Everything You Need to Know About Holiday Happenings in Chestertown, Maryland

If there’s one persistent truth about the holiday season, it’s that it flies by at warp speed. The same is true of the holiday happenings in Chestertown, Maryland. Though the season comes and goes quickly, that’s all the more reason to enjoy it! Below, we’ve compiled all of the best ways to spend time this holiday season here in Chestertown, Maryland. You can also enjoy an early Christmas present from Brampton Inn when you unwrap your free Travel Guide to the Eastern Shore of Maryland! It features our favorite events, restaurants, and attractions happening this holiday season.

Some of the Best Holiday Happenings in Chestertown, Maryland

Thanksgiving Dinner at Osprey Point

An Eastern Shore Thanksgiving is the perfect way to spend quality time with loved ones this fall! If an elegant and special holiday dinner is what you seek, the waterfront restaurant at Osprey Point is a good place to host your afternoon festivities. Located in Rock Hall (12 miles southwest of Brampton Inn), this restaurant near Chestertown serves a turkey-centric meal supplemented by plenty of sides.

Holiday High Tea at Brampton Inn

There are so many reasons why the holiday season is a special time here at Brampton Inn. During this time of year, our fireplaces are roaring, the inn is decorated for Christmas, and our annual traditions are in full swing. One of our favorite holiday rituals is the High Tea! This festive and lighthearted celebration is the perfect way to kick off winter in Chestertown.

If you like our usual Tea Time and Social Hour, you will love our High Tea celebration! The menu normally consists of dishes like Pumpkin Bisque followed by open-faced turkey, roast beef sandwiches, and piping hot chicken pot pie. There will also be pots of freshly prepared tea available. Dessert is involved, too! Expect some sweet goodies like traditional English trifle or chocolate cakes, scones, and/or lemon curd. It’s really is quite a feast! The most incredible part? There is no extra charge to you, our beloved guest! If you wish to join us for some holiday fun, it’s included in the room rate. Consider it an early Christmas present from Brampton Inn to you!

Other Fantastic Holiday Events in Chestertown

  • A Dickens of a Christmas
  • Festive First Friday with complimentary food and drink
  • Live Music and caroling in downtown Chestertown
  • Food booths with Victorian fare
  • Street theater (scenes from A Christmas Carol and Oliver)
  • Historic Holiday House Tours
  • Carriage rides
  • Bonfires
  • Antique bicycle demonstrations by “The Wheelmen”
  • Shopping specials on Black Friday
  • Chestertown Farmers Market
  • Oyster roasts.

Stay Off the Beaten Path But Near All of the Action This Year!View of bathtub in Mulberry Cottage Brampton Inn near the best Holiday Happenings in Chestertown, Maryland

Whether you’re searching for a new way to spend the holiday season or to continue an existing tradition, Brampton Inn is your family’s perfect home-away-from-home. The Eastern Shore of Maryland isn’t called “The Land of Pleasant Living” for nothing! Our area is characterized by beautiful country roads, plenty of rich history, delicious coastal cuisine, and cozy cottages. The holidays here make the atmosphere even more magical! No matter which of these events you choose to attend, you’ll love relaxing in your bright, airy, and spacious room at Brampton Inn. The holidays are the best time to experience our gorgeous grounds and premium amenities!

Ready to start planning an unforgettable holiday stay with us? Check our availability now! We can’t wait to welcome you.