Chiswell Farm & Winery

06/15/2026

06/15/2026

Do you know your pop classics? Are you the person everyone trusts to make the Spotify playlist? You belong at Music Trivia Night this Thursday!

Starting at 5 PM on 6/18, host Rachael Karpo Entertainment’s music-themed questions are designed for all skill levels. As long as you like music, you’ll have a blast at this free event.

Learn more about our monthly Trivia & Tunes events at chilesfamilyorchards.com/calendar/tt-trivia-2026

06/12/2026

Our 2025 Viognier is turning heads… have you tried everyone’s new favorite white yet?

06/11/2026

Music Trivia Night with Rachael Karpo is next week! No need to study ahead, just show up at 5 PM on Thursday, 6/18, for three rounds of harmonies and hilarity.

06/07/2026

Crown Club members should register by tomorrow for our summer picnic dinner on Saturday, 6/13! Let's bond over fried chicken, mac & cheese, and Chiles Peach Orchard peach pies.

👑 Each member and up to one guest can attend for free — bring additional guests for $25 each. Call or email to RSVP by 6/8.

06/06/2026

👑 June’s Crown Club special is 50% off bottles of our most-awarded white wine, our 2021 Chardonnay!

Its delicate, sweetly tropical flavors emerged through slow malolactic fermentation in French oak barrels. We like to pair it with creamy, rich dishes like seafood chowder, risotto, or alfredo.

06/04/2026

Tomorrow’s Summer Sundown event features Paxton Henderson, a singer-songwriter whose rock stylings are influenced by his extensive jazz guitar training. 🎸

Come out from 6–8:30 PM on the first Friday of each month this summer for free performances by exceptional area musicians!

06/02/2026

We’re excited for this Saturday’s Sip Into Summer Wine Festival at Woodbrook Farm Vineyard. Chiswell will be one of the dozen wineries pouring from 12–5 PM on Woodbrook’s beautiful grounds, with live music and food truck fare.

Get tickets and find more details (including our exclusive Crown Club discount!) at the link below:

Chiswell will be one of ten Virginia wineries pouring at Woodbrook Farm Vineyard from 12–5 PM on Saturday, June 6!

06/01/2026

The summer is starting to come together at Chiswell! ☀️

Join us for Summer Sundown, our monthly outdoor performances on first Fridays. Then on the third Thursday of each month, Rachael Karpo hosts live events like her Music Trivia Night on 6/18.

Find the full summer calendar at chiswell.wine/events

05/30/2026

Join us next Friday, June 5, for live music out on the lawn starting at 6 PM!

🎸 .music.art will be playing, combining rock and jazz guitar into an impressive range of styles and influences.

Our free summer concert series takes place on the first Friday of every month through October, so come sip and savor the Blue Ridge evening glow with us!