Rivers to Canal Wine Corridor | Maryland | USA / by Brian Yost


The Eastern Shore of Maryland is one of the state’s four primary wine regions. Despite the single regional designation, the northern and southern ends are very different places. Drivers crossing the Chesapeake Bay Bridge from Annapolis must make a distinct choice. The road south is clogged with beach traffic headed toward Ocean City as are the roads east to Rehoboth and the ferry to Cape May, New Jersey. Northern routes, on the other hand, extend into a region recently designated the Rivers to Canal Wine Corridor.

The Rivers to Canal section of the “Shore” is bordered by Delaware in the east and the Chesapeake Bay defines its jagged western boundary. Driving north, one will cross the Chester, Sassafras and Bohemia Rivers before reaching the C&D Canal--the four waterways from which the region’s name is derived. Many travelers are unaware that they are passing through one of the east coast’s premier wine tourism destinations.

Chesapeake City

Chesapeake City

Maritime Communities

There are no major urban areas in the northern reaches of the Eastern Shore. The local economy was traditionally fueled by agriculture and the Chesapeake Bay. Today, tourism is an economic driver; so the numerous small, maritime communities all offer something for visitors. Two of the more prominent towns with multiple lodging and dining options are Chestertown and Chesapeake City. Both can be reached by boat or automobile.

With a population of under 6000, Chestertown is the region’s largest community. The historic downtown has a vibrant Saturday farmer’s market as well as any number of small, local shops and eateries. The tree-lined roads that extend from the town center to the city docks are lined with shade trees and large Victorian houses. It is also home to Washington College, which lends the town a modestly academic feel.

Chestertown’s Spring farmer’s market

Chestertown’s Spring farmer’s market

Chesapeake City

Chesapeake City

Chesapeake City offers attractions completely out of proportion to its official population of less than 1000. Located on the Chesapeake and Delaware Canal, it is also an ideal stopping-off-point for boat traffic. Bohemian Avenue and Second Street in the historic downtown area are home to a plethora of shops, high-end restaurants and quaint Inns. Whether you park your car or moor your boat, everything can be explored by foot.

Must-Visit Wineries

There are a total of 18 wineries on the Eastern Shore and about half of them are clustered in the northern part of the region. All of them are worth a visit, but a few are worthy of note.

Crow Vineyard

Crow Vineyard


Crow Vineyard and Winery and Chateau Bu-De Bohemia Manor Farm are easily two of the Mid Atlantic’s leading producers. Not far from Chestertown, Crow Vineyard was a dairy farm for three generations before grapes were planted in 2010. Wines of distinction include the Sauvignon Blanc, Cabernet Franc, Barbera and Bordeaux blend. Owners Roy and Judy Crow also run a lovely little bed and breakfast. It should be noted that the winery operates a shuttle to and from Chestertown that is geared toward transporting visitors who arrive by boat.

Bohemia Manor Farm is located closer to Chesapeake City on land that was once part of the historic tract awarded to Augustine Herrman by Lord Baltimore in the mid seventeenth century. Owner Brenda Dedrick transformed a piece of her 440-acre estate into Chateau Bu-De. In the process, no expense has been spared to create a state-of-the-art winery. There is a bit of experimentation taking place as winemaker Jacques van der Vyver looks for a style that is uniquely Maryland. The Sauvignon Blanc, Grüner Veltliner and Cabernet Franc are exceptional, but all of the wines are well crafted. In addition to the wine, views of the Bohemia River are not to be missed.

Two relative newcomers worth keeping an eye on are Casa Carmen Wines and Broken Spoke Winery. Both are near Chestertown and pour wines of an extremely high quality.

Easy Access from Major Eastern Cities

The Rivers to Canal Wine Corridor is easily accessible from most major east coast cities. The proximity to Baltimore, DC and Philadelphia make this an attractive weekend drive. Even New York City is less than three hours away.

Planning Your Visit


Chestertown Tourism Information

118 N. Cross Street, Chestertown, Maryland 21620; (410) 778-0500; office@chestertown.com

Chesapeake City Tourism Information

P.O. Box 5, Chesapeake City, MD 21915; info@ChesapeakeCity.com


A complete list of Maryland’s Eastern Shore wineries is available at EasternWineTourist.com.