Updated for 2024. All the holiday events in and around Chestertown, Maryland, truly make the Eastern Shore special. It’s the perfect destination for those seeking a traditional holiday retreat. We love celebrations that take place right outside our door at Brampton 1860.
Learn how you join in the festivities of our charming historic town of Chestertown, Maryland’s holiday events—whether it’s a quick weekend getaway or a midweek escape.
A Brampton Thanksgiving Getaway
Nov 27 – Dec 1, 2024
Indulge in an authentic New England Thanksgiving with our Ultimate Eastern Shore Thanksgiving Getaway package from November 27 – December 1, 2024. Enjoy champagne and local chocolates upon arrival before celebrating with a lavish traditional Thanksgiving dinner with all the trimmings and a bottle of Crow Vineyard wine.
Next, treat yourself with the included $60 Chestertown Cash Gift Certificate and shop downtown at the charming boutique shops. A three-course breakfast with mimosas will be served daily, along with homemade cookies and other treats at tea time. What an incredible opportunity for a warm and inviting Thanksgiving celebration full of love, laughter, and endless memories.
Dickens of a Christmas
Dec 6 & 7, 2024
Secondly, join us this year for the annual Dickens of a Christmas and participate in downtown holiday activities. There’s so much to do and see at Chestertown’s Victorian Holiday Extravaganza!
Check out the live events from carolers, street performers, and even traditional Celtic music from the American Rogues. Or, perhaps, take a ride in a horse-drawn carriage, try delicious food from local vendors, and get your Christmas shopping done surrounded by the beauty of the holiday. There’s no better way to get into the holidays than immersing yourself in the Victorian aesthetic, just like the Christmases of old!
Yuletide Festival and Holiday Marketplace
Dec 7 & 8, 2024 | 11am – 3pm
In addition, you’ll want to head to Mount Harmon for some old-fashioned holiday revelry and find that extra-special gift at the Yuletide Festival & Holiday Marketplace, chock-full of homemade wreaths, seasonal decor, and other artisanal crafts. Experience hearth cooking as they would have in times past and experience a tour of the historic manor house. It’s the perfect way to connect Christmases from the past with our modern celebrations to see that, in some ways, they aren’t so different. Reserve tickets now for this adorable holiday marketplace in Maryland!
Célébration de Noël!
Dec 21 | 3-6pm
Step into the holiday magic of a bygone era at Brampton’s Célébration de Noël! It’s a winter wonderland. River Voices perform beloved holiday carols and enjoy horse-drawn carriage rides throughout the estate’s property. Shop at our holiday market under the sparkling Christmas lights, where vendors will offer drinks, food, and artisanal items.
Christmas Dinner at Brampton
Dec 23-26, 2024
Certainly the premier event of the season and one of our favorites, Christmas dinner at Brampton 1860 is the ultimate holiday escape. Join us on Christmas day with the halls fully decked out in boughs of holly and other seasonal decor inside and out! Sit down for three delicious courses of the finest Brampton has to offer, served with a bottle of wine. Spend quality time with friends, family, and other guests to celebrate the reason for the season. Learn more about the details of our Home for the Holidays package.
Ring in the New Year at Brampton
Dec 30, 2024 – Jan 1, 2025
Finally, experience an elegant getaway to ring in the New Year with our Cheers to New Years! Package. Choose either a 2-night or 3-night stay in one of our luxurious rooms. Sip on champagne, savor an early New Year’s Eve dinner, a river cruise, and more! Start the new year with an intimate and elegant time away with the one you love!
A Holiday Home Away from Home
Finally, for a cozy seasonal retreat, look no further than Brampton 1860, your home base for all sorts of exciting holiday events in Maryland.
Stay in comfy cottages with everything you need, including king and queen beds, wood-burning fireplaces and stoves in most rooms, and luxurious jetted tubs and showers — perfect for staying warm after a long day of outdoor adventures and seasonal activities.
It is an extra special time for us here at Brampton, and we sincerely hope you will book one or more of these exclusive events and celebrate with us!
We wish you and yours a very Merry Christmas, a Happy New Year, and a holiday season filled with joy and laughter.
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