Lifestyle November 29, 2023

A Dickens of a Christmas Weekend in Chestertown Event Spotlight

As the festive season approaches, Chestertown is gearing up for a magical celebration that promises to transport residents and visitors alike to the enchanting world of Charles Dickens. From December 1st to 3rd, 2023, Coldwell Banker Chesapeake Real Estate is set to shine a spotlight on the town’s annual “A Dickens of a Christmas” weekend. Join us as we unwrap the details of this joyous event and invite you to experience the warmth of the season with us at Coldwell Banker.

Friday, December 1st – Festival Opening

Kickstarting the weekend on Friday, December 1st, Coldwell Banker Chesapeake Real Estate invites you to an open house. Join us starting at 5 pm for complimentary refreshments as we celebrate the holiday season together.  Many other events will be happen this evening as well – Enjoy an evening filled with oysters, food vendors, beer, wine, and bonfires! Listen to KCHS Jazz Band, Garnet Elementary Chorus, River Voices, and end the night with a jam session from Dell Foxx Company!  Also opening night for of Kate Hammill’s Little Women at the Garfield Center of the Arts.  Many of Chestertown’s downtown businesses will be open late.

Saturday, December 2nd – A Day of Festivities:

7 AM – 9 AM: Run Like the Dickens! 5K Run/Walk and Kids’ Fun Run:

Start your Saturday on an active note by participating in the “Run Like the Dickens!” event. The 5K Run/Walk and Kids’ Fun Run will commence and finish near The Kitchen at the Imperial. This invigorating activity is not only a great way to stay active but also an opportunity to soak in the festive atmosphere that Chestertown exudes during the holiday season. There is still time to register!

Holiday House Tours

Following the morning run, Chestertown invites you to explore the exquisite charm of festively adorned homes with the Holiday House Tour. Wander through the historic streets and marvel at the enchanting decor that beautifully captures the spirit of the holidays. This self-guided tour offers a unique glimpse into the warmth and creativity of Chestertown’s residents.

Children’s Activities at Park Row:

For families with little ones, Park Row becomes a hub of excitement with a range of children’s activities. From face painting to holiday crafts, there’s something for every young reveler. The festive ambiance of Park Row ensures that the younger members of the community can create joyful memories that will last a lifetime.

Santa’s House Open in Fountain Park:

As the day unfolds, Fountain Park opens its doors to welcome children of all ages to Santa’s House. Step into the magical world of Santa Claus and share your holiday wishes with the jolly old man himself. The picturesque setting of Fountain Park adds an extra touch of magic to the experience, making it a must-visit for families and individuals alike.


Throughout the Dickensian weekend, Chestertown transforms into a living storybook, weaving together the magic of the season with the warmth of community. From the spirited run through town to the Holiday House Tour and the joyous activities for children, the festivities are abundant. Coldwell Banker Chesapeake Real Estate is proud to be a part of this celebration, and we invite you to join us in creating cherished memories and spreading holiday cheer throughout downtown Chestertown. We look forward to welcoming you to our open house on December 1st and sharing in the joy of “A Dickens of a Christmas” weekend!