Discover the Best Wineries on Maryland’s Eastern Shore

It’s true, that California’s Napa Valley is well known for its amazing wineries. However, did you know we have some exceptional wineries on Maryland’s Eastern Shore? In fact, there are over 80, with the oldest established in 1945 — Boordy Vineyards in Baltimore County. Our region produces varieties such as Cabernet Sauvignon, Cabernet Franc, Petit Verdot, Chardonnay, Norton/Cynthiana, Chambourcin, Vidal and Seyval.

When you think of Maryland’s Eastern Shore, images of scenic landscapes, charming small towns, and the stunning Chesapeake Bay likely come to mind. However, this picturesque region is also home to a thriving wine scene. Maryland wineries offer delightful tastings, beautiful views, and an immersive experience of the world of viticulture.

To make your visit even more special, book your room at the enchanting Brampton 1860. Our luxurious historic estate provides the perfect base for your wine-tasting adventures. We’ve started with our five favorite wineries. As you continue reading, we’ll share several other wineries on the Chesapeake Wine Trail. It’s an Eastern Shore wine lover’s paradise.

Eastern Shore Wineries Google Map

We’ve also created a Google map with our favorite wineries marked with red pins and the other wineries mentioned below with blue pins. We thought this would be a convenient way to create your own wine trail.



Five Favorite Wineries on the Eastern Shore (Red Pins)

1. Crow Vineyard & Winery

Crow Vineyard & Winery is our “partner in wine.” 😉 Choose from two options to savor their delicious wine and more.

  • Wine Country Date Night Special: Enjoy a stay in our charming countryside estate, a wine tasting, dinner for two, and more.
  • Grapes to Glass Tour & Tasting Experience: Enjoy a private guided tour exploring their farm. Indulge in a wine tasting paired with locally sourced produce and cheese mongers.

Crow is a family-owned establishment in Kennedyville that perfectly blends tradition and innovation. It’s known for its commitment to sustainable farming practices and offers a diverse range of wines, including its award-winning Barbera and Vidal Blanc. The rustic charm of the farm, combined with its amazing grass-fed Angus herd, truly makes this a must-visit winery.

2. Casa Carmen Wines

Casa Carmen Wines is a lovely bodega nestled in the heart of Chestertown. Carmen’s offers a selection of delicious tapas paired with its signature Spanish-style dry wines. This winery strongly emphasizes using traditional methods, producing wines that are distinctive and full of character. The cozy, intimate tasting room and the engaging stories behind each bottle add a personal touch to your visit.

The Duende is a favorite of ours, as well as the Vermouth. Enjoying a glass on the bodega’s front porch is hard to beat on a warm summer evening.

a collage of several wine bottles, someone pouring wine at a table, and two people clinking glasses of wine

3. Broken Spoke Winery

Located in Earleville, Broken Spoke Winery takes a fun approach to its wines and labeling — you just can’t help but smile! Broken Spoke is known for its fruit-forward wines. It’s Rumors and Blah Blah Blanc are crowd favorites.

We particularly enjoy their rosé selection. The laid-back atmosphere and picturesque surroundings make it an ideal spot to relax and enjoy a leisurely afternoon — especially with a flight of their delightful rosés.

4. St. Michaels Winery

St. Michaels Winery, situated in the heart of downtown St. Michaels, offers a diverse selection of wines that cater to all tastes — from robust reds to crisp whites and delightful rosés. The tasting room is in a renovated flour mill, creating a unique ambiance.

The “Martha” Chambourcin is near the top of our list and a great reason to take a little day trip for a lovely wine-tasting and delicious lunch.

5. Far Eastern Shore Winery

Finally, if you’re looking for something a little different, Far Eastern Shore Winery is a “must-try” choice. It’s based in Easton and specializes in rich, flavorful dessert wines — perfect for those with a sweet tooth. Their offerings are eclectic blends like the Spiced Apple and Chocolate Zinfandel, which are sure to leave a lasting impression.

The Lotus is a perfect dessert wine to pair with something yummy from one of the local bakeries!

That completes our top 5 wineries in Maryland. But wait, there are still some additional wineries that would be great to add to your list.


someone pouring red wine into goblets and one person swirling the wine in the glass


Other Notable Wineries on the Chesapeake Wine Trail (Blue Pins)

Bordeleau Vineyards & Winery

To begin with, Bordeleau Vineyards & Winery, located in Eden, is the furthest from our inn and offers a serene setting along Wicomico Creek (as their name reflects — “the water’s edge”). Their estate-grown wines are crafted with care, and their tasting room provides stunning water views. Highlights include their Chardonnay and Meritage blends you can enjoy as you take in the natural beauty of their vineyards.

Cascia Vineyards & Winery

On Kent Island, Cascia Vineyards & Winery combines beautiful waterfront views with exceptional wines. Interesting to note that owner/winemaker Mark Cascia is an aerospace engineer. He’s used some of his process skills to help create award-winning wines. Cascia’s portfolio includes “something for everyone” with a variety of reds, whites, and dessert wines.

Dove Valley Vineyard

Dove Valley Vineyard in Rising Sun is a multi-generational family farm. The winery grows a variety of grapes producing an award-winning selection of dry reds to sweet whites. The vineyard’s rustic charm and live music events make it a lively destination.

Lands Point Winery and Vineyards

Located in Cambridge, Lands Point Winery and Vineyards started as a hobby but has grown to produce high-quality wines reflecting the unique Eastern Shore region. Tastings often include detailed explanations of the winemaking process, enhancing the experience.

Layton’s Chance Vineyard & Winery

Layton’s Chance Vineyard & Winery in Vienna offers a welcoming and family-friendly atmosphere. It has a large picnic area with outdoor games and a hiking trail, perfect for a picnic with friends and family, and of course, a wonderful array of dry and sweet wines.

Love Point Vineyards and Winery

Lastly, the Love Point Vineyards and Winery offers breathtaking views of the Chesapeake Bay. Their tagline says it all — “A winery built on love, for wine made with love.” The picturesque location is perfect for a romantic outing.

Triple Creek Winery

Triple Creek Winery, based in Cordova, is known for its unique and flavorful small-batch wines. The winery often hosts events like food and wine pairings, providing the ultimate culinary experience.


the king canopy bed and fireplace in the yellow room at brampton 1860


Brampton 1860: Your Wine Trail Homebase

After a day of exploring and wine tasting at these wineries on Maryland’s Eastern Shore, there’s no better place to relax and unwind than Brampton 1860. Our charming estate offers a historic manor house, delightful cottages, and acres of natural beauty to provide a tranquil place to relax and renew.

Our luxurious accommodations and top-notch amenities provide serene comfort. Upon arrival, enjoy a complimentary bottle of bubbly, savor a delicious breakfast each morning, and indulge in afternoon tea with delectable treats. The serene surroundings and pampering from our welcoming staff ensure a memorable and rejuvenating stay.

Book your room now and start planning your Maryland wineries visit.





Photo Credit:
© Giovanni Magdalinos
© gilaxia

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