An Oyster Roast and a Square Dance.
Second weekend of October, and the fall calendar stops being polite about it. Keswick shucks Chesapeake oysters on the lawn all Sunday afternoon, Chiswell sits Gearharts truffles down next to a flight on Saturday night, and Potter's hands the floor over to a stringband and somebody willing to teach you the steps. In between: trivia in Crozet, a cookie class in a vineyard kitchen, and a harvest dinner in Palmyra. Here's your guide to 13 events across 13 venues in Charlottesville wine country.
Featured This Weekend
Fall Oyster Roast with Salty Bottom Blue — Keswick
Sunday, October 11 · 12:00 – 5:00 PM · 1575 Keswick Winery Dr.
Salty Bottom Blue brings its oysters up from the Chesapeake and sets up on the lawn at Keswick for five hours on Sunday — raw on the half shell, roasted over fire, and the usual accompaniments. Keswick's Viognier is built for exactly this, which is rather the point. The lawn at Keswick in the second week of October is one of the better places in the county to spend an afternoon doing nothing in particular. Come when it opens if you want the raw bar at its freshest; come at three if you'd rather have the light.
Chocolate & Wine with Gearharts — Greenwood
Saturday, October 10 · 6:00 – 8:00 PM · Chiswell Farm & Winery
Gearharts is Charlottesville's own chocolatier, and this is the pairing it does best: a guided flight at Chiswell with a truffle chosen for each pour. Done properly, a single-origin dark against a big red is one of the few pairings that genuinely improves both halves. Chiswell sits on the Chiles family orchard land at Greenwood, which makes the drive out Route 250 worth leaving early for. Two hours, seated, and small enough that you'll want to book.
Friday — October 9
A movie under the stars, a new trivia night, and a square dance in an old church.
Dinner & a Movie Night — Southwest Mountains Vineyards, Keswick · 6:30 – 10:30 PM
Supper first, then a film on the lawn with the Southwest Mountains behind the screen. October evenings in Keswick get cool once the sun drops behind the ridge, so the blanket is not optional — but a glass of estate red and a projector under the stars is a hard combination to beat this time of year.
'Wine Down' Trivia Night — Grace Estate Winery, Crozet · 6:00 – 8:00 PM
Grace Estate's new Friday trivia night, two hours of it, on a property at the foot of the Blue Ridge with the vines running up the slope behind you. Bring a team or borrow one. The barn stays warm, which by the second week of October starts to matter.
Night Moves: Bob Seger Tribute — Basic City Beer Co., Waynesboro · 7:30 PM
A full Seger tribute in the old Virginia Metalcrafters plant on East Main in Waynesboro — a brick-and-steel room that does loud, warm rock better than most purpose-built venues. Forty minutes over Afton from Charlottesville, and worth it for "Turn the Page" alone.
Boot Scoot Square Dance Party — Potter's Craft Cider, Charlottesville · 5:30 PM
Old-time stringband music from Big Silch and dances taught by Hannah Johnson, which is the part that matters: nobody expects you to already know how. The old church that Potter's turned into a cidery has the right floor and the right ceiling for it, and a pint of Farmhouse Dry between sets is the correct move.
Saturday — October 10
A cookie class, an easel, a farm stage, and a general store with a back room.
Kooking with Kam — Fallen Tree Vineyard, Crozet · 11:00 AM
Kam runs a hands-on session in the vineyard kitchen at Fallen Tree, one of the newer places out Clark Road in Crozet and still small enough that a cooking class actually feels like a cooking class. You leave having made something and having drunk something, which is the right ratio for a Saturday morning.
Paint + Sip — 92 Acres, Charlottesville · 12:30 – 2:30 PM
Blue Ridge Brushes runs the easels; 92 Acres supplies the glass and the view. This is one of the newest tasting rooms in the county — out Taylors Gap Road, barely fifteen minutes from town but entirely in the country — and two hours with a brush is a reasonable excuse to go see it.
Bailey Hayes — Bald Top Brewing Co., Madison · 6:00 – 9:00 PM
Three hours of Bailey Hayes on the farm at Bald Top, up Thrift Road in Madison County with the mountains filling the whole western side of the view. The drive up 29 at golden hour in October is half the reason to go; the other half is that Bald Top's lawn empties out slowly and nobody hurries you.
JD Morrow — The Batesville Market, Batesville · 7:00 – 9:00 PM
The Batesville Market is a general store with a stage in the back and not many seats, which means a JD Morrow set there is about as close as live music gets around here. Tickets through Afton Tickets in advance — the room sells out more often than its size suggests.
Sunday — October 11
A library flight, an Irish session, and a harvest dinner to close it out.
Smuggler Sunday: Library Wines Flight — Pollak Vineyards, Greenwood · 11:00 AM · Wine club members
Four vintages of Pollak's 100% estate-grown Meritage, poured side by side — the sort of vertical that tells you more about a site in twenty minutes than a year of single-bottle tastings will. Wine club members only, which is the trade-off; if you are one, this is the best thing on the calendar all weekend.
Aaron Olwell & Friends Irish Music — Albemarle CiderWorks, North Garden · 2:30 – 4:30 PM
Aaron Olwell comes from a family that has been making wooden flutes in Nelson County for decades, and the session he brings to Albemarle CiderWorks is the real article — tunes passed around a circle rather than a set list. It runs the second Sunday of every month, and two hours of it with a glass of cider is a quietly excellent way to end a weekend.
Harvest Wine Dinner with Chef Andy — Cunningham Creek Winery, Palmyra · 6:00 – 9:00 PM
A multi-course sit-down with Chef Andy to close out the harvest: pumpkin chili, applewood-smoked pork loin, sweet potato, each course poured against a Cunningham Creek wine. Three hours, properly seated, twenty-five minutes southeast of town — the kind of Sunday dinner that makes Monday feel further away. Reserve ahead.