

Chesapeake Wine Trail
Upper Shore – The upper shore includes Cecil, Kent and Queen Anne's counties, all north of Rt. 50.
Cecil County: Restaurants | Accommodations
Kent County: Restaurants | Accommodations (stay at Crow Farm and Vineyard, Kent County's newest Winery!)
Queen Anne's County: Restaurants | Accommodations
Mid Shore – The mid-shore includes Talbot, Caroline and Dorchester counties.
Dorchester County: Restaurants | Accommodations
Talbot County: Restaurants | Accommodations
Lower Shore – The lower shore includes Wicomico, Somerset and Worcester counties.
Wicomico County: Restaurants | Accommodations
Worcester County: Restaurants | Accommodations

June 25
The Chesapeake Wine Trail Celebrates Summer!
Jun 25, 2011 @ 12

September 24
The Chesapeake Wine Trail Celebrates Harvest & Crush!
Sep 24, 2011 @ 12

Experience the Beauty, the Magic, and the Flavor of the Chesapeake Wine Trail.
Whether you are on your way to the beach or just taking a drive to admire the beautiful Bay, the Chesapeake Wine Trail will lead you through one of the most scenic and charming parts of the state. East of the Chesapeake Bay, Maryland’s Eastern Shore is abundant with seafood, beaches, wildlife and history, and now a beautiful—and delicious—wine trail.
The Eastern Shore is known for its warm days and cool nights. The soil is sandy and well drained, and the climate is moderated by the Chesapeake Bay. This region is growing quickly and it’s no surprise, considering the beautiful waterfront views, rich heritage, abundant wild life and distinctive grape growing environment.
When you come to the Eastern Shore to visit our wineries, you will be charmed by the boutique atmosphere, intimate settings and the attention to detail and quality. Stroll along the bay or take a trip to the past while visiting some historical sights…all while enjoying some of Maryland’s best wine along the Chesapeake Wine Trail.
Activities
About the Winery
Crow Vineyard & Winery Tasting Room will be opened June 22, 2012. We also have a farmstay B&B, make it a weekend event
Activities
About the Winery
Whether you’re enjoying a quiet evening or celebrating special times, Great Shoals has a place in your glass. Our hand crafted sparkling wines will mark any occasion with tiny bubbles.
We blend fruit from regional sources to create brut sparkling wines using the traditional méthode champenoise. Each bottle of Great Shoals Sparkling is filled with distinctive and complex flavors melded by the champagne process.
Operations of Great Shoals Winery are based in Mount Vernon, Somerset County, MD, along a sandy bank of the Wicomico River, not far from Great Shoals Light on the Upper Tangier Sound of the Chesapeake Bay.
Hours
Please visit the Maryland Wine Bar at Berlin to taste all of our wines. The address is 103 N Main St, Berlin, MD 21811. (410) 629-1022. Hours: Monday - Saturday 1 to 10PM. Tours of the winery are by appointment only. Please call in advance.
Address and Contact
26431 Mason Webster Rd
Princess Anne, MD 21853
(410) 849-9616
Activities
About the Winery
Vineyard owner and winemaker Thomas R. Shelton has been growing grapes since 1999 on his Eden, MD property which borders the pristine Wicomico Creek. It is the first licensed vineyard in Wicomico County. The name Bordeleau - “edge of the water” - was chosen to reflect not only the distinctive environment where our grapes are hand-harvested, but also the favorable climate similarities to the Bordeaux region of France. Currently, 10 different varieties of grapes are under cultivation on 10+ acres.
Activities
About the Winery
Mark Cascia Vineyards grows 12 acres of premium wine varietals on Kent Island on Maryland's Eastern Shore. Cascia Vineyards is a unique family run waterfront winery located on Kent Island, overlooking the waters of the Chesapeake Bay. We produce hand-crafted premium red and white wines, as well as dessert wines, from vinifera and native varietals, grown in our vineyard. Our waterfront winery and event facility provide an extraordinary opportunity to experience the best that Queen Anne’s County has to offer.
Activities
About the Winery
Cassinelli Winery & Vineyards is a family-owned and operated boutique winery located on the Eastern Shore of Maryland. Our goal is to produce great wines from our own fruit and fruit sourced from other eastern shore Vineyards. Our 110-acre farm is planted with Merlot, Chardonnay, Viognier, Malbec, Petit Verdot and San Giovese vines. In addition to walking in the vineyards, you can enjoy visiting our 25 Black Angus cows, two buffalo and two donkeys. In the fall we have a 3-acre pumpkin patch and apple orchard. Our twelve wines include Merlot, Barbera, Chardonnay, Vidal, Pole Dancer Sweet, Rosé and Chocolate Kiss. Tasting is $6 and you keep our etched glass.
Activities
About the Winery
Costa Ventosa is a casual, fun winery located on 10 acres of vineyards and farmland in beautiful Worchester County, just 10 minutes from Ocean City. In Italian, “Costa Ventosa” means “Windy Coast.” Our tasting room has a distinct Shore cottage feeling. Take a tour of the wine production area, gaze out over our 4-acre vineyard, or sit on the front porch with a glass of our yummy wines.
Activities
About the Winery
Dove Valley grapes are grown by the head of the Chesapeake Bay, The area has just the right soil, sun, and air flow to produce premium grapes. Our award-winning wines are hand crafted from start to finish. Dove Valley Winery hosts many exciting events throughout the year.
Activities
About the Winery
After four generations of farming in the Salem area of Dorchester County as Lazy Day Farms, the Layton family has decided to share their love of agriculture by expanding their crops with wine grapes and by making wine. Come take pleasure in a "Lazy Day" at Layton's Chance Vineyard and Winery by walking the nature trails, relaxing in the picnic areas, touring our farm and vineyard, all the while drinking our great wine. Layton's Chance has produced five wines in its inaugural year, with a pleasing option for everyone. We offer reds and whites, sweet and dry, and our house Rosé, made with 100% Layton's Chance chambourcin grapes. We offer tours of the farm, vineyard, and winery, and our winery event room is an ideal location for hosting private events.
Activities
About the Winery
The first licensed winery on the Eastern Shore of Maryland, Little Ashby Vineyards is located on the banks of the Miles River in historic Talbot County, near the quaint colonial towns of Easton and St. Michaels. The winery can be reached by boat as well as by car or bicycle. Its elevated riverbank position gives the vineyards their own distinct microclimate, cooled by river breezes on hot summer nights and moderated by the warmer water temperature during the winter. Dogs are welcome.
Activities
About the Winery
St. Michaels is the largest winery on Maryland's scenic Eastern Shore. We are open seven days a week to greet visitors and pour our hand-crafted wines. Our winery is located in the Historic Old Mill complex, also home to artists, a floral designer, and other unique shops. We feature a broad spectrum of award-winning wines to satisfy any tastes. Our spacious production room is perfect for group events.
Activities
About the Winery
Terrapin Station Winery is dedicated to combining old world standards with new and innovative technology to make the best wine possible from grapes best suited to our location. Our focus is making everything about wine fun and approachable, not stodgy and serious. And by contributing a portion of our sales to research and preservation of the Diamondback Terrapin, we hope to extend the legacy of the Bay, the Terrapin and the small farm for future generations.
Activities
About the Winery
Located 3/4 miles north of Sudlersville on Maryland’s Eastern Shore, Tilmon’s Island Winery is a boutique winery, producing Cabernet Franc, Merlot, Chambourcin, Chardonnay, and Pinot Grigio grapes purchased from local vineyards in Queen Anne’s and Caroline Counties.



















