
Summer's Last Long Weekend
Three days to spend it properly. Three chefs go head-to-head in a Caribbean cook-off at Albemarle CiderWorks, Bald Top closes Saturday with fireworks over the farm, and Blenheim puts Dave Matthews Band on a big screen under the tent. Oysters Friday, a Buffett tribute Sunday, and one gloriously silent book club in between. Here's your guide to 15 events across 13 venues in Charlottesville wine country.
Featured This Weekend
Caribbean Cook-Off — Albemarle CiderWorks, North Garden
Saturday, September 5 · 12:00 – 4:30 PM

Three local chefs cook against each other in the orchard, and you get to eat the evidence. Buy a wristband and taste your way through the field — jerk, griot, pikliz, whatever they bring — while Byron Massie plays noon to two and the Lua Project takes it from 2:30 to close. Every dollar goes to the Ford Haitian Foundation, which makes this the rare afternoon where a second helping counts as charity. Come hungry, vote with your fork, and stay for the Lua Project.
Friday — September 4
Oysters, the Currys, and Dave on the big screen.
The Currys with Carries Soul Food Truck — Glass House Winery, Free Union · 6:00 – 8:30 PM

The Currys have been folding rock, Americana and country into tight sibling harmonies for years now, and they are hard to beat on a warm evening in the Glass House courtyard. Carries Soul brings the food truck, so dinner is handled. No cover, open to all — just show up.
Labor Dave Weekend: DMB on the Big Screen — Blenheim Vineyards, Charlottesville · 7:00 PM · $35
Dave Matthews Band on a big screen, under the tent, at the winery Dave himself owns. It is about as Charlottesville as a Friday night gets. Tickets are $35 and the room is small, so this one goes early.
Virginia Oyster & Wine with Live Music: FarAway — Eastwood Farm and Winery, Charlottesville · 5:00 – 8:00 PM

Eastwood shucks Virginia oysters every Friday evening and pours the wine to go with them. FarAway plays 5 to 8. No reservations needed — find a table on the lawn and settle in.
End of Summer Seafood Shindig — Chiswell Farm & Winery, Crozet · 11:00 AM – 5:00 PM, Sep 4–7

Four days of fresh seafood and free live music at Chiswell, running Friday straight through Monday. Come Friday for the quietest crowd of the weekend, or pick your day — the wine and the mountain view do not change.
Saturday — September 5
Cook-off smoke, mountain music, fireworks after dark.
Labor Day Celebration at Bald Top Brewing — Bald Top Brewing Co., Madison · 2:00 – 9:00 PM · Free

Virginia's first historic farm brewery goes big for the holiday: S. River Strings play rock and bluegrass 2 to 5, Vertigo Down bring the Zeppelin-to-Sabbath end of things 6 to 9, and fireworks go up over the farm once the sun is down. Twenty taps, a scratch kitchen doing pizza and barbecue, a lawn that runs straight at the Blue Ridge, and dogs welcome. Back Sunday 2 to 5 with Little Walter and the Convictions.
Live Music: Brent Hull — Afton Mountain Vineyards, Afton · 2:00 – 5:00 PM

Brent Hull plays the afternoon slot at Afton Mountain, where the tasting room is open 11 to 7:30 and the view down the valley does half the work. An easy anchor for a Saturday that starts early and ends late.
Live Music: Matt Johnson — Keswick Vineyards, Keswick · 12:00 – 4:00 PM

The Voice alum and long-time local favorite Matt Johnson takes the Keswick lawn for four hours straight. Grab a bottle rather than a glass — you will be there a while.
Last Sips of Summer — Bold Rock Cidery, Nellysford · 11:00 AM – 8:00 PM

Bold Rock sends summer off with hot dog flights, bloody mary specials, cornhole and a bounce house for the kids. Lama and the Hound play 12 to 2:30. Nine hours of it, if you have the stamina.
Live Music: Alex Arbaugh — Brewing Tree Beer Company, Afton · 1:00 PM

Guitar-driven original rock with a Southern and Americana streak, played in the Brewing Tree beer garden. A good counterweight to a day otherwise spent in tasting rooms.
Sunday — September 6
Vinyl, a Buffett tribute, and a very quiet book club.
WTJU Vinyl Takeover + Prints, Platters, Pints & PRIDE — Potter's Craft Cider, Charlottesville · 1:00 PM

WTJU's DJs take over the turntables while a vendor market fills the yard with prints, records and local makers. Cider, art and PRIDE in one afternoon at the old church on Rio Road. Free to wander.
Music In The Mountains: Tropical Attitudes — DuCard Vineyards, Etlan · 2:00 – 5:00 PM

A Jimmy Buffett tribute on the anniversary of his death, played on DuCard's shaded patio with the mountain stream running below. Cold wine, warm afternoon, and a set list everyone already knows.
Long Live the Jam! — Starr Hill Brewery, Crozet · 2:00 – 5:00 PM

An open jam at the Crozet taproom — bring an instrument and sit in, or bring nothing and just listen. Either way the beer is good and the bar for participation is refreshingly low.
Silent Book Club — Albemarle CiderWorks, North Garden · 12:30 – 3:00 PM · Free

No assigned reading, no discussion questions, no obligations — bring whatever you are already reading and sit with other people doing the same. Cider optional but strongly implied. Free, first Sunday of every month.
Browse all events at weekendr.info.