The Chesapeake Wine Trail is Maryland's Eastern Shore wine trail — more than a dozen wineries spread across the Atlantic Coastal Plain from Kent Island south through Easton, St. Michaels, and down to the coast near Berlin and Ocean City. The trail connects waterfront vineyards, working farms, and small-town tasting rooms in a region defined by Bay views, local seafood, and a slower pace than the Western Shore. This guide covers the wineries on the Chesapeake Wine Trail, how to plan a day trip by cluster, and how to get your group there from Baltimore, Annapolis, or DC without a designated driver.
- Trail location: Maryland's Eastern Shore — Cecil, Kent, Queen Anne's, Talbot, Dorchester, and Worcester Counties, spanning roughly 120 miles from the upper Bay to the Atlantic coast.
- Signature wines: Barbera, Chambourcin, Vidal Blanc, and Catawba thrive in the coastal plain's sandy soils and maritime climate. Winemakers craft wines specifically to pair with Chesapeake Bay seafood.
- Day trip pacing: Three to four wineries per day, targeting one geographic cluster. The trail is too spread out to cover in a single visit.
- Closest crossing: Kent Island wineries are just 20 minutes from Annapolis across the Bay Bridge — the fastest entry point to the Chesapeake Wine Trail from the Western Shore.
- No public transit: Wineries sit on rural Eastern Shore roads. A chauffeured group vehicle handles Bay Bridge traffic and country-road navigation so everyone can participate in tastings.
Chesapeake Wine Trail
Cecil to Worcester County
Across the Bay Bridge
Visit in One Day
What Is the Chesapeake Wine Trail?
The Chesapeake Wine Trail is one of Maryland's eight designated wine trails, organized by the Maryland Wineries Association. It connects wineries on the Eastern Shore and upper Chesapeake Bay — from Cecil County at the head of the Bay through Kent, Queen Anne's, and Talbot Counties, down to Dorchester and Worcester Counties near the Atlantic coast. The trail's identity is built around the Chesapeake Bay itself, the seafood culture that defines the Eastern Shore, and the Atlantic Coastal Plain terroir that produces wines crafted to complement that food. If you have explored the Piedmont Wine Trail north of Baltimore, the Chesapeake trail offers a completely different landscape, climate, and wine profile on the opposite side of the Bay.
Wineries on the Chesapeake Wine Trail
The Chesapeake Wine Trail's official listing includes more than a dozen wineries. Here are the major stops organized by area.
Upper Bay — Cecil County
Blue Elk Vineyard (Bohemia Overlook) — grapes grow along a hillside beside the Elk River, with a 1930s barn serving as the tasting room. Bohemia Manor Farm (Chesapeake City area) — a Tuscan-style chateau with Chesapeake water views and a popular wedding venue alongside the winery. Dove Valley Vineyard & Winery (Rising Sun) — a rustic tasting room known for vineyard-view sunsets and Dove Valley Gold.
Kent County and Kent Island
Crow Vineyard & Winery (Kennedyville) — a 365-acre working farm with grass-fed Angus beef, a farmstay B&B in a renovated 1847 farmhouse, and a Barbera Reserve considered one of the leading wines in Maryland. Cascia Vineyards & Winery (Stevensville, Kent Island) — a waterfront estate on Cox Creek with 12 acres of premium varietals, including rare native grapes. Kent Island's position at the Bay Bridge makes Cascia the most accessible Chesapeake Wine Trail winery from the Western Shore. Love Point Vineyards & Winery (Kent Island) — a waterfront tasting room overlooking the Chester River.
Talbot County and Mid-Shore
St. Michaels Winery — 18 varietals in the Historic Old Mill District of one of the Eastern Shore's most visited waterfront towns. Far Eastern Shore Winery (Easton) — a modern downtown tasting room with East Asian-influenced flavor profiles. Triple Creek Winery (Wye Mills area) — a family-run farm winery operated by four brothers, known for their Island Pickin' tropical sangria.
Lower Shore — Dorchester and Worcester Counties
Bordeleau Vineyards & Winery (Eden) — a water's-edge estate with a signature outdoor fireplace patio and Chambourcin Lot 6, a full-bodied red built to pair with Chesapeake shellfish. Layton's Chance Vineyard & Winery (Vienna) — 14 acres of vineyards with a nature trail and their Freedom blend named in honor of Harriet Tubman. Windmill Creek Vineyard & Winery (Berlin) — a vineyard, wildflower farm, and event venue three miles from downtown Berlin and a short drive from Ocean City.
