Chesapeake Wine Trail
From the mountains in the west, to the Atlantic in the east, Maryland is blessed with a little bit of everything, but the one thing that we’ve got that you can’t find anywhere else is the heart of the Chesapeake Bay. A world treasure known for its panoramic vistas, startling varieties of wildlife, incredibly lush farmlands, and the world’s greatest seafood, it’s also home to more than a dozen fantastic wineries on the Chesapeake Wine Trail.
The Chesapeake Wine Trail is a must-do Eastern Shore escape where handcrafted wines are thoughtfully grown to complement Maryland’s legendary seafood, stunning waterfront views, and warm hospitality. Journey through the region’s wide-open landscapes, unwind at an easy pace, and savor distinctive varietals like Barbera that have helped put the Atlantic Coastal Plain on the wine map.
Between tastings, discover the Eastern Shore’s rich heritage and culture—from stories of Harriet Tubman and Frederick Douglass to skipjack sails on the Chesapeake Bay. Explore creative traditions at the Fiber Arts Center of the Eastern Shore, ride the historic Oxford Bellevue Ferry, and plan a visit during Salisbury’s Maryland Folk Festival. Wherever your travels take you, each stop along the Chesapeake Wine Trail offers memorable flavors and authentic Eastern Shore charm.
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Blue Elk Vineyard
Located in the center of Bohemia Overlook, grapes grow along the hillside beside the shore of the Elk River. Blue Elk's terroir produces grapes unique to the area. A 1930's barn serves as a tasting room.
Bohemia Manor Farm
With its Tuscan-style chateau and stunning water views, it’s no wonder Bohemia Manor Farm is a favorite for weddings and other occasions. But their philosophy of sourcing, growing, and managing the best fruit anywhere is what truly sets them apart.
Bordeleau Vineyards & Winery
Centered on a beautiful brick manor, this water’s-edge winery is simply a slice of heaven. A particular favorite is the brick patio centered on a massive fireplace, perfect for toasting an unforgettable evening. Don’t miss out on Chambourcin Lot 6 - Bordeleau’s signature red is full-bodied with aromas of chocolate, toasted wood, mulberries, herbs and pralines over a tangy sandalwood and sour cherry finish.
Broken Spoke Vineyard & Winery
This Eastern Shore treasure is beloved for its adorable, wandering sheep, but don’t let that let you miss their remarkable wines. Broken Spoke’s Vidal Blanc brought home double Gold at the 2017 Maryland Comptroller’s Cup Wine Competition.
Casa Carmen Wines
Casa Carmen is a boutique family winery that produces artisanal crafted Old World-style wines of uncompromising quality.
Cascia Vineyards
Nestled on the bank of Cox Creek on Kent Island, Cascia Vineyards is home to 12 splendid acres dedicated to growing premium varietals. Their hand-crafted reds and whites are simply wonderful, but their premium dessert wines, some made from rare, native grapes grown onsite, are a unique treat you won’t want to miss.
Crow Vineyard & Winery
At its roots, Crow Vineyard & Winery wants its guests to experience their wines. That’s why they encourage visitors to get out in their arbors and pick grapes and spend a night in their Farmstay B&B, to better understand the love that goes into every bottle. It makes a communal feast with a glass of their brilliant Barbera Reserve all the more unforgettable, and is why Al Spoler of “Cellar Notes” has called Crow, “One of the leading lights in Maryland Wine.”
Dove Valley Vineyard & Winery
From their rustic tasting room to the spectacular sunsets over their lush fields, Dove Valley Vineyard is just a place that makes you want to stay awhile. It doesn’t hurt that Dove Valley is home to such spectacular wines as their splendid Dove Valley Gold, named after the owner’s beloved retriever Goldie.
Far Eastern Shore Winery
Hip and modern with flavors of East Asia, Far Eastern Shore Winery is a unique destination winery located in the heart of Easton.
Layton’s Chance Vineyard & Winery
More than 14 acres of vineyards, an inviting picnic area, outdoor games, a nature trail, and welcoming staff make Layton’s a great stop on any wine tour. Try Freedom, a seminal blend of native Catawba and Chambourcin grapes inspired by Harriet Tubman.
Love Point Vineyards and Winery
Located on Marylands Eastern shore on Kent Island. This winery offers a beautiful waterfront tasting room with expansive views of the Chester river. We have a laid back coastal vibe offering award winning wines. There's love in every bottle!
St. Michaels Winery
Located in the heart of beautiful St. Michaels in the Historic Old Mill District, an afternoon at the winery is the perfect capstone to a trip to the Shore. Stop in for a glass, walk around for some shopping, then stroll back for another round.
Windmill Creek Vineyard & Winery
The vineyard is a family owned and operated vineyard, winery, wild flower farm, and events venue located three miles from downtown Berlin, Maryland on the grounds of the Historic Mariner House.
Trip Tips
The Chesapeake Wine Trail makes a great way to reach the beach! Break up your trip to Ocean City or Assateague with stops along the Chesapeake Wine Trail, get to know more of Maryland, and make the journey as much fun as the destination.
Annapolis is the sailing capital of the world, home of the U.S. Naval Academy, and one of the most beautiful cities in the world. Make a stop to walk the bricked streets of Annapolis, and tour Ego Alley, show off spot for some of the most amazing yachts anywhere.
