At Chesapeake Manor Vineyard, we believe wine is best enjoyed in good company and beautiful surroundings. Our estate features handcrafted wines, live music, seasonal events, and a welcoming atmosphere inspired by the Chesapeake Bay. Whether you’re here for a tasting or an afternoon escape, you’ll feel right at home.
Chesapeake Wine Trail
Chesapeake Wine Trail
Combining wines grown specifically to pair with Maryland’s unique seafood bounty with unforgettable views and the warm, welcoming spirit of the Eastern Shore, the Chesapeake Wine Trail is a must-see for every wine lover. While you’re here, explore the rich history of the region, home to American heroes such as Harriet Tubman and Frederick Douglass, whose indomitable spirits shaped our modern nation. Explore the bay on a Skipjack, the traditional oyster boat of the Chesapeake, and part of the only remaining sail-powered fishing fleet in North America.
And did we mention those wines? Taste the fruit of Maryland’s Atlantic Coastal Plain growing region and the labor and love of our artisan wine makers.
About Our Winery
Vineyard owner and winemaker Thomas R. Shelton has been growing grapes since 1999 on his Eden, MD property bordering the pristine Wicomico Creek. The...Recent Posts
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About Our Winery
Since our Grand Opening June 23, 2017, we have been eager to share our love of wine and agriculture. The Broken Spoke Family has...Recent Posts
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About Our Winery
Casa Carmen is a boutique winery on the Eastern Shore of Maryland, dedicated to crafting premium, local, dry wines. We are the closest winery...Recent Posts
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About Our Winery
Award-winning estate-grown wines on Kent Island in historic Stevensville, Maryland. Gather with friends on the Eastern Shore in a relaxed setting with friendly hospitality,...Recent Posts
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About Our Winery
The Tasting Room offers a full array of hand-crafted Crow Vineyard wines and you can add a cheese tray made from our local Grass-fed...Recent Posts
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Upcoming Events
Burger Night at Crow
6:00am, June 13Read More
Burger Night at Crow
6:00am, July 3Read More
Burger Night at Crow
6:00am, July 18Read More
Wine Seminar: Vineyard Walk & Appetizers With Chef Robbie Jester
5:00pm, August 15Read More
Grape Stomp
12:00pm, September 6Read More
Grape Stomp
12:00pm, September 20Read More
About Our Winery
Cecil County's First Vineyard and Winery ! Family owned and operated. Dove Valley grapes are grown by the head of the Chesapeake Bay, The...Recent Posts
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Upcoming Events
Derby at the Vineyard *Saturday June 27th*10am-5pm
11:00am, June 27Read More
About Our Winery
Far Eastern Shore Winery is a family-owned, boutique micro-winery located on the Eastern Shore of Maryland, in the historic town of Easton.Recent Posts
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About Our Winery
Lands Point is a small batch, family-owned winery producing dry red and white wines from grapes grown on site. Lands Point Winery & Vineyards...Recent Posts
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About Our Winery
After four generations of farming in the Salem area of Dorchester County as Lazy Day Farms, the Layton family decided to share their love...Recent Posts
Burning of the Vines tickets are now live!
One of our most exciting...Read MoreHoliday Hours
🎄 Holiday Hours Update 🎄...Read MoreLayton’s Chance Sweet 16 Birthday Bash
Layton's Sweet 16 Birthday Bash...Read MoreLive On The Porch!
🎶🍷 Live on the Porch...Read MoreLove At First Bite!
A Valentine's Day Wine &...Read MoreMenu Drop! Love at first Slice pairings
💕🍰 Love at First Slice...Read MorePimpin’ HOmicide
Murder Mystery Night 2026: Pimpin’...Read MoreSanta’s Panic Pop-Up
𝐒𝐚𝐭𝐮𝐫𝐝𝐚𝐲, 𝐃𝐞𝐜𝐞𝐦𝐛𝐞𝐫 𝟐𝟎𝐭𝐡 • 𝟏𝟏𝐀𝐌–𝟑𝐏𝐌...Read More🎶✨ Concerts in the Country at Layton’s Chance! ✨🎶
From May through August, join...Read More🥚🐰Just over ONE WEEK AWAY from our Adult-Only Easter Egg Hunt!🥚🐰
The countdown is on! In...Read More
Upcoming Events
Layton’s Chance Sweet 16 Birthday Bash
12:00pm, May 23Read More
Adult Field Day – Vineyard Water Wars!
12:00pm, June 13Read More
Concerts in the Country – June ft. Black Dog Alley
6:00pm, June 20Read More
Concerts in the Country – July ft. Uprizing
6:00pm, July 18Read More
Concerts in the Country – August ft. Days of Vinyl
6:00pm, August 15Read More
About Our Winery
Waterfront winery offering artisan crafted award wining wines. We have an expansive view of the Chester river for you to enjoy a number of...Recent Posts
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About Our Winery
Mark Cascia Vineyards grows over 12 acres of premium wine varietals on Kent Island on Maryland's Eastern Shore. Cascia Vineyards is a unique, family...Recent Posts
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About Our Winery
St. Michaels Winery is located in the quaint, waterfront town of St. Michaels on Maryland's Eastern Shore. We uncork daily at 11am and are...Recent Posts
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