. 

Dickens of a Christmas is hosted by Main Street Chestertown and all proceeds further Main Street’s work to make downtown Chestertown a vibrant community.

find out more about dickens' popular attractions

Beers & Bonfires

Listen to great music, warm your hands and toes around bonfires, and sample holiday beverages (of both a non-alcoholic and adult nature) during Beers & Bonfires. Bring your family and friends for a night of winter fun.

Horse Drawn Carriage Rides

Tour historic downtown as you've never seen it before from the back of a vintage horse-drawn carriage. Tips benefits KART (Kent Association of Riding Therapy), which helps children and adults with special needs enhance their social and developmental growth.

The American Rogues

This high-energy Canadian/American group has electrified audiences on three continents for years. They are known for their epic, multi-instrumental sound that crosses the musical landscape to include jigs, reels, hornpipes, ballads, originals, covers, soundtracks, patriotic and military music, Irish foot-stompers and more. Learn more by clicking "The American Rogues" above.

London Row

Get all of your holiday shopping done in one place! Vendors will be selling their wares in the antique Bank. All vendors are from the area and selling handmade products. Interested in being a vendor? Find out more information by clicking "London Row" above.

Run Like the Dickens 5k Run/Walk

Come ready to run or walk in your favorite holiday attire! Our charming downtown district will offer a Victorian-themed route, complete with Marley in the graveyard.

Children's Activities

There's even activities for Tiny Tim! Children's activities include caroling, a Flea Circus, pictures with Santa, a petting zoo, pony rides, and more! All activities during the Dickens Festival are family-friendly.

Holiday House Tour

The Holiday House Tour is back! Stroll iconic Water Street on the Chester River where our lovingly restored historic tour homes bring the gracious living of bygone days into the 21st century. Tickets go on sale October 15.

Holiday Tea

The Holiday Tea has returned with scrumptious treats and teas. This year's Tea is graciously hosted by Ms. Shelia Austrian. Tickets go on sale October 15.

2021 Event Schedule

Make sure to follow our Facebook page for the latest information and updates!

Interested in being a sponsor?

The only way Dickens of a Christmas is possible is through the generosity of our sponsors. Several sponsorship opportunities are available. Please see below for more information or contact office@mainstreetchestertown.org.