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Eastern Shore Food & Wine Weekend

    Fri, January 21, 2022 to Sun, January 23, 2022 (4:30 PM - 9:30 PM)

Great Oak Manor
10568 Cliff Road
Chestertown, MD 21620
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Cost: $50 +++

Join us for a one of a kind Eastern Shore food and wine weekend at Great Oak Manor. Arrive Friday evening to sip samples of Crow Vineyard’s award-winning wine while enjoying a cheese and charcuterie board before sitting down to a Soup Supper. Enjoy your Saturday around the manor property or head out to Chestertown for some shopping and sight-seeing. Saturday’s dinner will begin with a local wine tasting from Crow Vineyard and Love Point Vineyard with appetizers before sitting down to a 3-course family-style meal.

Friday’s Wine Tasting & Soup Supper – $50/pp | $100/couple*

Friday – 5pm Wine Tasting, 6:30 Dinner

Saturday’s Wine Tasting, Apps & 3-Course Dinner – $80/pp | $160/couple*

Saturday – 5pm Wine Tasting & Appetizers, 6:30 Dinner

* + tax and gratuity

 Wine by the bottle can be purchased prior to each dinner

 Dinners prepared by Chef Barbara Esmonde

 Wine provided by Crow Vineyard & Winery and Love Point Vineyard & Winery

 Limited seating for Saturdays dine-in only guests

Your weekend get-away would not be complete without your luxury room. Pricing varies depending on room. Guests participating in the Food & Wine Weekend will recieve 15% off their total room rate (Friday and Saturday night).

For more information, to purchase tickets and lodging, please call 410.778.5943

More information:


  • food
  • wine
  • eastern shore
  • getaway
  • local
  • Things to do in Chestertown, MD
  • Maryland Wine & Food Events
  • Chestertown Wine & Food Events

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Great Oak Manor

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