Downtown transforms into 1840s London Dec. 4–5 for the historic town’s most immersive holiday weekend yet.

Main Street Chestertown is proud to announce Urgo & Associates at 98 Cannon St. as the presenting sponsor for one of the Delmarva Peninsula’s most cherished holiday traditions. Dickens of a Christmas returns to Chestertown, MD on Friday, Dec. 4, and Saturday, Dec. 5, 2026, set to transform the historic downtown into a scene straight out of 1840s Victorian England—offering regional visitors an unforgettable kickoff to the holiday season.

“Dickens of a Christmas is a classically Chestertown event - full of good neighbors, friendly guests, hometown holiday cheer, and lively activity in our historic downtown,” said Dominique Ellis Falcon, executive director of Main Street Chestertown. “We are incredibly grateful for the presenting support of Urgo & Associates at 98 Cannon St. Their family fell in love with Chestertown and all this small town has to offer a long time ago, which is one of the reasons they’re thrilled to be bringing a new waterfront dining option and hotel to town. Supporting this time-honored festival is such a natural partnership, and we’re hoping to welcome everyone into their new facilities at 98 Cannon St. as soon as possible.”

Whether you're making a quick day trip across the Shore or settling in for a weekend getaway into one of Maryland’s oldest and most historic towns, visitors can expect live Celtic music, street performers, bonfires, hot oysters, carriage rides, an outdoor Victorian living room, and the annual seasonal cheer that will make even the stodgiest Scrooge merry. Be sure to dress up in your Victorian finest! 

To make this year’s festival more immersive than ever, festivalgoers will discover new attractions alongside fresh twists on classic holiday traditions:

• The Great Scrooge Off: On Saturday at 1:30 p.m., contestants of all ages can take the Main Stage to deliver their best “Bah, Humbug!” for local judges. The winner walks away with downtown spending money and an authentic top hat.  Advance sign-ups are encouraged via the Dickens website, though walk-up contestants will be permitted depending on participation numbers. 
• Ghost Scavenger Hunt: From 12:00 to 2:00 p.m. Saturday, keep an eye out for four wandering spirits—Past,Present, Yet to Come, and Jacob Marley—roaming the streets. Name a ghost when you spot them to collect unique Victorian keepsakes and complete your set, presented in partnership with cast members from the Church Hill Theatre’s upcoming production of  A Christmas Carol, which runs Dec. 18 - 20.  
• Dickens Destinations Across Downtown: Local storefronts and pop-up spots are turning into curated Victorian must-sees.Festivalgoers can sip artisanal Victorian hot chocolate, sample festive holiday cocktails, browse open-air literary markets, snap porch portraits, enjoy fortune wheel spins, get a tarot reading, or sit for a traditional palm reading at walkable stops throughout downtown.
• Expanded Family Fun at Tiny Tim’s Corner: Now relocated to the historic Courthouse Lawn, this family-friendly hub features live raptor and falconry demonstrations with the Maryland Raptor Conservancy, lawn games, and A Christmas Carol storytimes co-hosted with the Kent County Public Library inside the Garfield Center for the Arts lobby.
• Literary & Cultural Highlights: Enjoy a special Charles Dickens literary presentation by Washington College’s Dr. Katherine Charles, craft stations hosted by RiverArts inside the Heritage Village at The Bank, and an exclusive ghost storytelling experience by Rissa Miller.

“Dickens of a Christmas has become a regional beacon for holiday cheer, and as we approach our 10th anniversary next year, we’re focusing on what makes historic Chestertown such a special destination for our neighbors across the Eastern Shore,” added Ellis Falcon. “We want visitors to take in the grand spectacle, explore our historic brick avenues, step into our welcoming shops, and really experience the magic of our community.”

Returning Regional Favorites & Festival Nightlife

The festivities kick off Friday evening, Dec. 4, with late-night holiday shopping, food and beverage tents featuring craft brews and fireside oysters, horse-drawn carriage rides, and live stage performances by regional student choruses, jazz bands, and North America’s premier Celtic band, The Devil’s Brigade. At 7:00 p.m. Friday, the popular Fire Dancers return to stun audiences with flame feats and acrobatics.

Saturday, Dec. 5, brings the London Row and Heritage Village Artisans Markets, Wheelmen Antique Bicycles, the iconic Chestertown Farmers’ Market, and the beloved Dickens Victorian Tea at Christ United Methodist Church, alongside the popular Holiday Home Tour showcasing historic private residences. Main Stage musical highlights on Saturday include the O’McPub Band, the Baltimore Pipe Band, and a grand finale performance from The Devil’s Brigade.

Plan Your Visit

Much of the festival is completely free to explore. Tickets for select ticketed experiences (including the Victorian Tea,Home Tour, and special storytelling sessions) are available online.

Regional visitors can also jumpstart their holiday spirit the week prior during the Downtown Chestertown Association’s Holiday Parade and Santa’s Arrival on Friday, November 27, at 5:30 p.m.

For complete event schedules, tickets, costume guides, and map details, visit https://mainstreetchestertown.org/dickens-festival/.

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About Main Street Chestertown: 

Main Street Chestertown is dedicated to preserving, enhancing, and promoting historic downtown Chestertown. Through community collaboration, business advocacy, regional tourism promotion, and structural enhancement programs, the organization works to enhance the quality of life for residents and visitors alike. Additionally, Main Street Chestertown is proud to host its signature annual event the first week of each December, the Dickens of a Christmas Festival, which draws visitors from across the region to experience one of a kind holiday magic in the historic town. More information at mainstreetchestertown.org.