Premier Events

We have a vision for grand, one-of-a-kind occasions. Browse through our finest events, and join us for an unforgettable experience. Look for our special logo when you go to book.

Our Premier Events at James Charles Winery will be held in our brand new Salon Room that is adjacent to the tasting room! We have been hard at work designing the perfect room to host events and we are very excited to finally bring it to you!


September 24th, 2022

Harvest Wine Dinner

You are invited to come and help us celebrate this year’s harvest with an elegant meal featuring food from Chef Michael Oehisen and James Charles wines!

Harvest season is the season for gathering to signify the beginning of Autumn.

This harvest season, we are joining together for a unique Harvest Wine Dinner! Join us in the newly renovated Salon Lounge at James Charles on Saturday, September 24th at 6:30 PM for an elegant, four course meal! Experience a delectable and locally sourced meal prepared by Chef Michael Oehisen. Each Farm to Table course will be perfectly paired with a James Charles wine.

The evening will begin at 6:30 PM with a complimentary specialty drink and hors d’oeuvres.

The Second Course of the evening will be served at 7 pm and will be an Arugula & Mesclun Salad with goat cheese, roasted garlic spiced walnuts and pickled red onion, tossed in a white wine lemon spritz.

The Third Course will be an option of either: (choices will be picked at checkout)

Orr’s Apple Cider braised/cherry wood smoked center cut pork tenderloin topped with a roasted plum chutney.


Orecchiette with pan seared Tiger Shrimp, roasted corn & chilis topped with a Crème Fraiche and fresh cilantro.

Each option will be accompanied with roasted Acorn Squash with caramelized walnuts and port hydrated cranberries, and fire roasted brussels sprouts & cherry tomatoes with grated aged parmesan.

The Fourth Course will be a Pumpkin Cheesecake Trifle with salted caramel & Bailey’s Pumpkin Liquor Cream.

Reservations for this four course wine paired meal are available for $90.00 per guest. Service fee includes meal tax and a 20% gratuity.  Seating is limited, so reserve a space now!

July 23rd, 2022

Expand Your Mind With Wine

Come out to James Charles on July 23rd at 7PM! Our comedy and mentalist show will leave you feeling astounded!

We have yet another intriguing experience waiting for you at James Charles newly re-vamped Salon Room! On Saturday, July 23rd, we are hosting an Expand Your Mind with Wine show!

This show will feature two outstandingly talented individuals.
Jani Tillery

The show will open with the hilarious comedian, from Jani Tillery. She hails from Bloomfield Hills, Michigan. She is a Washington D.C. based attorney and comedian who practices law by day and tells jokes by night. Jani has performed standup comedy around D.C., Maryland, and Virginia. Jani has also performed at comedy clubs and festivals around the country. She was recently featured in a Comedy show over at Bogati Winery in Round Hill and she was so funny that we had to have her come out to James Charles!

Christophe Fox

Our featured act will be the mentalist and magician, Christophe Fox. He could be spotted in our Vaudeville show this past April as the opening act where he wowed the crowd with his skillful mind-reading. Christophe is a corporate presenter, speaker, and entertainer. As the two-timer winner of Washington D.C.’s Magician of the Year, TEDx Speaker, and social media influencer- his talents are used in the service of helping clients host events with impact. His clients include The Four Seasons, Keller Williams, J.P. Morgan, McLean Mortgage, ENO, Pivotal Software, Fairway Independent Mortgage, The U.S. Military, BH Mid-Atlantic Inc, and – just to name a few.

He performs magic, mentalism, hypnotism and mind-reading!

Check out his website or book him for a show here!


Do these two sound as interesting to you as they do to us? Then come on out to James Charles Winery on July 23rd for an unforgettable evening. The doors for the show will open at 7PM and the show will begin at 8pm! There will be light fare and delicious James Charles Wine for sale!
Tickets for this unique show will be $25 for our guests and $20 for our Legacy Club Members!

Comedy Night at James Charles

You’re invited to the brand new Salon Room at James Charles Winery for a night full of laughter! Our very first Comedy Night will surely make your sides split! Grab your friends and get ready to laugh!

Good jokes paired with good wine can only bring out the greatest laughter.

Coming to the Salon Room for one night only, it’s James Charles’ very first Comedy Night!

On Saturday, June 11th, our brand new Salon Room will open its doors for a night of side-busting laughter and a good time. The doors for this event will open at 7 PM and the chuckling begins at 8 PM sharp! Seating will be open, so arrive early to get a good spot to view the show!

