Your Weekend in Wine Country
Memorial Day weekend is here — and Charlottesville wine country is throwing a proper party. From sea shanties at Potter’s Craft to polo ponies at King Family, there’s something worth getting off the couch for. Here’s your guide to the weekend.
Venue Spotlight: King Family Vineyards
Crozet, VA · Est. 1998 · kingfamilyvineyards.com
Perched on the eastern face of the Blue Ridge near Crozet, King Family Vineyards has spent nearly three decades building a reputation for Bordeaux-style reds and a weekend culture that’s genuinely hard to beat. The estate’s Meritage and Cabernet Franc consistently earn national recognition — but on Sundays in polo season, the wines share the spotlight.
This Memorial Day marks the official opening of King Family’s 2026 polo season. The annual kickoff draws a full house — families on blankets, riders warming up the ponies, and the mountain ridge doing its thing in the background. It’s the kind of afternoon that defines what a Charlottesville Sunday should feel like.
This Sunday: Polo Season Opener — free admission, food trucks on site, wine by the glass. 11am–5:30pm. See full events calendar →
Friday
Kick off the long weekend
Late Friday + Live Music with Shane Click — Valley Road Vineyards · 5:00 PM
There is no better way to kick off a holiday weekend than with Late Friday at Valley Road Vineyards — live music, great wine, and a crowd that’s ready to celebrate. Get details →
Matthew O’Donnell Live — Potter’s Craft Cider · 5:30 PM
A modern energy to traditional drinking songs, sea shanties, Irish jigs & reels, and timeless folk favorites. A proper send-off into the long weekend. Get details →
Saturday
Find your spot
Waves of Flavor — Memorial Day Seafood Weekend — Keswick Vineyards · 11:00 AM – 5:00 PM
Try Fabulous Foods returns to Keswick for two days only — an incredible seafood food truck event paired with Keswick wines. The unofficial start of summer, right here. Get details →
Guest Star Hike Experience — Southwest Mountains Vineyards · 12:00 PM – 2:00 PM
Join Jeremy, the assistant winemaker, for a one-of-a-kind hiking experience. Enjoy the outdoors while getting an inside look at the craft behind the wines. Get details →
The Wavelength Trio with Lisa Carter — Glass House Winery · 5:00 PM – 7:30 PM
Join us in the tropics for The Wavelength Trio with special guest Lisa Carter — known for her evocative, soulful vocals. Expect surprising rock covers, blues and classics. Open to all, no cover. Get details →
Sunday
Memorial Day Sunday
Polo Season Opener — Memorial Day Sunday — King Family Vineyards · 11:00 AM – 5:30 PM · Free Admission
The 2026 polo season officially kicks off on Memorial Day Sunday. Whether you’re a polo enthusiast or just discovering the sport, this is a great day out. Food trucks on site. Free admission. Get details →
Sunday Brunch — Hazy Mountain Vineyards · 11:00 AM – 3:00 PM
Indulge in a thoughtfully curated brunch menu, sip on a refreshing mimosa, and take in breathtaking mountain views. The perfect slow start to a long holiday Sunday. Get details →
See all weekend events at weekendr.info.