Holiday Events In and Around Chestertown Maryland

The holiday season truly is the most wonderful time of the year, from the magic of falling snow to fun festivities with friends and family. Experience all the holiday events in Maryland with a getaway at our romantic Chestertown Inn. Enjoy good food with great friends and learn more about the celebrations in and around Chestertown, MD.

Thanksgiving at Brampton Bed and Breakfast

A Brampton Thanksgiving Getaway

Indulge in an authentic New England Thanksgiving with our Ultimate Eastern Shore Thanksgiving Getaway package from November 22–26, 2023. 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.

a woman at a holiday event in Maryland

Dickens of a Christmas

Secondly, join us this year for the annual Dickens of a Christmas and participate in downtown holiday festivities. There’s so much to do and see! 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!

homemade wreaths being sold at a holiday event in Chesterfield, MD

Yuletide Festival and Holiday Marketplace

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 chuck-full with 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 really aren’t so different. Reserve tickets now for this not-to-miss event of the season!

guests attending a wreath making class in Maryland

Festive Wreath-Making Class

Create your own yuletide decor and have something special to take home after our special holiday wreath-making classes at Brampton! Spend an afternoon with us filled with friends and fun! We have three wreath-making classes scheduled, all from 2-4pm:

  • October 22, 2023 — Halloween-themed
  • November 12, 2023 — Fall-themed
  • December 10, 2023 — Holiday-themed

During the holidays, a wreath is a great centerpiece for your front door or anywhere else in your house. It adds the perfect touch of festivity to any space — plus, you can hang it proudly, knowing you made it yourself!

a table set for Christmas dinner at Brampton Bed and Breakfast Inn

Christmas Dinner at Brampton

The premier event of the season, and certainly one of our favorites, Christmas dinner at Brampton Inn 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 true reason for the season together. Learn more about the details of our Home for the Holidays package.

Ring in the New Year at Brampton

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 2024 with an intimate and elegant time away with the one you love!

The Sunrise Room in the Garden Cottage at Brampton Inn showing the king-sized bed, sitting area with leather-covered furniture, and a fire in the fireplace.

A Holiday Home Away from Home

Finally, for a cozy seasonal retreat, look no further than Brampton Inn, your home base for all sorts of exciting holiday events in Chestertown, 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.


Updated October 2023

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Dine in Style! 

If you are looking for a unique dining experience, we have two amazing dining-series this season!

Check out Dining Under the Stars with Chef Kurt Peter starting May 2!


Gourmet Diner Club with chef Jordan Lloyd starting May 23!

Dining and entertainment experiences to remember! See our Specials page.

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