Some of the Best Wineries on the Eastern Shore of Maryland

Here at the Brampton Inn, we are excited to be just minutes away from some of the Eastern Shore’s best wineries (and distilleries)! Whether you’re looking to taste some unique, local varietals or simply enjoy the stunning surroundings with a group of friends/family, wineries on the Eastern Shore of Maryland can’t be missed. Keep reading to learn more about the local wine scene. For more local insight, be sure to check out our free Guide to the Eastern Shore of Maryland!

Our Favorite Places and Spaces


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“Stay and Sip” With Our Crow Winery Tour Package!

Available Sunday through Thursday

Discover Crow Vineyard and Winery, a 3rd-generation working farm. In 2008, the Crow family planted their first grapes and started an artisan wine-making operation. They offer special events such as festivals, pizza nights, grill nights, wine-and-chocolate pairings, mystery dinner theater shows, wine dinners, and wine seminars. Allow the friendly staff at Brampton Inn to book your tour so you don’t have to lift a finger! Call 410-778-1860 or book online!

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About Crow Vineyard and Winery

This 365-acre farm was named after first generation farmer Roy Crow. Here, you’ll discover 12½ acres of vines and about 100 head of grass-fed Black Angus cattle. The Eastern Shore is one of Maryland’s fastest growing wine regions. This beautiful land borders the magnificent Chesapeake Bay, an estuary that brings together fresh and salt water. The surrounding soil is sandy and well-drained, and the climate produces warm days and cool nights perfect for grape growing. As part of the “Rivers to Canal Wine Corridor,” Crow Vineyard is proud of their artisan wine-making. For several years, they have earned the Maryland Governor’s Cup Medal status and gold status at international competitions. We are happy to support this neighboring winery!

Other Nearby Wineries and Distilleries

Casa Carmen Boutique Maryland Winery

Just five miles away from Brampton Inn, you’ll find Casa Carmen Boutique Winery (just a 5-minute drive from the heart of downtown Chestertown)! This absolutely gorgeous vineyard focuses on dry wines, so Sauvignon Blanc and Pinot Grigio fans will feel right at home here. Casa Carmen is located along the Chesapeake Wine Trail, which positions them just 90 minutes from D.C., Baltimore, and Philadelphia. The owners, two siblings from Ecuador, bring their experience with and passion for global wines to the shores of the Chesapeake.

Bad Alfred’s Distilling

If you’re not quite a wine person but still want a buzz when you’re in town, check out Bad Alfred’s Distilling! This spot is part micro-distillery and part wood-fire grill, so you’re good to go if hunger strikes. Bad Alfred’s is located in Chestertown, Maryland, just 1½ miles away from Brampton Inn! You’ll love Bad Alfred’s handcrafted brandy, gin, craft brews, and, of course, wood-fired pizzas.

Fine Wines and Good Company Await at Brampton Inn!Crow Winery red wine with steak

Whether you’re here exploring wineries on the Eastern Shore of Maryland, checking out some local seafood restaurants, or sampling the many fun things to do in the Chesapeake Bay area, Brampton Inn is the best place to stay in the area! You’ll love getting a good night’s sleep in one of our bright, airy, and spacious accommodations and wake up to a freshly prepared breakfast you’ll never forget. Later, join us for tea time and social hour for light snacks and drinks (yes, we offer fine wines, too)! Finally, end your day “porch surfing” as the sun sets over the horizon. By the end of your first day staying with us, you’ll see why so many people discover their most relaxed (and well-fed) selves here!

Ready for a true taste of Maryland’s Eastern Shore? Book your stay at Brampton Inn! We can’t wait to welcome you to beautiful Chestertown.