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.
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.
Restaurants & Accommodations
The tourism offices throughout the Chesapeake Wine Trail host information about restaurants and accommodations.
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
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
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
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
Trail Sponsors
Along The Trail
Wineries on the Trail
Bordeleau Vineyards and Winery
Activities:
Hours:
Wed-Sat 12-6pm, Sun 12:30-6pm
Wed-Sat 12-6pm, Sun 12:30-6pm
Cascia Vineyards
Activities:
Location:
1200 Thompson Creek Road
Stevensville, MD 21666
410-604-2127
1200 Thompson Creek Road
Stevensville, MD 21666
410-604-2127
Hours:
Not currently open to the public.
Not currently open to the public.
Cassinelli Vineyards and Winery
Activities:
Hours:
Sat & Sun 12-5 pm
Sat & Sun 12-5 pm
Costa Ventosa Winery and Vineyard
Activities:
Hours:
Friday-Sunday 12-6 During the week by chance or appointment
Friday-Sunday 12-6 During the week by chance or appointment
Dove Valley Winery
Activities:
Hours:
Thursday-Monday 11am-7pm
Thursday-Monday 11am-7pm
Great Shoals Winery
Activities:
Hours:
Contact us for tours, tasting, and sales. Our tasting room is yet to have regular hours, but we'd love to hear from you. (410) 849-9616 or Info@Greatshoals.com
Contact us for tours, tasting, and sales. Our tasting room is yet to have regular hours, but we'd love to hear from you. (410) 849-9616 or Info@Greatshoals.com
Layton's Chance Vineyard and Winery
Activities:
Hours:
11am-5pm Monday-Thursday 11am-6pm Friday & Saturday 12pm-5pm Sunday
11am-5pm Monday-Thursday 11am-6pm Friday & Saturday 12pm-5pm Sunday
Little Ashby Vineyards
Activities:
Hours:
July —Wed - Sun. Other times by appointment only.
July —Wed - Sun. Other times by appointment only.
St. Michaels Winery
Activities:
Hours:
Mon - Fri 12-6pm, Sat 12-7pm, Sun 12-4pm
Mon - Fri 12-6pm, Sat 12-7pm, Sun 12-4pm
Terrapin Station Winery
Activities:
Hours:
April-October Hours Saturday-Sunday 12-6 See our website for additional hours and special events
April-October Hours Saturday-Sunday 12-6 See our website for additional hours and special events
Tilmon's Island Winery
Activities:
Hours:
Sat 12 - 5 p.m.
Sat 12 - 5 p.m.
Wine Trail Events
No Wine Trails Events Exist.
