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

Calendar of Events



Live Music  |  Every Saturday & Sunday

2:00 - 5:00 PM -- Every Saturday from 3-6pm and Sunday from 2-5pm, JCW brings in some of the most talented musicians in the Shenandoah Valley. With no cover charge and a front-row seat to these talented artists, come and immerse yourself in great music with a glass of JCW Virginia wine!
Chris Hammock| Saturday, February 23 ... Acoustic Soul | Sunday, February 24


Mulled Wine Mondays  |  January 7th- March 25th

Warm up this Winter with “Mulled Wine Mondays”!

Visit with us on Monday’s from January 7th through March 25th to receive a glass of Mulled Wine at Half Price!


Hurry In, this deal is almost too good to be true and is only available while supplies last!


The Sid Sessions |  Saturday February 24, 2019

Join us for “The Sid Sessions” on February 24 from 3:00pm-4:00pm with none other than Sid Peters! Grab your glass of wine and listen to Sid discuss “The Secret”-A motivational, Feel good and change your life book.


Tickets are $6 and includes the session and a Free glass of our James Charles Wine! Reservations required in advance. CLICK HERE





Mac ‘n’ Cheese & Wine Pairing |  Saturday March 9, 2019

Come experience wine and cheese in a new way with our macaroni & cheese wine pairing!

This is a self-guided pairing of Virginian wine and four gourmet mini mac ‘n’ cheese bites!  

 Your pairing will include a taste of classic mac, our gruyere mac topped with bacon crumbles, our pesto mac, and spicy sriracha mac. Each mac & cheese sample comes with a healthy tasting of a wine.  This tasting also comes complete with a pairing guide, all for just $18!

**This event is SOLD OUT at James Charles Winery. Don't forget our sister vineyards are having the event too. If the time slot you want is sold out feel free to attend the event at Bodagi Bodea or Veramar Vineyard. Ticket links here:
Veramar Mac N Cheese: https://veramar.xudle.com/res-416157/Mac-And-Cheese-Pairing.html
Bodega Mac N Cheese: https://shop.bogatibodega.com/res-416924/Mac-And-Cheese-Wine-Pairing.html




St. Patrick’s Day with Brandy Stills Band |  Saturday March 16, 2019

Brandy Stills Band rocks out the afternoon of St Patrick's Day in the James Charles tasting room!

St. Patrick’s day is not just about green beer! How about some Irish cheer, Virginia wine and Brandy Stills Band? Plus, 3Fires Oven will have their magnificent pasta bar open from 12-4pm!

This St. Patty’s Day, come on out to James Charles Winery and enjoy a custom-made pasta and Glasses of James Charles Wine are only $5 all day long!

Then at 2pm, grab a seat in the tasting room the for live music with local Brandy Stills Band! So grab your friends and celebrate the St. Patrick’s Day at James Charles Winery!

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


Adults Only-Easter Egg Hunt |  Sunday, April 14, 2019-2:00pm

This event at James Charles Winery is SOLD OUT- Please see our sister vineyard- Veramar Vineyard for the same event and tickets: CLICK HERE

Kids shouldn’t be the only ones who have fun on Easter! James Charles is offering an adults-only twist on this fun tradition!

On Sunday, April 14th, you will scour the vineyard hunting for eggs we’ve hidden carefully all over the property!

These eggs will contain tasty treats and more grown-up prizes like gift certificates, free tastings vouchers, free wine glasses, James Charles swag and other great prizes! You might even find a Golden Egg!

Reservations required in advance, and you must be 21 or older to participate. Text your friends and kick off springtime with a fabulous day of fun!





Mother’s Day Picnics |  Sunday, May 12, 2019

Treat you mom to a Mother’s Day picnic at the vineyard! Spend the day with Mom surrounded by the quaint elegance of James Charles Winery.

There are three options for your picnic:

  1. Tarragon chicken salad mixed with grapes, toasted pecans, tarragon, celery, mayonnaise and baby lettuce mix
  2. Pit ham with Brie cheese, Granny Smith apples, baby lettuce mix and Dijon mustard
  3. Baby organic spinach with hummus, roasted red peppers, shaved carrots, sliced tomato, feta cheese, balsamic glaze and extra-virgin olive oil

Each wine-country Mother's Day picnic will include a side salad of baby lettuce topped with tomato, cucumber, Kalamata olives, feta cheese and red-wine vinaigrette.

It even includes a dessert: rockslide brownie bar topped with caramel, toasted pecans, brownie chunks and caramel ganache.

Then at 2pm, grab a seat out on the terrace the for live music!

So leave the planning for your Mother’s Day outing to us, and we’ll have your picnic ready for you when you arrive.

$25 per person.

Reservations required by May 8.



Health Professionals Appreciation Weekend |  Saturday, May 18 and Sunday, May 19

Calling all health professionals!

We want to thank you for all that you do! You’ve worked hard all year taking care of people, so it’s about time that someone takes care of you.


