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Cville Weekendr — May 1–3, 2026

· Weekendr Editorial

Fire Feasts, Derby Day & Mountain Music

Polo season kicks off with an Argentine asado on Friday, Kentucky Derby Day calls for wine and BBQ on Saturday, and a mountain singer-songwriter closes out the weekend Sunday. Here’s your pick.

Featured Events

2nd Annual Argentine Asado at King Family

Friday · Dinner & Music — King Family Vineyards, Crozet · Friday, May 1 · 6:00 PM – 8:30 PM · $85

The official kickoff of polo season at one of Virginia’s most iconic estate wineries. This open-fire Argentine feast — inspired by the asador culture at the heart of polo — pairs classic asado fare with a welcome glass of King Family wine, live music by the Will Gravatt Band, and the chance to meet the polo players themselves. A rare Friday night to remember. Wine club members save $10. Get tickets →

Derby Day Celebration at Woodbrook Farm Vineyard

Saturday · Derby Day — Woodbrook Farm Vineyard, Orange · Saturday, May 2 · 2:00 PM – 7:00 PM

This one’s perfectly poetic: Woodbrook Farm Vineyard sits on what was once a working thoroughbred racehorse training facility, and their tasting room is the old Training Barn. On Kentucky Derby Day, that history comes alive — live music from Austin Boggs, BBQ from Zippy’s food truck, and a widescreen Derby broadcast. Break out the derby hat and dress to impress at one of Orange County’s most charming hidden gems. View details →

Music in the Mountains: Annie Stokes at DuCard

Sunday · Live Music — DuCard Vineyards, Etlan · Sunday, May 3 · 2:00 PM – 5:00 PM

Close out the weekend the right way — sitting by the stream below Old Rag Mountain while Annie Stokes works through a set of classic rock, country, bluegrass, and folk. The Northern Virginia and Shenandoah Valley artist plays guitar, ukulele, and mandolin with the kind of easy warmth that makes three hours feel like thirty minutes. Open daily, no reservation needed, dogs welcome. View details →

Venue Spotlight: Worth the Drive

King Family Vineyards

6550 Roseland Farm, Crozet, VA · 15 minutes from Charlottesville · Winery · Polo · Outdoor Seating

King Family Vineyards is two things at once: one of Virginia’s most awarded estate wineries, and home to Roseland Polo — one of the most unique public polo experiences on the East Coast. The King family moved here from Houston in 1995 specifically because David had played polo since 1980 and needed twelve flat acres. What grew around that field is now a beloved destination in the Blue Ridge foothills. This Friday, they officially launch their polo season with the Argentine Asado — an open-fire feast rooted in polo culture. Free public polo matches return Memorial Day weekend and run every Sunday through October. Explore venue →

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See all weekend events at weekendr.info.