Updated for 2026
Christmas in Maryland feels different on the Eastern Shore. Here in Chestertown, the holidays move at a gentler pace, with carriage rides along High Street and fresh greenery decorating historic homes. At the end of the day, a fire is waiting in your room.
We’ve gathered our favorite 2026 holiday events, along with the festive celebrations and packages we host here at Brampton 1860. If you already know which weekend you want, choose your favorite room for a holiday stay at Brampton 1860, and we’ll take care of the rest.
2026 Christmas Events in Maryland: Dates to Know
Some of our favorite Christmas events in Maryland take place right here on the Eastern Shore. Here’s what’s happening from Thanksgiving weekend through New Year’s Day.
- Nov 25–29: Ultimate Eastern Shore Thanksgiving Getaway | Brampton 1860
- Nov 28: Shop Small, Rock Hall | Rock Hall
- Dec 4 & 5: Dickens of a Christmas | Downtown Chestertown
- Dec 4–20: A Sherlock Carol (weekends) | Garfield Center for the Arts
- Dec 5: Santa Arrives and Crab Basket Tree Lighting | Rock Hall
- Dec 5 & 6: Yuletide Festival & Holiday Marketplace | Mount Harmon, Earleville
- Dec 19: Christmas Show at The Mainstay | Rock Hall
- Dec 24–27: Home for the Holidays | Brampton 1860
- Dec 30 – Jan 1: Cheers to New Years! | Brampton 1860
The first weekend of December is the one to circle. Dickens, Mount Harmon, and Rock Hall’s tree lighting all land Dec 4–6, and A Sherlock Carol opens that Friday, too.
What Is Dickens of a Christmas in Chestertown?
Dickens of a Christmas is Chestertown’s two-day Victorian celebration. It returns Dec 4–5, 2026, and downtown Chestertown takes on the sights and sounds of Victorian London.
Expect horse-drawn carriage rides, carolers, street performers, a holiday home tour, book talks, and local food vendors. Costumes are encouraged, so don’t be surprised by a top hat or two. Of all the Christmas festivals in Maryland, it’s the one we’d plan a whole weekend around. The full 2026 schedule will be posted on the Dickens of a Christmas page as details are announced.
Our tip: Arrive Thursday so you can stroll into Friday evening without watching the clock. Save Saturday for shopping along High Street and a long lunch downtown.
Where Else Can You Celebrate the Holidays Near Chestertown?
Mount Harmon’s Yuletide Festival and Rock Hall’s holiday weekends are both worth the short drive. Back in town, the Garfield Center adds live theater to the season.
Yuletide Festival & Holiday Marketplace at Mount Harmon
Dec 5 & 6 | 11am – 3pm
Historic Mount Harmon in Earleville hosts its Yuletide Festival the same weekend as Dickens, about 45 minutes north of us. Volunteers craft Williamsburg-style wreaths and arrangements from boxwood, magnolia, holly, and pine grown on the property. Tour the decorated manor house, then warm up with hearth cooking and wassail in the colonial kitchen.
Admission is around $10 per person, and children under 12 get in free. Reserve tickets through Mount Harmon’s Yuletide Festival page.
Holiday Weekends in Rock Hall
About 20 minutes from Chestertown, the waterfront town of Rock Hall spreads its holiday season across several weekends. It starts on Nov 28 with Shop Small, Rock Hall, when local shops welcome holiday shoppers and carriage rides roll through town. If you’re staying with us for Thanksgiving, it’s an easy outing to add to your holiday weekend.
On Dec 5 at 6pm, Santa arrives by boat at the public bulkhead, followed by the crab basket tree lighting on Main Street. It’s about as Eastern Shore as Christmas gets. The Mainstay closes out the season with its Christmas show on Dec 19 at 7:30pm.
A Sherlock Carol at the Garfield Center
Weekends, Dec 4–20
The Garfield Center for the Arts closes its 2026 season with A Sherlock Carol by Mark Shanahan, a crossover of two Victorian classics. A grown-up Tiny Tim asks Sherlock Holmes to investigate Ebenezer Scrooge’s death. Performances run in the Prince Theatre, a 1928 Art Deco movie house at 210 High Street.
Opening night falls on Dickens Friday, making it easy to enjoy both events during one visit. The theater is right in downtown Chestertown, just a short drive from our inn. Find showtimes and tickets on the A Sherlock Carol page.
How Does Brampton 1860 Celebrate the Holiday Season?
