SAVOR TRADITION, CELEBRATE LIFE
James Charles Winery & Vineyard
Elevated Virginia wine near Winchester, VA
James Charles Winery & Vineyard is a family-owned Shenandoah Valley winery in Virginia, known for elegant wines and scenic vineyard hospitality inspired by generations of the Bogaty family.
Address: 4063 Middle Rd, Winchester, VA 22602
Phone: (540) 931-4386
Hours: Mon–Thu 12–6 | Fri 12–7 | Sat 12–6 | Sun 12–5
Plan Your Visit
Plan your visit to James Charles Winery & Vineyard for a relaxed, family- and dog-friendly day in the Shenandoah Valley. Enjoy beautiful views, welcoming spaces, and regular live music while you sip Virginia wines. Whether you’re stopping in for a tasting, there’s always a reason to stay a little longer.
Upcoming Events
Live Music with Dan Cronin
April 18, 2026
Known as Panhandle Dan, a fingerpickin’ enthusiast with a lively, roots-inspired style. Free to attend.
Empanadas and Wine Pairing
April 25, 2026
Ticketed Pairing event with Sexi Mexi’s Empanadas and JCW Wines.
Mother’s Day Cheesecake Pairing
May 9, 2026
Ft. gourmet cheesecake from Cheesecake Bean, a sweet way to celebrate Mom.
Select From
Our Offerings
James Charles Winery & Vineyard produces award-winning Virginia wines recognized for quality and craftsmanship, with top-rated favorites available to taste at the winery or shop online.
2022 Bogaty Reserve Trinity
2022 Cabernet Sauvignon
2022 JC SS Chardonnay
James Charles Winery—Where Wine is Just the Beginning.
Our winemaker has earned 101 Wine Enthusiast ratings of 85 points or higher across our family of wines, reflecting a long-standing commitment to quality and craftsmanship. Explore our award-winning wines online or visit for a tasting.
Join the Legacy
Single
Membership: Perfect for solo sippers
- Get 3 bottles each quarter for $64 + tax (shipping optional) plus complimentary tastings, Club Room access (member + 1 guest), and 20% off wine, merchandise, and select events. Includes priority access to limited wines and 500 Loyalty Points.
Dual/Family
Membership: Best for couples and shared pours
- Share the perks: 3 bottles each quarter for $79 + tax (shipping optional) with complimentary tastings for both members, Club Room access (both members + 2 guests), and 20% off wine, merchandise, and select events. Includes priority access to limited wines and 500 Loyalty Points.
States We Ship To
AZ, AR, CO, FL, GA, HI, ID, IL, IN, IA, KS, KY, LA, ME, MD, MA, MN, MO, NE, NV, NH, NM, NY, NC, ND, OH, OK, OR, PA, SC, TN, TX, VT, VA, WA, WV, WI, WY, DC
Stay & Play Near James Charles Winery
Turn your visit to James Charles Winery into a perfect getaway! Whether you’re planning a relaxing retreat or looking for an adventurous exploration, Winchester and the Shenandoah Valley offer many nearby lodging options. They guarantee your stay is as memorable as your time with us.
FAQs
Q: Do I need a reservation at James Charles Winery?
A: Walk-ins are welcome unless a special event, private experience, or reservation-only offering says otherwise.
Q: Are dogs allowed?
A: Yes. Dogs are welcome inside the tasting room and outside at James Charles Winery. Please keep them leashed and attended at all times.
Q: Can I bring outside food or alcohol?
A: No. Outside food and outside alcohol are not permitted.
Q: Does James Charles Winery host live music and events?
A: Yes. James Charles Winery hosts live music, seasonal events, and ticketed experiences throughout the year.
Q: Can I book a group visit or private event?
A: Yes. Group visits and private events are available. Contact us directly for details.
Q: Does James Charles Winery have a wine club?
A: Yes. The James Charles Winery wine club includes member perks such as discounts and special access. Membership is a one-year commitment.
Q: Can I buy James Charles Winery wine online?
A: Yes. Available wines can be purchased online for pickup or shipping where permitted.