“People thank me for letting them sit out here,” notes Judy Crow, co-owner of Crow Vineyard and Winery. As I gaze at the flourishing fields from the sunroom of their Farmstay Bed & Breakfast, I think she’s right. There’s something peaceful about slowing down to enjoy the countryside. And that’s exactly what Crow Vineyard is about.

Crow Vineyard’s Dedication to the Land
Third-generation farmers Roy and Judy Crow are devoted to their Kent County, Maryland farm. Over the years, they’ve grown soy, wheat, and corn on the 365 acres and raised dairy cattle. Recognizing the need to diversify, Roy transitioned into an Angus beef farm around 2010.
The vision expanded to include a delightful three-room Bed & Breakfast and vineyard. The Crow’s son Brandon focuses on growing grapes, which winemaker Michael Zollo turns into award-winning wines.
I loved that the Crow’s repurposed a section of the milk barn into an intimate space for monthly wine dinners. The hay barn transformed into a sunny tasting room with an outdoor patio facing rows of leafy grapevines. As I sipped a glass of dark-fruit-forward Malbec, I felt like I was part of a modern-day working farm.

Wine Farming
Crow Vineyards believes in farm-crafted. They proudly grow their own grapes and source only locally, when needed. Over fourteen years of wine farming, Michael and Brandon developed protocols to ensure sustainable practices.
You’ll find Vidal Blanc, Barbera, Chardonnay, Sauvignon Blanc, Malbec, Merlot, Pinot Gris, and Cabernet Franc flourishing in Maryland soil. Inside the tasting room, my husband and I enjoyed a seasonal wine flight featuring six wines. Judy, Roy, and their attentive staff shared what they love about the vineyard with each pour.
Farm to Table Dinners
The Crows collaborate with Robbie Jester, an award-winning chef from the Food Network and Netflix, to host multi-course wine dinners that feature the best of Kent County. Robbie focuses the event on storytelling and local products. According to Robbie, his dinners focus on presentation that’s fanciful, not fancy.
Our dinner started in the wine production facility with the unveiling of a new vintage. As winemaker Michael described the vision behind the wine’s tropical notes, Robbie passed a chilled shot glass of refreshing corn vichyssoise with burnt tortilla gremolata and Aleppo gastrique. The tone was set for a magnificent dinner.

Over the next six courses, Robbie and Judy shared memories and the significance behind each dish. My husband and I indulged in the gorgeously creative food. My favorite was the Kitty Knight Crab paired with the 2024 Rosé. The recipe, consisting of crab-filled cannelloni, split peas, sherry, and an updated tomato soup, paid homage to the Kitty Knight House where Robbie’s father started his career as a chef.
Crow Vineyard and Winery’s Cozy Farm Stay

My husband and I settled into the comfy Vineyard Room after our delightful dinner. We contemplated waking up to feed the barn cats, cows, and chickens at 7.30 am. All guests are welcome to participate in the daily farm activities.
Instead of waking early, my husband and I spent the morning with a cup of coffee chatting with Judy between her homemade breakfast frittata and roasted potatoes and turnips from the garden. She graciously shared family photos and mementos from the Crow Farm and inspired us with her authenticity.
“Having cattle around and having open land is important to people, too,” noted Judy. A visit here reminds you that honoring the terrain and personal connections truly matter.

If You Go
Crow has numerous activities throughout the year, including Vineyard Walks, a fall Grape Stomp, and Murder Mystery Dinner. You’re welcome to enjoy the pool in the summer, explore the grounds, and take the trail to the pond.
I’m personally looking forward to trying Burger Night. Roy works the grill and cooks up Crow Angus beef burgers with all the fixings. Dinner includes two sides, dessert, and a glass of wine or sangria.
If you plan to attend a wine dinner, note that the Milk House seats about 8 guests. I recommend reserving in advance. Judy also requests reservations for Burger Nights.
Crow Vineyard is located near Chestertown, Maryland. The town is hopping on Saturdays with a vibrant farmer’s market. My husband and I took a stroll by the Chester River and enjoyed the 18th-century home fronts. Check out Modern Stone Age for a meal where everything from the pastries (get the chocolate croissant!) to the cheese, butter, and sandwiches is either made in-house or sourced locally.
Crow Vineyard and Winery hosted the writer and her husband.
Crow Vineyard & Winery, LLC
12441 Vansants Corner Rd.
Kennedyville, MD 21645