The holidays are especially memorable here at Brampton 1860. From our traditional Thanksgiving celebration to Christmas dinner and New Year’s Eve, we’ve planned a few special ways to celebrate.
Every room and cottage has a fireplace or wood stove, perfect for warming up after a day exploring Chestertown.
Explore our holiday packages and specials for more details.
Ultimate Eastern Shore Thanksgiving Getaway (Nov 25–29)
Our four-night Thanksgiving getaway begins with champagne, locally handcrafted chocolates, and live music to welcome you. Thanksgiving dinner is a full traditional feast, including a glass of Crow Vineyard wine and live music throughout the evening. The package is $265 per couple plus lodging and tax, and includes 15% off your four-night stay.
Home for the Holidays (Dec 24–27)
Christmas Eve begins with a fire in the library and the house dressed for the season. On Christmas Day, we serve a three-course dinner with a glass of Crow Vineyard wine and live music. For a memorable Christmas dinner in Maryland, join us at Brampton 1860. We’ll take care of the cooking and cleanup so you can simply enjoy the celebration.
Each morning begins with our three-course breakfast featuring locally sourced ingredients. In the afternoon, enjoy homemade cookies and holiday treats at tea time. The three-night package is $245 per couple plus lodging and tax, and includes 10% off your stay.
Cheers to New Years! (Dec 30 – Jan 1)
Celebrate New Year’s Eve aboard the historic Chester River Packet with a cruise featuring cheeses, desserts, and live music. Then return to Brampton for dinner, followed by a midnight countdown and champagne in the Salon de Lumière. The two-night package is $295 per couple plus lodging and tax, and includes 10% off your room. Reservations are required at least four days in advance.
How Should You Plan a Christmas Getaway in Maryland?
We recommend at least two nights for a Christmas getaway on Maryland’s Eastern Shore. If you’re visiting the first weekend of December, consider staying three. You’ll have time to enjoy Dickens of a Christmas, Mount Harmon’s Yuletide Festival, and Rock Hall’s tree lighting without rushing from one event to the next.
When guests ask about our favorite Christmas towns in Maryland, Chestertown and Rock Hall always top our list.
Chestertown is an easy holiday getaway from Baltimore, Washington, DC, and Philadelphia (approx. 1.5–2 hours away). Guests also come from New York City (about 3 hours away), making the Eastern Shore a lovely alternative to the city’s holiday crowds.
For a cozy Christmas stay, we often recommend our cottages. Mulberry has a Japanese soaking tub on its screened porch, and every cottage has its own fireplace or wood stove.
Between events, there’s plenty to fill a quiet afternoon. Our guide to things to do on the Eastern Shore this winter covers oyster season, tundra swans at Eastern Neck, and more.
Frequently Asked Questions About Christmas in Maryland
When is Dickens of a Christmas 2026 in Chestertown?
Dickens of a Christmas takes place Dec 4–5, 2026, in Chestertown’s historic downtown. Main Street Chestertown posts the full schedule on its website as the festival gets closer.
What fun Christmas activities in Maryland are near Chestertown?
Mount Harmon’s Yuletide Festival in Earleville runs Dec 5–6, about 45 minutes away. Rock Hall, 20 minutes from Chestertown, hosts Shop Small on Nov 28 and Santa’s arrival by boat on Dec 5. Downtown, the Garfield Center for the Arts stages A Sherlock Carol on weekends Dec 4–20.
Is Brampton 1860 open over Christmas?
Yes. We welcome guests through the holidays, and our Home for the Holidays package runs Dec 24–27 with Christmas dinner included. Every room and cottage at our Maryland bed and breakfast has a gas fireplace or wood stove.
How many nights should I stay for Christmas events in Chestertown?
We recommend at least two nights for a holiday getaway in Chestertown. For the first weekend of December, three nights gives you time to enjoy Dickens of a Christmas, nearby holiday markets, and Rock Hall’s festivities. Tip: A three-night stay gives you time to truly relax and unwind, no matter when you book.
Spend Christmas in Maryland With Us at Brampton 1860
Christmas on Maryland’s Eastern Shore brings festive traditions, and we love our small-town charm, which gives you time to enjoy the season together. Spend your days exploring Chestertown’s holiday events, then return to Brampton 1860 for a cozy fire and a peaceful evening.
Planning a winter escape for two? Our guide to romantic things to do in Maryland shares a three-day plan for couples.
Book your holiday stay at Brampton 1860 and let us take care of the rest.
Happy holidays from David, Hilari, and all of us at Brampton 1860.