Chesapeake Wine Trail on Maryland’s Eastern Shore

Not only does Maryland’s Eastern Shore offer an abundance of fresh seafood, beaches, wildlife and history, we also have a tantalizing wine trail…and Great Oak Manor is right in the middle of it. What better way to experience the beauty of the Chesapeake Bay area than with wine?
Surprisingly enough, the sandy and well-drained soil combined with the moderate climate has turned this region into a distinctive grape growing environment. Our wineries maintain the charming and intimate atmosphere as our boutiques and other unique mom-and-pop stores.
While there are several wineries along the Chesapeake Wine Trail, four of them are less than 30 minutes from Great Oak Manor. You can plan your entire visit around the wine trail, or visit a couple while you’re out taking in the historic sights of downtown Chestertown.
Following the trail from the north, the first would be Crow Vineyard and Winery, followed by Clovelly Vineyard, Salisa Winery, and Cassinelli Vineyards and Winery.

Crow Vineyard operates 12-5pm everyday and their tasting room offers a full array of hand crafted wines. In addition, you can add a pairing tray made from their local grass fed Angus beef and other farm grown items. If you’re coming to visit us from the north, we would encourage you to stop at Crow on your way to Great Oak Manor as guests who present their confirmation emails in the tasting room will receive a complimentary tasting!

12441 Vansant Corner Rd
Kennedyville, MD 21645
302-304-0551

Clovelly Vineyards is located on a beautiful bend in the Chester River and only offer tours by appointment. However, a majority of their wines are sold at area retailers, but that should not deter you from making an appointment to tour this third-generation farm established in 1959.

301 Clovelly Lane
Chestertown, MD 21620
410-708-1775

On top of operating as a winery and vineyard, Salisa also features Crimson Pizza & Wine Bar, where they welcome visitors to sample their wines and enjoy amazing food.

6346 Church Hill Rd
Chestertown, MD 21620

The furthest out from Great Oak Manor, but certainly not a far drive by any means is Cassinelli, a family-owned and operated boutique winery. On their 110-acre farm, they have Merlot, Chardonnay, Viognier, Malbec, Petit Verdot, and San Giovese vines. In addition to all those vines, visitors are encouraged to visit their Black Angus cows, two buffalo, and two donkeys! Tasting is $6 and you keep the etched glass.

3830 Church Hill Road
Church Hill, MD 21623
(410) 556-6825

Now, before we send you off to tour these local vineyards along the Chesapeake Wine Trail, we wanted to impart some wisdom on how to taste wine like an expert, or maybe just understand some of what the experts look for:

First, examine your glass; it should be about one-third full. Move on to your visual evaluation from there. Look straight down into the glass, hold the glass to the light, and finally, give the glass a tilt so the wine rolls toward its edges. If you’ve ever witnessed someone doing this, they’re looking at the wine’s complete color range. This will give clues about the density and saturation of the wine. A deeply-saturated, purple/black color might be a Syrah or Zifandel while a lighter, pale brick shade would be a Pinot Noir.

The side view of the wine shows you clarity. A murky wine might suggest chemical or fermentation problems or could simply be a wine unfiltered. A clear and brilliant wine with some sparkle is always a good sign.

When someone tilts the glass, they’re evaluating the wine’s age and depth. If the color looks pale and watery near the edge, it suggests a thin wine. If it’s tawny or brown (for a white) or orange/rusty brick (for red) then it might be oxidized or past its prime.
Now for the infamous swirl. What you’re looking for is if the wine forms ‘tears’ that run down the side of the glass, wines with good tears are wines with more alcohol, indicating they are bigger, riper, and more dense than those that do not.

These are just a few tips on how to taste wine and truly evaluate their flavors and other characteristics, but the wineries will also share their own tips and knowledge.

A trip along the Chesapeake Wine Trail accompanied by your stay at Great Oak Manor would be a wonderful way to celebrate an anniversary, birthday, event or just a lovely weekend getaway. We hope that you will stay with us and explore our region’s growing wine boom.