Welcome to Weekendr
One directory for everything happening in Charlottesville wine country: live music, tastings, festivals, food trucks, and events at wineries, breweries, and cideries across the Monticello AVA.
The Weekendr Blog
Guides, winery spotlights, and weekend picks.
Cville Weekendr — July 10–12, 2026
A lobster feast, a charity casino night, a Led Zeppelin tribute, and tomato-season supper clubs — your guide to 40 events across 22 venues in Charlottesville wine country.
Cville Weekendr — June 26–28, 2026
Monticello Wine Week in full swing — the Gold Medal Celebration and Rosé Festival, plus Final Fridays at Pollak, a summer boil, and Sunday polo. 41 events across 25 venues.
Cville Weekendr — June 19–21, 2026
Juneteenth on Friday, the summer solstice on Saturday, Father’s Day on Sunday — and Hazy Mountain turning five in between. The weekend across 63 venues in Charlottesville wine country.
Cville Weekendr — May 29–31, 2026
Oysters on Friday, classic rock in the mountains on Saturday, and polo on the lawn Sunday morning — it’s a good one. 92 events across 62 venues in Charlottesville wine country.
Cville Weekendr — May 22–24, 2026
Memorial Day weekend is here — from sea shanties at Potter’s Craft to polo ponies at King Family, Charlottesville wine country is throwing a proper party.
Cville Weekendr — May 8–10, 2026
Square dancing, winemaker dinners, rosé all day, and a Pearl Jam tribute — plus the best places to take Mom for Mother’s Day weekend in Virginia wine country.
Cville Weekendr — May 1–3, 2026
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.
Cville Weekendr — April 24–26, 2026
Live music at Pollak, a spring wine dinner at Pippin Hill, Sunday afternoon at Eastwood Farm, and a spotlight on the highest-rated winery in the region. Your weekend, picked.
Cville Weekendr — April 17–19, 2026
A packed weekend ahead — grand tastings, mountain views, square dancing, and jazz in the orchard. Here’s what’s worth the drive.