James Charles Winery Tree Lighting in Winchester: Dec. 5

James Charles Winery & Vineyard lights its Christmas tree at its Tree Lighting Festivity, 6 to 9 p.m. Saturday, Dec. 5, at the winery, 4063 Middle Road, southwest of Winchester. Admission is free, and the evening includes a visit from Santa, live alpacas, free hot cocoa, local vendors and live Christmas music.

Last checked 2026-11-11.

Upcoming dates

• Sat. Dec. 5, 6 to 9 p.m.

The winery lists one evening for the 2026 tree lighting; the organizer lists dates through Dec. 5. Its events page carries the rest of its holiday calendar.

What’s planned

The winery’s event page lists:

• The tree lighting, with live Christmas music through the evening.
• Santa Claus, who is stopping by so children can sit on his lap and share their Christmas wishes.
• Live Christmas alpacas for guests to meet up close.
• Complimentary hot cocoa.
• Holiday shopping with local vendors selling gifts and handmade goods.

The winery bills it as a family evening and invites guests to bring their friends.

Where it is and parking

James Charles Winery & Vineyard is at 4063 Middle Road, Winchester, in Frederick County southwest of the city. The winery’s phone number is 540-931-4386.

The winery does not publish parking arrangements for the tree lighting on its event page. Its policies page recommends planning transportation in advance and says the winery is usually Uber- and Lyft-friendly, though availability varies; if you book a ride, confirm the driver has the right address and knows the entrance. Groups arriving by bus or shuttle should coordinate with their transportation company.

Tickets and cost

• Admission: free, the winery says. No tickets are listed.
• Hot cocoa: complimentary.
• Wine, food and vendors’ goods: sold separately. The winery serves its own wines and a seasonal menu of small plates, flatbreads and charcuterie boards.

What to know

These come from the winery’s policies page:

• Kids: families are welcome. Children must be supervised at all times and stay with their group.
• Dogs: leashed, well-behaved dogs are welcome on the patio, in the outdoor spaces and inside the tasting room. Owners must clean up after them, and a disruptive dog may be asked to step outside.
• No outside food or alcohol. Outside alcohol, including wine from other wineries, beer, cider and liquor, is prohibited under Virginia ABC rules and will be confiscated. Only James Charles wines may be consumed on the property.
• Coolers are allowed, but staff may inspect them.

For the city’s own parade and tree lighting in Old Town on Monday, Nov. 30, see our Christmas parade and tree lighting page; more lights, Santa visits and December outings are in our holiday lights and Christmas events guide, and other places that welcome pets are in our dog-friendly guide.

Dates and venues as listed on the Winchester-Frederick County Convention & Visitors Bureau calendar and confirmed on the organizer’s site.

Frequently asked questions

When is the tree lighting at James Charles Winery?

Saturday, Dec. 5, 2026, from 6 to 9 p.m. at James Charles Winery & Vineyard, 4063 Middle Road, Winchester.

Is the James Charles Winery tree lighting free?

Yes. The winery says admission is free, and hot cocoa is complimentary. Wine, food and vendors’ goods are paid for separately.

Will Santa be at the James Charles Winery tree lighting?

Yes. The winery says Santa Claus will visit, and children can sit on his lap and tell him their Christmas wishes. Live Christmas alpacas will also be there.

Can I bring my dog to James Charles Winery?

The winery’s policy welcomes leashed, well-behaved dogs on the patio, in its outdoor spaces and inside the tasting room.

Can I bring my own food or wine?

No. The winery does not allow outside food, and outside alcohol is prohibited under Virginia ABC rules. Only James Charles wines may be consumed on the property.