' James Charles Winery & Vineyard - James Charles Winery - Wine Tastings & Tours - Winchester VA

Tasting & Tours


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Classic Wine Tasting

An opportunity for you to sample all of James Charles' red- and white wines which are currently available. Compare, contrast, and explore your taste selections at the tasting bar.

  • This tasting lasts approximately 30 minutes
  • For any group of seven guests or less, $12 per person, no appointment required
  • For groups of eight guests or more, $18 per person, and advance reservations and payment required. Please call the tasting room at 540-931-4386 or email us to make arrangements.


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Vintner's Table Seated Tasting

Enjoy exclusive table service, complete with a Charcuterie food pairing, at the Vintner’s Table in our tasting salon with one of our experienced wine consultants. The Table offers leisurely reserved seating while you savor our wines and take in the spectacular view of the Shenandoah Valley.

  • This seated tasting lasts approximately one hour
  • Minimum of 4 people required
  • Vintner's Table can accommodate 4-8 guests
  • $30 per person
  • Reservations and payment required at least three days before the desired date, available on weekends only


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Things to know before your visit to James Charles


  • Monday - Thursday | 12:00pm - 6:00pm
  • Friday | 12:00pm - 9:00pm
  • Saturday | 12:00pm - 7:00pm
  • Sunday | 12:00pm - 5:00pm


  • We welcome your group to share a quiet outing at our winery and enjoy the beautiful views.
  • For larger groups (8 people or more), we'd be happy to accommodate you! Please call our main office at 540-931-5452 at least 48 hours in advance of your visit to make reservations.
  • To make tasting reservations for large groups, we require payment at the time the reservation is made. Reservations will be guaranteed for up to 20 minutes after schedule time. Reservations must be cancelled 24 hours in advance.


  • We sell a selection of gourmet foods in our tasting room, including fresh baked bread, cheeses and salami and several lite fare menu options.
  • Food brought with you to James Charles is to be kept on our outdoor areas only and is not permitted in our tasting room.
  • For larger groups (over 8 guests) we ask that you enjoy your picnic on our picnic grounds and not our terrace. If you would like to rent a table to accommodate your party please call 540-931-5452 or email info@jamescharleswine.com.


  • When planning to visit James Charles winery, please remember that the only alcohol that is permitted is wine purchased at James Charles. This is a law and is regulated by Virginia Department of ABC.
  • Please do not bring any other alcohol including but not limited to previously-purchased James Charles Winery & Vineyard wine, wine from another vineyard, beer, hard alcohol, champagne or wine coolers. Violators will be asked to leave the property immediately.


  • Your friendly four-legged friends (on leashes) are welcome on our grounds, but not in our tasting room. (Exception: service dogs are always welcome anywhere on our property, including inside)


  • James Charles is a smoke-free environment. No smoking or vaping is allowed anywhere on the premises.


Bocce Ball Court

Bocce is an increasingly popular activity, and for good reason: you can play while you're enjoying a glass of your favorite wine! 

The bocce court at James Charles is a destination for lovers of the games in Winchester, VA and in the northern Shenandoah Valley. 

It's free to play! Ask a wine server to provide the balls to play. 

We expect all players to respect the rules posted next to the court. 


How to Play Bocce      


Our tasting room is on Middle Road, only five miles from Old Town Winchester



Monday - Thursday | Noon - 6 PM  //  Friday | Noon - 9 PM  //  Saturday | Noon - 7 PM  //  Sunday | Noon - 5 PM


4063 Middle Rd, Winchester, VA 22602


info@jamescharleswine.com // 540-931-4386