Chesapeake Wine Trail Wineries at a Glance
Here is how the wineries compare by location and cluster.
| Winery | Town / Area | Cluster |
|---|---|---|
| Blue Elk Vineyard | Bohemia Overlook | Upper Bay |
| Bohemia Manor Farm | Chesapeake City | Upper Bay |
| Dove Valley Vineyard | Rising Sun | Upper Bay |
| Crow Vineyard & Winery | Kennedyville | Kent County |
| Cascia Vineyards | Stevensville (Kent Island) | Kent Island |
| Love Point Vineyards | Kent Island | Kent Island |
| St. Michaels Winery | St. Michaels | Mid-Shore |
| Far Eastern Shore Winery | Easton | Mid-Shore |
| Triple Creek Winery | Wye Mills | Mid-Shore |
| Bordeleau Vineyards | Eden | Lower Shore |
| Layton's Chance | Vienna | Lower Shore |
| Windmill Creek | Berlin | Lower Shore |
Planning a Chesapeake Wine Trail Day Trip
Three to four wineries is realistic in one day, with 45 minutes to an hour at each stop plus drive time. The trail covers a large region, so a focused day trip should target one cluster rather than attempting the full 120-mile span.
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Kent Island + Mid-Shore (best for Annapolis and Baltimore visitors). Cascia Vineyards → Love Point Vineyards → St. Michaels Winery → Far Eastern Shore Winery in Easton. Short drives between stops, visitor-friendly towns, and a crab house lunch in St. Michaels.
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Upper Bay (best for Baltimore and Wilmington visitors). Blue Elk Vineyard → Bohemia Manor Farm → Crow Vineyard & Winery. A tight geographic cluster with farmstead and waterfront atmospheres near Chestertown.
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Lower Shore + Beach (best combined with an Ocean City weekend). Windmill Creek → Bordeleau → Layton's Chance. Pair winery stops with a beach trip for a full weekend getaway.
Wine Tour Transportation for Groups
The Chesapeake Wine Trail's geography makes group transportation practical for any party of six or more. Wineries are on rural Eastern Shore roads with no public transit, limited cell service in spots, and 15- to 30-minute drives between stops. A designated driver is not just inconvenient — it is a wasted seat at every tasting room.
A chauffeured vehicle handles Bay Bridge traffic and Eastern Shore navigation while everyone participates fully. The driver picks up the group in Baltimore, Annapolis, or the DC area, crosses the Bay Bridge, visits 3 to 4 wineries on a prearranged route with an optional lunch stop at a crab house, and returns the group after the day's tastings. Wine purchases ride in the vehicle's storage. Bayside Limousines has coordinated wine tour transportation across Maryland's trails for over 33 years — if you are exploring other Maryland wine regions, the Legacy Wine Trail in Prince George's and Charles Counties is another strong option close to DC.
| Coming from Annapolis | Kent Island + Mid-Shore cluster — 20 minutes to Cascia, then St. Michaels and Easton for a waterfront wine-and-seafood day. |
| Coming from Baltimore | Upper Bay cluster via I-95 (skip the Bay Bridge) or Kent Island via I-97. Both put you at tasting rooms in under 75 minutes. |
| Combining with a beach trip | Lower Shore cluster — Windmill Creek near Berlin, Bordeleau, and Layton's Chance, then continue to Ocean City for the weekend. |
| Ready to book? | Call (410) 451-0000 — Bayside matches the vehicle and route to your group's size, cluster preference, and schedule. |
Eastern Shore Wine Tour Without the Designated Driver
Bayside Limousines has been running wine tour and group transportation across Maryland for over 33 years — owned fleet, W-2 chauffeurs, and fixed-rate pricing. Cross the Bay Bridge, taste the Chesapeake Wine Trail, and let the driver handle the rest.
Frequently Asked Questions
Winery listings, trail membership, and drive times verified via the Maryland Wineries Association and Visit Maryland. Check individual winery websites for current hours and reservation requirements.