Illustration of a santa visit scene (A Dickens of a Christmas Weekend)
Christmas Markets

A Dickens of a Christmas Weekend

Set in Chestertown's Historic District, the festival celebrates the holiday season with carriage rides, live music, and entertainment. Visitors can encounter costumed characters roaming the streets and enjoy Victorian food and drink. The event also showcases themed vendors offering Victorian London and Dickens-inspired products.

What to Expect

Features Victorian food and drink, carriage rides, and costumed characters.

Event Details

Ages

All ages

Neighborhood

Downtown Chestertown

Organizer

Main Street Chestertown

Food & Drink

The event features Victorian food and drink.

Local Insight & Ratings

Family Friendly

🎄 🎄 🎄 🎄 ⚪ (4/5)

Best For

Fans of victorian holiday atmosphere

Vibe

Festive and historic

Energy Level

Moderate

Photo Friendly

High

Weather Sensitivity

Moderate

Location

Historic District
Chestertown, MD
21620

Tips & Advice

  • Sign up for the Dickens Post emails so you hear about returning favorites and new additions as soon as they're announced.
  • Stop by the Kent County Visitors Center on N. Cross Street for maps, brochures and tips on dining and shopping downtown.
  • Dress warmly for an evening on the streets of the Historic District, especially if you plan to take a carriage ride.
  • Come hungry and try the Victorian food and drink while you watch the costumed characters and live music.

Quick Actions

Frequently Asked Questions

What is there to do at Dickens of a Christmas?

The festival fills the Historic District with live music, carriage rides, costumed characters roaming the streets and other entertainment.

Is there food and drink?

Yes, Victorian food and drink is part of the festival.

Who runs the festival, and where does the money go?

Main Street Chestertown hosts it. All proceeds go toward Main Street's work to keep downtown Chestertown a vibrant community.

How can vendors or performers take part?

Organizers want vendors and entertainers with a Dickens or Victorian London theme. Email dickensfest@mainstreetchestertown.org with your product, brand or show.

How do I hear about what's new this year?

Sign up for the Dickens Post email list. Details on returning favorites and new additions are still to come.

Tags

Victorian Christmasholiday marketfamily friendlySanta visitstheaterfood trucksstreet foodtrain rideshorse drawn carriagescommunity celebration

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Always check the official website for the most current information.

We've done our best to keep details up-to-date, but event schedules, prices, and policies can change. For the latest updates, please visit the official website or contact the organizers directly. Christmas Events Near Me is an independent guide and isn't affiliated with the events we list.

Contributors & Updates

Last Updated: Oct 20, 2026
Original Submitter: Sep 17, 2025 The Christmas Events Near Me editorial team