Updated Dec 2024. Trade those winter blues for romantic hues by exploring the best weekend trips from Baltimore in winter. Maryland’s Eastern Shore is the perfect setting for a convenient and romantic winter weekend getaway. Just a short drive from Baltimore, Chestertown is the perfect place for couples to escape the hustle and bustle, stroll hand-in-hand through its historic streets, and cozy up by a fire at Brampton 1860.
Add some warmth to your winter with a proposal or romantic escape. See for yourself why the Eastern Shore of Maryland makes for a wonderful Baltimore weekend getaway!
How Far Is it From Baltimore to Chestertown, MD?
Chestertown is one of the most convenient romantic places to visit near Baltimore, around 1 1/2 hours away. The easiest and most scenic way to get to Chestertown is by going South across the Chesapeake Bay Bridge. You can also drive around the bay via I-95 North and MD 213 South. This northern route via Elkton just adds 20 minutes to your trip and also offers charming views.
Things to Do in Chestertown in Winter
Are you ready to experience one of the best places to visit in Maryland for couples? Chestertown has no shortage of winter activities for you to enjoy.
1. See the Tundra Swans
Each winter, flocks of majestic tundra swans gather along the Eastern Shore of Maryland, creating a breathtakingly romantic scene. The swans typically begin to arrive in mid-November and depart in March. Nature lovers can get an up-close look at these beautiful creatures in their natural habitat at the Eastern Neck Wildlife Refuge. Make sure to bring your camera! You may also spot bald eagles, Canada Geese, ducks, mallards, foxes, deer, groundhogs, and wild turkey.
2. Explore Chestertown
With fabulous dining, fascinating historic sites, and a thriving arts scene, Chestertown has so much to offer year-round. Fewer crowds during this time of year give you the best browsing experience for local shops, galleries, and museums. Take a stroll around Washington College, explore the exhibits at Massoni Art, or enjoy delicious cuisine at one of Chestertown’s local restaurants. And if you’re visiting in December, don’t miss Dickens of a Christmas! Held downtown, this annual themed event includes festive carriage rides, fire dancers, entertainment, street theatre, a 5K race, and so much more. There’s no better way to kick off the holiday season!
3. Take a Hike in the Cool, Crisp Air
Here on the Eastern Shore, we don’t get tons of snow. However, we do love it when fresh snow lightly blankets the ground. It transforms the land into our own winter wonderland just waiting to be explored. One of the best things about winter is the fresh, crisp, and cool air. It’s a great time to grab your hiking boots and head outdoors to wander through our wintry landscapes. Afterward, come home to Brampton 1860 and warm up with a cup of hot tea!
4. Sample Winter Wines
If you’re looking for something romantic to do with your sweetheart, why not enjoy a tasting at Crow Vineyard and Winery? Just minutes from Brampton 1860, the winery features a wide array of award-winning selections. In fact, their wines have achieved gold status at international competitions for four years in a row! Come sample some for yourself in their tasting room, open daily from noon until 5 p.m. From Sparkling Vidal to compelling red blends, there is something for every wine-lover here!
5. New Year’s Eve Romance Packages
Planning a proposal? Looking to begin the next year with romance? Start the new year off right by celebrating at Brampton 1860 this winter. Our Cheers to New Years! and “I Do” Proposal specials include everything you could possibly want for a romantic winter Baltimore weekend getaway.
We include all the special touches to make your romantic vacation unforgettable. Imagine you and your loved one ringing in the new year aboard a historic 1940s-themed cruise with live music or celebrating your engagement in the perfect setting.
Enjoy a Relaxing Winter Break at Brampton 1860
Wouldn’t you like to experience one of the best weekend trips from Baltimore in winter? Winter is one of the quieter seasons along the Eastern Shore of Maryland, with fewer crowds and lower rates. This is an ideal time to book your romantic stay at Brampton 1860! Our well-appointed rooms and cottages feature top-notch amenities to ensure that your stay is a relaxing one, letting you and your loved one focus on each other. Plus, our accommodations feature a fireplace to keep you warm and cozy during the colder months.
With plenty of space and privacy, Marley’s Cottage would be a wonderful choice for your Eastern Shore of Maryland getaway. Enjoy comfortable furnishings, gorgeous treetop views, and complimentary breakfast each morning.
Check our availability and book your stay today. We can’t wait to welcome you!
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