James Charles is just the place to go this weekend! Visit the winery and we’ll give you a glass of your favorite James Charles  wine for just $3 when you show your professional ID!

Invite your colleagues and join us for an awesome weekend of celebrating your hard work!


Teacher Appreciation Weekend |  June 7th-June 9th

Calling all teachers!


We want to thank you for everything that you do! You’ve worked hard all year educating our children.


So if you’re a teacher, James Charles Winery is just the place to go this weekend!


Come to James Charles Winery and we’ll give you a glass of your favorite James Charles wine for just $3 when you show your school ID!


Invite your colleagues and join us for an awesome weekend of celebrating your hard work!


Champagne Flutes and Cowboy Boots-Dance |  Saturday, June 8 

Join James Charles Winery for our First Ever “Champagne Flutes and Cowboy Boots Dance”!

Come dressed in your Country best and get ready for a night of Champagne and Dancing!

Tickets are only $18 in advanced and will be available at the door for $20!

Sexi Mexi will be there with their signature Burritos and bowls-Will you be there?!





New Orleans Festival |  Saturday, June 22, 2019 12pm-6pm

With authentic New Orleans cuisine like alligator on a stick from Sweet NOLA’s and live Music from The Voodoo Blues, we’re bringing the French Quarter to Winchester!


Veramar Vineyard and Bogati Winery will be pouring wine at this event as well!

Your ticket includes Mardi Gras beads and a souvenir JCW wine glass!

Plus, glasses of Frosé are only $5 all day!

Laissez les bon temps rouler" (pronounced "Lay-say le bon tom roo-lay") means "let the good times roll” and that is what we are going to do!

This event will go on rain or shine. No picnics or pets allowed at this event.

Tickets are $15 in Advanced and $20 at the door!


(Due to the popularity of this event, lawn chairs are recommended.)


GET YOUR TICKETS HERE: http://bit.ly/NewOrleansFest19


4th of July Celebration |  Thursday, July 4, 2019 1pm-6pm

Celebrate freedom at James Charles Winery with live music from 1pm to 4pm!

All James Charles Wines, including our signature Frose will be $5 all day long!

We hope to see you there!


Ice Cream and Wine Pairing |  Saturday, July 6, 2019

Come experience wine and ice cream in a new way with our ice cream and wine pairing!

This is a self-guided pairing of Virginian wine and four delicious ice cream flavors!  

Each ice cream sample comes with a healthy tasting of a wine.

This tasting also comes complete with a pairing guide, all for just $18!


GET YOUR TICKETS HERE: http://bit.ly/IceCreamAndWine


Drunken Watermelon Festival |  Saturday, July 27, 2019 12pm-6pm

Celebrate Summer with our first ever Drunken Watermelon Festival!

Come out to James Charles Winery on July 27th to enjoy Live Music, Watermelon White Wine Spritzers, Hog it Up BBQ, and of course-James Charles Wine’s!

We will also have our “Watermelon Games”-Pre Purchase tickets for $2 a piece to participate in:

  • Watermelon Bowling-How far can you roll?
  • Seed Spitting-How far can you spit?
  • Watermelon Eating-How fast can you eat?

Want to participate in all 3? Sign up for all 3 events for only $5!

**Reservations for events are required in advance**

No outside food or pets allowed. Event will go on Rain or Shine. Lawn chairs are recommended.


GET YOUR TICKETS HERE: http://bit.ly/DrunkenWatermelon


Perseid Meteor Shower Watch Party |  Saturday, August 10, 2019  7-11pm

We’re staying open late on Saturday, August 10th to watch the Perseid Meteor Shower over the Valley, and we hope you’ll join us for the fun!


Come out for an evening under the shooting stars and enjoy delicious food brought to you by Sexi Mexi and of course, James Charles Wines!


We’ll have live music starting at 7pm and lots of good vibes as we stay up late to watch shooting stars pepper the sky!

Lawn chairs and/or blankets are recommended so you can get the best view of the sky.


Blanc on Blanc Dinner Party|  Saturday, August 24, 7-11pm

Join the Blanc on Blanc movement! Bring your significant other for our 4th annual Blanc on Blanc dinner party!

Your ticket includes an elegant dinner, live music, dancing and a glass of wine.

There’s only one rule for Blanc on Blanc: wear all white!

Get creative! Dig those fancy white suits and blazers and dresses out of the closet and put together a fabulous outfit.


Tickets are limited**


This is an assigned seating event: Email info@jamescharleswine.com if you want to request group seating.

GET YOUR TICKETS HERE:http://bit.ly/blanconblanc2019


Labor Day Celebration|  Saturday August  31, 2019 12-7pm

Celebrate hard-working Americans and treat yourself to a day of relaxation this labor day weekend!

This is a FREE event featuring live music and delicious food from Sexi-Mexi Burritos food truck.

Celebrate your long weekend with savory eats, great music and refreshing James Charles wine!

 Tasting Room Hours

Monday - Thursday | Noon - 5 PM

Friday | Noon - 9 PM

Saturday | Noon - 8 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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