Our show will host two hilarious local comedians:

Mark Matusof

One of the top comics to come out of Washington D.C., Mark has been described in the press as “funny without being vulgar or nasty” and “going the smarter, hipper direction to the joke.” A first generation American, Mark’s material ranges from his immigrant family to the aggravations of modern life; from current events to the fragility of the male ego.  There’s even a little music tossed in for good measure!

Liz Barlow

Liz Barlow is a stand-up comic and writer from Virginia Beach, VA. She’s been seen on Zanies, Funny Bone and Comedy Zone stages. She’s a published essayist with several articles in the Huffington Post. If she isn’t telling jokes or moming, she’s probably handing out masks at the trap house.

Tickets for the show are $22 for general admission and $18 for our Legacy Club Members.

Show your confirmation email that you received after purchase upon arrival.

May 8th, 2022

Mother’s Day Brunch & Bubbly Bar

Grab your mom and get ready to pop some bottles in honor of her this Mother’s Day! James Charles will be hosting a very special Salon Room Premier Event with a Mother’s Day Bruch & Bubbly Bar!

Doesn’t your mother deserve the very best for this Mother’s Day? We think so!

To honor the hard work and dedication that each and every mother gives to her loved ones all year round, we are throwing her a Mother’s Day Brunch & Bubbly Bar in our brand new Salon Room at James Charles!

Bring the whole family in celebration of mom! We have two time slots to choose from. Come at either 10-11:30 AM or 12-2 PM for this unique brunch! Regular admission tickets will be $45 per person ($37 for Legacy Club Members) and children’s tickets will be $30 per person ($24 for Legacy Club Members).

All children must be 12 and under to qualify for a child ticket.

Each ticket will grant you access to this Premier Event with one complimentary mimosa from our bubbly bar and access to three gourmet food stations catered by The Catering Company to choose from!

Station One

Build Your Own Omelette

Omelet with Fresh Whole Eggs or Egg Whites

Choices Include: Applewood Smoked Bacon, Sausage, Ham, Grilled Onions, Charred Bell Peppers, Roasted Mushrooms, Baby Spinach, Chopped Tomatoes, Sharp Cheddar Cheese, Mozzarella, Hot Sauce, Salsa and Ketchup

Comes with a side of Hashbrown Casserole

Station 2

Shrimp & Grits

Bacon, Assorted Cheese, Andouille Sausage, Sundried Tomatoes, Green Chilies, Jalapeños, Diced Tomatoes, Chives, Cilantro

Station 3

Fruit, Yogurt & Pastries

Choices Include: Fresh fruit and yogurt parfait station, Assorted Danishes, Muffins, and Pastries

Non-alcoholic Beverages Include:

Orange Juice, Apple Juice, Cranberry Juice, and a Full Coffee Bar complete with various sweeteners, creamers, and flavored syrups


There will be additional wine, champagne and mimosas for sale. 

We will also be joined by K.Noel Boutique. This boutique is an Online & Mobile Boutique out of Stephens City, VA. Offering Stylish, Trendy, Everyday Apparel & Accessories for beautiful babes everywhere! {sizes S-3XL} Shop 24/7 on our mobile app or website!
Swing on by the truck to pick out something special for mom! Her truck will be at the winery from 10AM – 2PM.

April 23, 2022

A Vaudeville Variety Performance

We’ve got the most talented acts in Winchester lined up for a night of entertainment! Come by and witness James Charles’ brand new Salon Room’s first premier event: A Vaudeville Style Talent Show!

“The world’s a stage, and everything else is Vaudeville” -Alan Moore

The Vaudeville craze came to the US from France in the 1920’s. We wanted to bring a little piece of French history into our brand new Salon Room at James Charles with a modernized Vaudeville Show!

Vaudeville brings out acts of all kinds of talent and just wait until you see what we have in store. We have live performances ranging from dancing and music to magic acts! We also have various acts featuring students from Shenandoah University as well as many other astonishing performances! You surely won’t want to miss out on this dazzling display of talent!

On Saturday, April 23rd, the doors will open at 7 PM, the show will begin at 8 PM and will include a fifteen minute intermission. Seating options will be open, so come early to get a good spot and a tall glass of wine to enjoy the show with!

Tickets are $25 and $20 for our Legacy Wine Club Members. Upon arrival, please show your email confirmation that you will receive after you purchase tickets.

Reserve a spot and be prepared to feel amazed!

August 28, 2021

Blanc on Blanc

A dinner like no other. Arrive in your finest white attire and be prepared for a sit down meal designed by The Chef's Table, complimented by our first class wine. Afterwards, dance the night away under the light of the stars.

June 2021

The Pink Picnic

A full course gourmet picnic lunch at the heart of Virginia. Guests are encouraged to dress to match our rosé as we transform our vineyard into a paradise of pink.

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