James Charles Winery & Vineyard – Winchester, VA
1582 N Frederick Pike, Winchester, VA 22603
James Charles Winery & Vineyard is a premier family-owned winery located in Winchester, Virginia. The vineyard produces a variety of handcrafted wines using grapes grown on their estate and sourced locally. Visitors enjoy wine tastings, tours of the vineyard, and an inviting tasting room atmosphere. The winery emphasizes sustainable farming and traditional winemaking techniques to deliver rich, flavorful wines. It serves as a popular destination for wine lovers and tourists seeking an authentic Virginia wine country experience.
Interesting Facts:

Wine Tastings
Wine tastings at James Charles Winery & Vineyard invite guests to explore a diverse array of handcrafted wines made from estate-grown and locally sourced grapes. Each tasting session is led by knowledgeable staff who explain the unique characteristics of each wine, including flavor notes, aging processes, and ideal food pairings. Visitors can savor reds, whites, and seasonal specialties in a relaxed and inviting atmosphere that encourages discovery. The tasting room’s ambiance is warm and welcoming, perfect for both first-time tasters and seasoned oenophiles. Guests enjoy the opportunity to ask questions, learn about winemaking, and connect with fellow wine lovers. Tastings often highlight new releases and award-winning vintages, making each visit unique. The experience offers a balance of education and enjoyment, ideal for small groups or solo visitors. Additionally, tastings can be paired with local cheese and charcuterie boards to enhance flavors. Visitors leave with a deeper appreciation of Virginia wines and a chance to purchase favorites to take home.
Vineyard Tours
The vineyard tours at James Charles Winery & Vineyard offer an immersive look at the entire winemaking process, starting from the grapevines themselves. Guided by expert staff, guests walk through the sprawling vineyards while learning about sustainable farming techniques that protect soil health and promote vine vitality. The tour covers the annual lifecycle of the grapes, from planting to harvest, and explains how the terroir shapes the wine’s flavor profile. Visitors gain insight into the winery’s commitment to quality and environmental stewardship. The tours often include stops at the production facilities where grapes are crushed, fermented, and aged. This hands-on educational experience connects guests to the heritage and craftsmanship behind each bottle. The serene vineyard setting provides a picturesque backdrop perfect for photos and moments of reflection. Guests often comment on how the tour enhances their overall tasting experience by providing context and stories. The walking tour is suitable for all ages and fitness levels, making it accessible and enjoyable for everyone.


Private Events and Weddings
Hosting private events and weddings at James Charles Winery & Vineyard offers a unique and memorable setting surrounded by natural beauty and rustic elegance. The venue features both indoor tasting rooms and outdoor garden spaces, allowing for flexible event planning that suits various styles and sizes. The winery’s dedicated event team works closely with clients to customize every detail, from decor and seating to catering and wine selections. Guests enjoy breathtaking views of the vineyard while celebrating in an intimate and inviting atmosphere. The combination of fine wine, scenic landscapes, and personalized service ensures a seamless and unforgettable experience. Whether it’s a romantic wedding ceremony, a corporate retreat, or a milestone celebration, the winery provides a sophisticated backdrop with a touch of charm. Event attendees can also partake in wine tastings and vineyard tours, adding a unique dimension to the occasion. The venue accommodates seasonal events, capturing the beauty of Virginia’s changing landscape year-round. Couples and hosts appreciate the attention to detail and warm hospitality that define events here.
James Charles Winery & Vineyard, Virginia Taxi
We provide vineyard shuttle services, airport transfers, wine tasting tours, corporate event transportation, and private group charters.