Gringo Gordo Empanada Brunch Bar

James Charles Winery 4063 Middle Road, Winchester, VA, US

Dive into a delectable morning of culinary delight and sparkling toasts at James Charles Winery this March 3rd! Our Brunch Bar is the perfect weekend escape, blending exquisite flavors with the joy of good company. Savor the Flavor: Indulge in a mouth-watering selection of breakfast empanadas, crafted with love by Gringo Gordo, Winchester's culinary gem. ... Read more

Local Chili & Wine Pairing

James Charles Winery 4063 Middle Road, Winchester, VA, US

Taste locally-crafted chili and cornbread by Uncle Buddy's Catering while you relax with a glass of James Charles's finest wine! Ticket includes a 12 oz. bowl of chili, cornbread, and a complimentary glass of wine. Club members: enjoy your standard discount of 20% on all purchases! Tickets

ValenWine’s Day

James Charles Winery 4063 Middle Road, Winchester, VA, US

Treat your love to ValenWine’s Day on February 10th! From 2 – 5 PM, relax to local live music with a plate of petite, chocolate-covered sweets and a choice glass of your favorite wine. Ticket includes: Variety of petite sweet treats with your choice of a glass of wine or sparkling. Club discounts apply. Music ... Read more

Christmas Tree Lighting

James Charles Winery 4063 Middle Road, Winchester, VA, US

The time of year to deck the halls is approaching fast and our tasting room needs a little extra Christmas spirit this year, don't you think? On Saturday, December 2nd from 6-8 PM, we are lighting up our Christmas tree and we want you there to partake in the joyous fun. We will light the ... Read more

Live, Laugh, Lasagna (and Wine!)

James Charles Winery 4063 Middle Road, Winchester, VA, US

When wine is paired with an absolutely mouth-watering classic dish like lasagna, all is right with the world! Whether you need a break from shopping, or are looking for a family fun outing after a big holiday - we will have you covered with our nice and easy meal of lasagna and a glass of ... Read more

Watermelon Wine Festival

James Charles Winery 4063 Middle Road, Winchester, VA, US

James Charles Winery & Vineyard invites you to our very first Watermelon Wine Festival on August 26th from 12-6 PM. Join us in celebrating the vibrant and refreshing flavors of Summer with our uniquely crafted Drunken Watermelon Drink, live music, dancing to the Watermelon Crawl, and a full day of family-friendly fun and watermelon festivities. ... Read more

Live Music: Bruce Corsino

James Charles Winery 4063 Middle Road, Winchester, VA, US

Piano-Vocal recording artist Bruce Corsino will appear LIVE to belt out his versions of The Great American Songbook---the standards, blues, popular and Broadway tunes you know and love. This FREE show is sponsored by the James Charles Winery and Vineyard in the hills of Winchester, Virginia and one of the most stunning locations in the ... Read more

Local Art Show at James Charles

James Charles Winery 4063 Middle Road, Winchester, VA, US

Immerse yourself in an art exhibit at James Charles! Fine wine and exquisite art are the perfect pairing! We have asked local artists to come to James Charles on Sunday, April 30th to showcase their masterpieces! From 1-4 PM, our tasting room will be filled with amazing art to gaze upon while sipping our award-winning wine! Come ... Read more

A Night on Broadway

James Charles Winery 4063 Middle Road, Winchester, VA, US

There's no business like show business! Let us entertain you, let us make you smile! We have something special waiting in the wings at James Charles. We are taking a trip to Broadway and you are all invited to merrily roll along. With live performances featuring Broadway Ballads, Comedy & Showtunes Galore, A Night on ... Read more

The Brunch Bar

James Charles Winery 4063 Middle Road, Winchester, VA, US

You are invited to take part in our elegant Premier Event series, The Brunch Bar! Brunch is breakfast without an alarm clock. Let’s add some wine into the mix to glam it up a bit! Come and enjoy the beauties that a Sunday can bring with James Charles Winery’s event series, The Brunch Bar. The ... Read more

Click here to view more upcoming events on our Winchester VA Events Calendar.