Stargazing, Polo & a Spooky Wine Walk.
Halloween comes a week early to wine country. Saturday night the UVA astronomers set up their telescopes in the orchard at Albemarle CiderWorks, and over in Keswick, Southwest Mountains sends you down a lantern-lit path with four wine stops and a few frights along the way. Sunday is Poloween, the costumed finale of the King Family polo season. In between: Scooby-Doo at Bold Rock, a chili cook-off in Scottsville, reggae at Glass House, and a homecoming show from Mariana Bell. Here’s your guide to 13 events across 12 venues in Charlottesville wine country.
Featured This Weekend
2026 Central Virginia Star Party — North Garden
Saturday, October 24 · 6:30 – 10:00 PM · Albemarle CiderWorks
CiderWorks’ annual Star Party hands the orchard over to the UVA Astronomy Department and its outreach program, Dark Skies, Bright Kids. Celestron, Dobsonian and UniStellar telescopes go up on the lawn, there’s a portable planetarium and hands-on astronomy for the kids, and cider tastings for the grown-ups. It’s free and open to all ages. North Garden is dark enough, once the sun drops behind the ridge, that you’ll see more than you expect — bring a warm layer and a blanket, and give your eyes twenty minutes to adjust.
Poloween: Halloween Sunday Polo — Crozet
Sunday, October 25 · 10:00 AM – 4:00 PM · King Family Vineyards
King Family closes its 2026 polo season the only way it could: in costume. There are costume contests for kids, for groups, and for dogs and other pets, plus trunk-or-treating along the tailgate row for anyone who wants to join in. The best-dressed tailgate wins a reserved tent space at a 2027 regular-season match, so expect people to go all out. Pack a picnic, pick up a bottle of Meritage at the tasting room, and settle in on the field’s edge under the Blue Ridge.
Friday — October 23
An acoustic evening in Crozet, a Friday Cheers set, and Scooby-Doo at the cidery.
Miles Pearce Duo — Fallen Tree Vineyard, Crozet · 4:30 – 7:30 PM
The Miles Pearce Duo mixes jazz, folk, Americana and Latin rhythms into an easy acoustic evening set. Fallen Tree is one of the smaller tasting rooms out in Crozet, which suits this kind of music: grab a glass, find a seat near the players, and let the week go.
Friday Cheers with Jacob Paul Allen — Blue Mountain Barrel House, Arrington · 5:30 – 8:30 PM
Jacob Paul Allen plays the Friday Cheers slot at the Barrel House, with the kitchen running its fried seafood specials. The music starts at 5:30, so you can make it down Route 29 before dark.
Ciders & Screams Movie Night: Scooby-Doo — Bold Rock, Nellysford · 7:00 – 9:30 PM
Bold Rock’s Friday spooky-movie series lands on Scooby-Doo this week, a safe pick for the whole family. Entry is free, and there are themed cocktails and dessert treats during the show.
Saturday — October 24
Wine and design in Gordonsville, classic rock under the tent, chili in Scottsville, and a haunted path after dark.
Wine & Design with Monica Garrett Interiors — Horton Vineyards, Gordonsville · 11:00 AM – 4:30 PM
Horton pours its award-winning wines while Monica Garrett Interiors sets up styled autumn vignettes in the tasting room. Hors d’oeuvres are provided. It’s free to attend, but space is limited and Horton asks you to RSVP.
Five Old Gentlemen (FOG) Live — Blenheim Vineyards, Charlottesville · 3:00 – 5:00 PM
FOG covers classic rock from the ’50s through the ’90s under the tent overlooking Blenheim’s vineyard. Admission is free and you don’t need a reservation. Buy a bottle and stay for the late-afternoon light.
4th Annual Chili Cook Off — James River Brewery, Scottsville · 3:00 – 6:00 PM
Scottsville’s brewery hosts its fourth chili cook-off, with live music from Old Hank and the 10-4 Good Buddies, Mr. Z’s BBQ on the food truck, and raffles and prizes. A $5 ticket gets you in. The drive down along the James is a good one this time of year.
Hallowine’s Spooky Wine Walk — Southwest Mountains Vineyards, Keswick · 7:15 – 9:30 PM
After dark, Southwest Mountains turns its property into a haunted path with four wine stops along the way. Tickets are $32 plus tax through Tock, and the vineyard warns that this is not just a casual stroll. Earlier in the day, the free Hallowine festival has apple bobbing and family activities.
Sunday — October 25
A sound bath, reggae at Glass House, a homecoming show, and a two-winery dinner to close it out.
Fall Sound Bath — Oakencroft Farm & Winery, Charlottesville · 10:30 – 11:30 AM
An hour of crystal singing bowls, light stretching and meditation in the Center at Oakencroft. Tickets are $34. Afterward the farm, a few minutes from Barracks Road, is a calm place to walk the pastures before the rest of your Sunday.
Sunday FunDay with Greg Ward — Glass House Winery, Free Union · 2:00 – 5:00 PM
Greg Ward is back at Glass House with an afternoon of reggae. There’s no cover and seating is first come, inside the conservatory or out. Picnics, kids and leashed, well-behaved dogs are welcome; outside alcohol isn’t.
Homecoming: An Evening with Mariana Bell — Southwest Mountains Vineyards, Keswick · 6:00 – 9:00 PM
The Front Porch, Charlottesville’s roots-music school, brings singer-songwriter Mariana Bell and her band home for an evening show, and the vineyard stays open late for it. Tickets are sold through Afton Tickets.
Early Mountain × Barboursville Vineyards — Early Mountain Vineyards, Madison · 6:00 PM
Two of Virginia’s best-known wineries share one table: a collaborative wine dinner pairing Early Mountain and Barboursville. Seats are booked through Early Mountain on Tock. It’s a fine way to end the weekend.