Seasonal & Holiday Events in Charlottesville Wine Country

Witches' Day Out

Gather your coven for a witch-themed Halloween celebration and costume contest on Sunday, 10/25, supporting Crozet Cares Closet.

Halloween at Eastwood 🎃

Celebrate Halloween at Eastwood with a fun afternoon for the whole family! Join us on Saturday, October 31 from 12–4 PM for live music, Halloween treats, kids’ activities, and plenty of festive fun. Kids are invited to come dressed in their favorite costumes for our costume parade and prizes, while parents can enjoy a glass of wine, cider, or beer and a bite to eat.

Eastwood After Dark: Halloween Edition 👻

Halloween is taking over Eastwood! Put on your best costume and join us for an evening of swing dancing, live music, wine, and Halloween fun. Swing Cville will kick things off with a swing dance lesson at 4 PM, followed by live music from Zuzu’s Hot 5 from 5–8 PM. Costumes are highly encouraged! Show off your Halloween spirit in our costume contest, with prizes for the best looks.

Veritas Illuminated Walking Light Trail

The fifth annual Veritas Illuminated, a dazzling holiday walking light trail winding through the grove and vines of Veritas Vineyards and Winery. Open select dates November 25 - December 26, 2026; check the Veritas website for nightly hours and tickets. Veritas Wine Club Members receive the first four tickets free.

Mini Maker’s Holiday Market

Eastwood Farm and Winery is hosting our first-ever Young Makers Market on Saturday, November 28 — featuring kid and teen artisan vendors selling handmade goods just in time for the holidays!

Oktoberfest at Brewing Tree

Oktoberfest at Brewing Tree

Crown Club Saturday: Grape Stomp

Crown Club members take a pre-harvest look at the crop before engaging in some old-fashioned grape stomping! 6:30pm-8:30pm.