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Cville Weekendr — June 19–21, 2026

· Weekendr Editorial

The Longest Weekend of the Year

Juneteenth on Friday, the summer solstice on Saturday, Father’s Day on Sunday — and Hazy Mountain turning five in between. Here’s your guide to the weekend across 63 venues in Charlottesville wine country.

Venue Spotlight: Hazy Mountain Vineyards

Afton, VA · Est. 2021 · hazy-mountain.com

Hazy Mountain is a family-owned estate winery with 86 acres of vineyards tucked into the Blue Ridge, straddling both the Monticello and Shenandoah Valley AVAs. Perched off Route 151 in Afton, they’ve spent the last five years making wines that let the land do the talking — and this weekend, they turn five.

The anniversary festivities are in full swing this weekend. On Saturday, their Production Tour & Tasting (1pm) takes you behind the scenes, and the 5th Anniversary Gala Wine Dinner (6pm) brings a multi-course feast — filet mignon, lobster, and the best of the cellar. Sunday rounds it out with a Candle Making Workshop at 2pm.

This Saturday: 5th Anniversary Gala Wine Dinner — multi-course menu with filet mignon & lobster, paired with estate wines. 6:00 PM. See full events calendar →

Friday — June 19 — Juneteenth

Celebrate and raise a glass

Juneteenth Jubilee — Eastwood Farm and Winery · 12:00 PM

June 19th means something — head to Eastwood Farm and Winery for their Juneteenth Jubilee. A community celebration among the vines at one of the valley’s most beloved farm wineries. Good people, great wine, meaningful afternoon. Get details →

Friday Cheers with The Whiskey Shakes — Blue Mountain Brewery · 5:30 PM

Kick off the solstice weekend at Blue Mountain with The Whiskey Shakes — one of the longest evenings of the year, cold beer in hand, live music echoing off the mountains. Book your Friday night right here. Get details →

Saturday — June 20 — Summer Solstice

The longest day, perfectly spent

Live Music: So Diverse! — Afton Mountain Vineyards · 4:00 PM

Spend the summer solstice on the mountain with So Diverse! at Afton Mountain Vineyards. Their eclectic sound carries all the way across the hillside, and the Tasting House stays open late for the longest day of the year. Get details →

Summer Solstice Wine Dinner — Southwest Mountains Vineyards · 7:00 PM · Ticketed

The longest day of the year deserves the most memorable table. Southwest Mountains teams with Luce for an enchanting midsummer wine dinner under the stars — a true solstice celebration in the vineyard. Get details →

Sunday — June 21 — Father’s Day

Polo and good company

Roseland Polo — King Family Vineyards · 12:00 PM · Free Admission

Sunday polo at King Family — this week falling on Father’s Day. Pack a blanket, bring the crew, and watch world-class polo against the backdrop of the Blue Ridge. Free admission, tailgating welcome. Gates open 10am, matches at noon and 2pm. Get details →

Father’s Day Sunday Session — The Trio — Chisholm Vineyards · 1:00 PM

Treat Dad to a relaxed afternoon in the valley at Chisholm Vineyards. The Trio plays while the Catch the Chef food truck brings the food. The kind of Sunday Dad actually wants — good wine, great music, no fuss. Get details →

Browse all events at weekendr.info.