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Cville Weekendr — August 21–23, 2026

· Weekendr Editorial

A Square Dance, a Peach Orchard & Starry Nights

Veraison is well under way, the fruit is going purple on the vine, and the last full weekend of August has turned into one of the busiest of the season. Potter's clears the floor for an old-time square dance Friday, Grelen opens the orchard for a peach-tree walk at nine on Saturday morning, Veritas runs Starry Nights until eleven, and Glass House keeps its tropical conservatory humming all three days. Here's your guide to 53 events across 27 venues in Charlottesville wine country.

Featured This Weekend

Glass House Winery & Brewery — Free Union

Glass House Winery in Free Union

5898 Free Union Road · Fri 12–9, Sat 12–8, Sun 12–5:30

Twenty minutes northwest of town, past the last of the pavement, there is a glass conservatory full of banana trees. That is not a metaphor. Glass House has been growing its own fruit and making its own wine in Free Union since 2006, and somewhere along the way it added a brewery, a chocolatier and a bed and breakfast — so a Saturday here can start as a tasting and end as a weekend away. The tropical room is the reason people first come out; the estate wines, the handmade chocolates and the fact that nobody minds your dog are why they keep coming.

This weekend they run music all three days, and none of it costs a dime at the door:

All three shows are free. No cover, no reservation.

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Friday — August 21

Swing your partner, then pour something cold.

Boot Scoot Square Dance Party — Potter's Craft Cider, Charlottesville · 5:30 PM

Boot Scoot Square Dance Party at Potter's Craft Cider

A live string band, a caller, and a room full of people who mostly have no idea what they are doing — which is the entire point. Hannah Johnson teaches every dance from the floor, so showing up alone and knowing nothing is the standard way to arrive. Potter's old church on Rio Road has the wooden floor and the ceiling height this deserves, and there is cider at the bar when your legs give out.

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Music on the Lawn: Bob & Kenn — Jefferson Vineyards, Charlottesville · 5:00 – 7:00 PM

Friends toasting with wine glasses at Jefferson Vineyards

Two hours of easy guitar-and-harmony on the lawn at Jefferson Vineyards, on ground Thomas Jefferson picked out for grapes in 1774 and that took another two centuries to get right. Estate wines by the glass or the bottle, tables under the trees, and Monticello up the hill behind you. Free, and about as close to town as wine country gets.

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Music Bingo at Grace Estate — Grace Estate Winery, Crozet · 6:30 – 8:30 PM

Music Bingo at Grace Estate Winery

Bingo, except the numbers are songs and everyone at your table suddenly has opinions about the 1990s. Tag Team Entertainment runs it, Grace Estate pours it, and the whole thing plays out on a lawn that looks straight into the Blue Ridge as the sun goes down. Bring four people and a competitive streak.

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Saturday — August 22

Peaches at nine, honky-tonk at seven, stars until eleven.

Starry Nights at Veritas: Hipshack — Veritas Vineyard & Winery, Afton · Gates 5:30 PM, music 7–11 PM

Starry Nights at Veritas Vineyard & Winery

Veritas's signature summer night: gates at 5:30, blankets and low chairs staking out the slope below the winery, dinner from the grill, and Hipshack playing until eleven with the Blue Ridge going dark behind the stage. It is the one Afton evening that regulars plan the rest of their August around. Tickets are required and it does sell out — check availability before you drive.

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The Grelen Orchard: Peach Trees — The Market at Grelen, Somerset · 9:00 AM, free

The Grelen orchard pick-your-own sign

Grelen's garden staff walk you through the orchard at the best hour of the day and explain what it actually takes to keep a peach tree productive in central Virginia — pruning, thinning, the pests, the frost math. Free, an hour or so, and the sort of thing that changes how you look at your own back yard. RSVP is recommended; the Market and the pick-your-own open right after.

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Leroy Burks & The Voodoo Whiskey Band — Pro Re Nata Brewpub, Crozet · 7:00 – 10:00 PM

Leroy Burks and the Voodoo Whiskey Band at Pro Re Nata

Three hours of unapologetic honky-tonk — the '90s country you know every word to, plus enough of the current stuff to keep the younger half of the room happy. PRN has the taps, Hops Kitchen out back, fire pits and a stage built for exactly this. Free show, and the parking lot fills early when a country band is on the board.

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Sunday — August 23

Sangria, a deck, and one last long afternoon.

Sangria Summer Market — Eastwood Farm and Winery, Charlottesville · 12:00 – 5:00 PM

Sangria Summer Market at Eastwood Farm and Winery

Five hours of local makers set up across the Eastwood grounds, with a glass of their summer sangria in your other hand. It is the last market of the season before the calendar turns to harvest, so expect the good vendors and a decent crowd. Eastwood sits five minutes past Pantops and feels an hour further out.

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Music on the Deck: Jimmy O — Cardinal Point Winery, Afton · 2:00 – 5:00 PM

Jimmy O playing guitar at Cardinal Point Winery

Cardinal Point's deck faces straight at the mountains, and Jimmy O has the three-hour Sunday set down to an art — enough familiar songs to sing along to, played quietly enough that nobody has to stop talking. Bring a picnic if you like; the winery is happy for you to.

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Sunday Session: The Michael Elswick Gathering — Chisholm Vineyards at Adventure Farm, Earlysville · 1:00 – 4:00 PM

The Michael Elswick Gathering playing at Chisholm Vineyards

The Gathering is a full band — horns and all — which is more than most Sunday afternoons get, and Chisholm's hillside carries it well. Pastures on one side, vines on the other, room for everyone to spread out. A good place to let the weekend run out slowly.

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Browse all events at weekendr.info.