Upcoming Events
From time to time, we host special small-group experiences. We hope you’ll join us at the next event!
June 2026
Sip Into Summer Wine Festival at Woodbrook Farm Vineyard
Chiswell will be one of ten Virginia wineries pouring at Woodbrook Farm Vineyard from 12–5 PM on Saturday, June 6!
More Details
Crown Club Saturday: Summer Picnic
Members and their guests are invited to our annual summer picnic on 6/13, featuring Brownsville Market’s fried chicken! Sign up by June 8.
More Details
Music Trivia Night with Rachael Karpo
On the third Thursday of each month, Rachael Karpo is hosting either music trivia or karaoke night at Chiswell — and it’s free to attend!
More Details
July 2026
Summer Sundown
Local musicians and food trucks help us savor the Friday evening sunset once a month from May through October, 6–8:30 PM.
More Details
🌻Virginia Sunflower Fest
Wander through vibrant sunflower fields, enjoy live music and food trucks, capture unforgettable moments with family, and sip local wine. From sunflower picking to an educational walking trail, it’s the ultimate summer escape. Tickets required.
More Details
🌻Virginia Sunflower Fest
Wander through vibrant sunflower fields, enjoy live music and food trucks, capture unforgettable moments with family, and sip local wine. From sunflower picking to an educational walking trail, it’s the ultimate summer escape. Tickets required.
More Details
🌻Virginia Sunflower Fest
Wander through vibrant sunflower fields, enjoy live music and food trucks, capture unforgettable moments with family, and sip local wine. From sunflower picking to an educational walking trail, it’s the ultimate summer escape. Tickets required.
More Details
🌻Virginia Sunflower Fest
Wander through vibrant sunflower fields, enjoy live music and food trucks, capture unforgettable moments with family, and sip local wine. From sunflower picking to an educational walking trail, it’s the ultimate summer escape. Tickets required.
More Details
🌻Virginia Sunflower Fest
Wander through vibrant sunflower fields, enjoy live music and food trucks, capture unforgettable moments with family, and sip local wine. From sunflower picking to an educational walking trail, it’s the ultimate summer escape. Tickets required.
More Details
Karaoke Night with Rachael Karpo
On the third Thursday of each month, Rachael Karpo is hosting either music trivia or karaoke night at Chiswell — and it’s free to attend!
More Details
🌻Virginia Sunflower Fest
Wander through vibrant sunflower fields, enjoy live music and food trucks, capture unforgettable moments with family, and sip local wine. From sunflower picking to an educational walking trail, it’s the ultimate summer escape. Tickets required.
More Details
🌻Virginia Sunflower Fest
Wander through vibrant sunflower fields, enjoy live music and food trucks, capture unforgettable moments with family, and sip local wine. From sunflower picking to an educational walking trail, it’s the ultimate summer escape. Tickets required.
More Details
🌻Virginia Sunflower Fest
Wander through vibrant sunflower fields, enjoy live music and food trucks, capture unforgettable moments with family, and sip local wine. From sunflower picking to an educational walking trail, it’s the ultimate summer escape. Tickets required.
More Details
🌻Virginia Sunflower Fest
Wander through vibrant sunflower fields, enjoy live music and food trucks, capture unforgettable moments with family, and sip local wine. From sunflower picking to an educational walking trail, it’s the ultimate summer escape. Tickets required.
More Details
🌻Virginia Sunflower Fest
Wander through vibrant sunflower fields, enjoy live music and food trucks, capture unforgettable moments with family, and sip local wine. From sunflower picking to an educational walking trail, it’s the ultimate summer escape. Tickets required.
More Details
🌻Virginia Sunflower Fest
Wander through vibrant sunflower fields, enjoy live music and food trucks, capture unforgettable moments with family, and sip local wine. From sunflower picking to an educational walking trail, it’s the ultimate summer escape. Tickets required.
More Details
🌻Virginia Sunflower Fest
Wander through vibrant sunflower fields, enjoy live music and food trucks, capture unforgettable moments with family, and sip local wine. From sunflower picking to an educational walking trail, it’s the ultimate summer escape. Tickets required.
More Details
Chiswell Book Club July Meeting
Every other month, the Chiswell Book Club meets to discuss a new book. Join us for a Sunday afternoon of wine and discussion!
More Details
🌻Virginia Sunflower Fest
Wander through vibrant sunflower fields, enjoy live music and food trucks, capture unforgettable moments with family, and sip local wine. From sunflower picking to an educational walking trail, it’s the ultimate summer escape. Tickets required.
More Details
🌻Virginia Sunflower Fest
Wander through vibrant sunflower fields, enjoy live music and food trucks, capture unforgettable moments with family, and sip local wine. From sunflower picking to an educational walking trail, it’s the ultimate summer escape. Tickets required.
More Details
August 2026
🌻Virginia Sunflower Fest
Wander through vibrant sunflower fields, enjoy live music and food trucks, capture unforgettable moments with family, and sip local wine. From sunflower picking to an educational walking trail, it’s the ultimate summer escape. Tickets required.
More Details
🌻Virginia Sunflower Fest
Wander through vibrant sunflower fields, enjoy live music and food trucks, capture unforgettable moments with family, and sip local wine. From sunflower picking to an educational walking trail, it’s the ultimate summer escape. Tickets required.
More Details
Summer Sundown
Local musicians and food trucks help us savor the Friday evening sunset once a month from May through October, 6–8:30 PM.
More Details
Music Trivia Night with Rachael Karpo
On the third Thursday of each month, Rachael Karpo is hosting either music trivia or karaoke night at Chiswell — and it’s free to attend!
More Details
September 2026
Summer Sundown
Local musicians and food trucks help us savor the Friday evening sunset once a month from May through October, 6–8:30 PM.
More Details
Sippin’ Monday: Labor Day
Spend your holiday enjoying wine and live music at Chiswell! Local acoustic musicians will perform from 1–4 PM on Monday, September 7, 2026.
More Details
Karaoke Night with Rachael Karpo
On the third Thursday of each month, Rachael Karpo is hosting either music trivia or karaoke night at Chiswell — and it’s free to attend!
More Details
Chiswell Book Club September Meeting
Every other month, the Chiswell Book Club meets to discuss a new book. Join us for a Sunday afternoon of wine and discussion!
More Details
October 2026
Summer Sundown
Local musicians and food trucks help us savor the Friday evening sunset once a month from May through October, 6–8:30 PM.
More Details
Music Trivia Night with Rachael Karpo
On the third Thursday of each month, Rachael Karpo is hosting either music trivia or karaoke night at Chiswell — and it’s free to attend!
More Details
No Upcoming Events
Check back soon!
Get the Latest
Join our mailing list to get news about upcoming events, including wine releases and on-site local vendors, delivered right to your inbox. With limited space at each event, it’s best to reserve your spot ahead of time!
Wedding Events
Beyond our seasonal calendar of unique winery events, Chiswell boasts a gorgeous outdoor space to host wedding ceremonies and celebrations. With stunning outdoor views and a selection of award-winning wine, we hope that the property will serve as a grounding place to begin this next chapter in your life.
