Improv in the Vineyard, Lobster Rolls & Sunflower Season
High summer delivers this weekend: Big Blue Door brings longform improv comedy to the deck at Cardinal Point, C-VILLE Restaurant Week makes its final pass through Early Mountain, and the sunflower fields at Chiswell hit peak bloom. Add a lobster festival, Christmas in July, and a Sunday of flowers and easy tunes — here's your guide to 50 events across 25 venues in Charlottesville wine country.
Featured This Weekend
Summer Harold Run! Big Blue Door Improv Comedy
Cardinal Point Winery — Afton · Saturday, July 25 · 6:30 PM · $10
Charlottesville's Big Blue Door troupe heads for the hills of Afton with two brand-new summer teams — Cork Royale and One Per Customer — each performing a "Harold," the original longform improv form where a single suggestion from the audience spins into a full set of interwoven scenes. No two shows are ever the same, and at ten bucks a ticket with Cardinal Point's wines flowing, it's the best cheap date in wine country this weekend.
Saturday evening: Two improv teams, one suggestion each, zero scripts — comedy under the Blue Ridge at Cardinal Point. Get event details →
Friday — July 24
Restaurant Week's last call & sunflowers at golden hour
C-VILLE Restaurant Week — Early Mountain Vineyards, Madison · Through Sunday, July 26
C-VILLE Restaurant Week is in its final stretch, and Early Mountain's kitchen — one of the best winery kitchens in the state — is on the list. It's the rare chance to settle into that soaring tasting room for a special Restaurant Week menu paired with their acclaimed Virginia wines. The week wraps Sunday, so make this your dinner move before it's gone. Get details →
Virginia Sunflower Fest — Chiswell Farm & Winery, Greenwood · Fri–Sun · 10:00 AM – 6:00 PM
The sunflower fields at Chiswell are in full golden riot, framed by Blue Ridge views in every direction. Wander the rows, pick your own stems, and cool off with a glass of Chiswell wine while food trucks and live music round out the afternoon. Runs all three days — mornings are quietest, golden hour is prettiest. Get details →
America 250 Series: An Evening with Fred Reno — Pollak Vineyards, Greenwood · 6:00 PM – 8:00 PM
Pollak's America 250 series continues with an evening tasting alongside Fred Reno, a longtime voice in the Virginia wine world. Expect good pours, better stories, and a lakeside Greenwood setting that does its best work right around sunset. Get details →
Veritas Supper Series — Southern Roots — Veritas Vineyard & Winery, Afton · 6:30 PM – 10:00 PM · $100
Veritas sets the long table for Southern Roots, a seasonal supper celebrating the flavors of the American South at the height of summer — classic Southern cooking, regional ingredients, and a toast to America's 250th. $100 includes wine pairings and service; wine club members take 20% off their first two tickets. Get details →
Saturday — July 25
Lobster rolls, Christmas in July & a Saturday night special
4th Annual Lobster Festival with Salty Bottom Blue Oysters — Keswick Vineyards, Keswick · 12:00 PM – 5:00 PM
New England comes to the Keswick courtyard: Salty Bottom Blue Oysters shucks and stacks its way through the 4th Annual Lobster Festival, with lobster rolls and fresh oysters paired against Keswick's whites and rosés in the open air. Coastal feast, vineyard views — wear the bib proudly. Get details →
Christmas In July Concert with Tropical Attitudes — DuCard Vineyards, Etlan · 2:00 PM – 5:00 PM · No Cover
DuCard decks the halls in the middle of summer: Tropical Attitudes brings its Jimmy Buffett–style tropical rock and country to the mountains, with Christmas-themed surprises and a visit from Santa himself. Dress code: your loudest Hawaiian shirt. No cover; reservations recommended. Get details →
Saturday Night Special: Tyler Dick Band — Chisholm Vineyards at Adventure Farm, Earlysville · 6:00 PM – 9:00 PM
Chisholm keeps the lights on late for its Saturday Night Special, with the Tyler Dick Band plugging in for a full evening set on the farm. Bring a crew and a lawn chair, grab a bottle of estate wine, and let the band carry you into Saturday night. Get details →
Sunday — July 26
Fresh flowers, harmonica blues & a slow Sunday finish
Blooms 4 Good Floral Workshop — Southwest Mountains Vineyards, Keswick · 1:00 PM – 5:00 PM
Spend your Sunday afternoon elbow-deep in summer blooms: Blooms 4 Good joins Southwest Mountains Vineyards for a hands-on floral workshop in one of the area's most beautiful new tasting rooms. Build your own arrangement, sip something cold while you work, and walk out with the best-looking souvenir of the weekend. Get details →
John Kelly & Gary Green — Glass House Winery, Free Union · 2:00 PM – 5:00 PM · No Cover
Singer-songwriter John Kelly on guitar and vocals, joined by harmonica wizard Gary Green — a Sunday afternoon of soulful, unhurried music among the banana trees of the Glass House conservatory. Open to all, no cover. Get details →
Sue Harlow Music — Hark Vineyards, Earlysville · 3:00 PM – 6:00 PM
Close out the weekend on the Hark patio with Sue Harlow's easygoing acoustic set, a glass of estate wine, and vineyard rows rolling off toward the mountains. The gentlest possible landing before Monday. Get details →
Browse all events at weekendr.info.