Top 5 Things To Do on the Eastern Shore this Winter

To appreciate the beauty of a snowflake it is necessary to stand out in the cold. ”
—  Aristotle

The trees have finally given up their leaves, and the cold weather is upon us. Still, winter in Chestertown, MD, brings a cozy and tranquil atmosphere for a truly unforgettable getaway. There are so many awesome things to do on the Eastern Shore this winter, making it the perfect place for everyone! Foodies travel here for the oyster season, hunters flock to our shores for waterfowl season, and couples travel here for the ultimate, romantic holiday retreat.

raw oysters - a Maryland Eastern Shore winter treat

1. Eat Fresh, Local, In-Season Oysters

The arrival of winter brings with it the season for fresh oysters! Whether you like them stewed, raw, steamed, fried, roasted, or cooked up into a cake or pot pie, the Eastern Shore certainly does not disappoint. Here are some of our favorite nearby restaurants that know how to serve up some truly delicious oysters:

2. Celebrate the Holidays

‘Tis the season to get in the holiday spirit! There’s so much to do in the area that it can be daunting. Our experienced Innkeepers are here to help you plan the most romantic Christmas getaway with your sweetheart. Spend time together finding the perfect gift on a shopping spree, or perhaps seek some exciting holiday events in and around Chestertown. Winter on the Eastern Shore is one of the most magical times of the year!

3. Go Hunting During Waterfowl Season

With colder weather comes the welcome return of Maryland’s waterfowl season! Seasoned hunters return year after year to the Eastern Shore…which also happens to be the goose-hunting capital of the world!

4. Enjoy Outdoor Winter Adventures

It’s time to enjoy an Eastern Shore winter wonderland! Remember to dress warmly and pack your hats, gloves, boots, long layers, and puffy coats for winter activities during your stay. Here are some of our favorite activities that we can’t wait to share with you:

fireplace and sitting area for a romantic Maryland winter getaway

5.  Cozy up by the Fireplace in Our Beautiful Accommodations

After a long day outside, there’s nothing like returning to a crackling fireplace and comfy room for an evening of relaxation and rejuvenation. Getting cozy at Brampton Inn is one of our favorite Eastern Shore winter activities.

Located in Chestertown, MD, we are conveniently located near some of the best local restaurants and businesses while still being tucked away from the hustle and bustle of city life. There are so many amenities to add to your stay. For example, you can book a private massage in the comfort of your room for a stress-relieving end to a fantastic winter getaway in Maryland. Let Brampton Inn be your home away from home this holiday season.

Enjoy a range of amenities, including:

  • Delicious breakfast served fresh each morning
  • Wood-burning or gas fireplaces are included in most rooms and cottages
  • Cozy accommodations with spa tubs, deep-soaking tubs, infinity baths, or jetted showers
  • Large windows that let in plenty of light for a warm and natural atmosphere
  • King or queen-sized beds with 100% cotton linens

Are you ready to plan a relaxing getaway?

All these and more await at Brampton Inn —  the perfect home base for all kinds of winter activities here on the Eastern Shore. Check availability now.

Published November 2023

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