5 Eastern Shore Winter Activities That Will Make You Want to Visit Right Now

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

—  Aristotle

Winter in Chestertown, MD, ushers in leafless landscapes, frozen bodies of water, snow, and a quiet air of peace and tranquility. That being said, there are so many wonderful winter activities on the Eastern Shore that make it the perfect place for a getaway. Foodies travel here for oyster season. Hunters flock to our shores for waterfowl season. Even young couples find themselves in town to celebrate a romantic holiday retreat. 

Read on for some of our favorite suggestions on what to do this time of year. Then, get your free copy of our Vacation Guide for even more thoughtful local insight! 

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5 of Our Favorite Eastern Shore Winter Activities 

1. Eat Fresh, Local, In-Season Oysters

Winter’s arrival brings with it an ocean full of fresh, in-season oysters! Maybe you’d like to attend a local oyster roast. Perhaps you’re looking for the best restaurant in town that serves up these tasty morsels. Whether you like them stewed, raw, steamed, fried, roasted, or cooked up into a cake or potpie, the Eastern Shore does not disappoint. Here are some of our favorite nearby restaurants that know how to serve up a delicious oyster dish: 

  • The Harrison House on Tilghman Island
  • Chesapeake Landing near St. Michaels
  • Harris Crabhouse and Seafood Restaurant in Grasonville
  • Bay Wolf in Rock Hall

2. Celebrate the Holidays 

‘Tis the season to get in the holiday spirit! Plan a romantic Christmas getaway with your sweetheart. Plan a shopping trip with your sisters. Or seek out exciting annual festivities to enjoy with your friends and family. 

3. Go Hunting During Waterfowl Season 

Colder weather welcomes the return of Maryland’s waterfowl season! Seasoned hunters return year after year to the Eastern Shore which also happens to be the goose hunting capitol of the world. 

4. Enjoy Outdoor Winter Adventures 

Bring your snow boots and some long layers and embark on an outdoor winter adventure during your stay on the Eastern Shore! Some of our favorite activities include: 

  • Visit the Adkins Arboretum in Tuckahoe State Park
  • For those who would rather birdwatch then hunt, check out the Eastern Neck National Wildlife Refuge which serves as a feeding ground for many local species including tundra swans 
  •  Go snowshoeing or cross country skiing 

5.  Cozy up by the Fireplace in Our Beautiful Accommodations

brampton christmasGetting cozy at Brampton Inn is definitely 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. Enjoy a range of amenities including: 

  • Delicious breakfast each morning
  • Wood-burning or gas fireplaces in most rooms and cottages
  • Accommodations with spa tubs, deep-soaking tubs, infinity baths, or jetted showers
  • Large windows for ample natural light
  • King or queen-sized beds with 100% cotton linens
  • & more

Are you ready to plan a relaxing getaway? Check our availability and book your stay today. 

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