' James Charles Winery & Vineyard - James Charles Winery | Calendar of Events

Calendar of Events



Wood-Fired Friday |  Every Friday, 5-8pm Begins April 5, ends October 25

Wind down your week at the winery!

April through October in 2019, 3Fires Oven will have authentic wood-fired pizza available for purchase every Friday night from 5 - 8 PM!

3Fires Oven will make your custom pizza right in front of you in their unique brick oven - pair it with a bottle of your favorite wine


Teacher Tuesday| Every Tuesday Starting September 4-6pm

We want to celebrate those who enlighten our youth. We thank you, teachers, for your hard work and dedication. Join us Every Tuesday from 4:00-6:00 for $4 Seasonal Drinks!

*School ID is required

Blessing of the Vines | Saturday, September 21, 2019 promptly 1:00

Join James Charles Winery Saturday, September 21st for an European Tradition of the blessing of the vines. 

Reverend Bjon Lundberg from Sacred Heart Catholic Church in Winchester will bless the vineyard to ensure a bountiful harvest.

Blessing starts at promptly 1:00pm. A Complementary tasting immediately following in the tasting room.

This is a free event.

Adult-Only Halloween Bash| Saturday October 26, 2019 8-12pm

All ghosts, ghouls, goblins and zombies are invited for an evening of spooky fun at the winery, featuring fresh party beats from BKDJ Paramount and dancing the night away!

Come join us for an evening of wine, Sexi Mexi and fun as you boogie through the night as your alter ego. A glass of Witch’s Brew is included in your ticket. Additional glasses of Witch’s Brew are only $5 - it’s a spooky good deal!

Whatever your wear, make it funky and fabulous. There will be prizes for the best female costume, male costume and best couple’s costume. Costume judging will begin at 10 PM.

  • $18 a ticket in advance
  • $25 at the door (if the event is not sold out in advance)

                          GET YOUR TICKETS HERE


Oyster Bar| Saturday November 2, 2019 12-6pm

Join us for our oyster bar at James Charles!

Chef Cheryl Ashe, the “culinary gangster” extraordinaire of Sweet NOLA’s Southern Food Lounge, will be preparing locally-sourced oysters that you’ll love!

Each ticket includes a half-dozen oysters, and we’ll have the perfect wines available for pairing with these delicious east-coast delicacies available for purchase at the oyster bar.

In fact, oysters are one of the Fabulous Flavors of Virginia, one of those local delicacies that makes our beautiful state such a wonderful place to explore! Just like wine, oysters come in all different flavors and sensations depending on the region, so there’s always more to explore. Click here to learn more about what makes oysters so awesome!

Reservations are required by October 29, and you must be 21 years old or older to participate. Tickets will include a half dozen oysters. This event will go on rain or shine. We are unable to refund tickets for this event. Tickets are $16 per person.

                GET YOUR TICKETS HERE


USMC 244th Birthday Ball| Saturday November 9, 2019 6:30-11 pm

This event is open to United States Marines, past or present, and their guests. A semi-formal dinner will be followed by the cutting of the cake, dancing and cash bar.

James Charles Bogaty, a US Marine and this winery's namesake, invites you to celebrate the 244th birthday of the Marine Corps!

This event is not-for-profit - all proceeds will benefit Toys for Tots, and other organizations that benefit US military veterans. There will be a Toys for Tots collection box at the winery.

  • $70 per person
  • Reservations required by November 4th

                          GET YOUR TICKETS HERE


Veteran's Day Weekend| Saturday November 9 - Sunday November, 10 2019

In honor of Veteran’s Day, we want to thank our military, firefighters, and police!

All service men and women receive a glass of wine for $3 and a 10% discount on all other purchases! Thank you for your service!


Black Friday Escape| Friday November 29, 2019

Escape the stress and hassle of Black Friday and come relax at the winery!

We’ll have live music from 2-5pm and a very special pasta bar from 3Fires Oven from 12-4pm - the relaxation will last all day!


Christmas Tree Lighting Ceremony| Saturday December 7, 2019

Join us for our 5th annual lighting of the winery Christmas tree!

Everyone will receive a complimentary cookie and we have a special on glasses of mulled wine all night as we gather around the tree and see the lights go up - this event is great for kids, too!

We will light the tree at 7pm, but come early and stay late as we kick off the holiday season with live holiday music in the tasting room.

Psst! We also heard that Santa will making a stop by the winery from 7-8!


Free Shipping Friday| Friday December 13, 2019

Virginian wine makes the perfect holiday gift, and you can buy right from our website!

If you’re shopping for Christmas at the last minute and can’t make it to the winery, we’ve got you covered!

Friday, December 13 is Free Shipping Friday - get free shipping on any order until midnight so your holiday shopping is done for the wine lovers in your life!


 Tasting Room Hours

Monday - Thursday | Noon - 6 PM

Friday | Noon - 8 PM

Saturday | Noon - 7 PM

Sunday | Noon - 5 PM


Send an email to James Charles Winery     Get directions to James Charles Winery     Call James Charles Winery


James Charles Winery & Vineyard | 4063 Middle Road, Winchester, Virginia 22602

540-931-4386 | info@jamescharleswine.com


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