Events


From time to time, we host special small-group experiences. We hope you’ll join us at the next event!

April 2024
Watercolor poppy flower for Chiswell artisan pop-up

Artisan Pop-up: Tess Sherman

Tess is a self-taught artist who enjoys creating beauty and a colorful aesthetic. Visit us on April 20 and 21 to shop her watercolor paintings!
More Details
SATURDAY, APR. 20 & SUNDAY, APR. 21
Chiswell Farm & Winery
430 Greenwood Road, Greenwood, VA 22943
Monticello AVA Wine Week Sparkling Brunch graphic from Monticello Wine Trail

Monticello Wine Week: Sparkling Brunch

Sip on exquisite sparkling wines from Chiswell and other Monticello Wine Trail wineries as part of the Monticello Wine Week celebrations!
More Details
Sunday, Apr. 28
Water’s Edge at Mount Ida Reserve
6155 Rolling Road South, Scottsville, Virginia 24590
May 2024
Welcome Corks & Collage

Corks & Collage Series: Welcome

This event welcomes guests to sip on Chiswell wine and create unique collages to take home.
More Details
Sunday, May. 12
Chiswell Farm & Winery
430 Greenwood Road, Greenwood, VA 22943

Summer Sundown

Join us for live music, Virginia wine, and summer sunsets from mid-May–September.
More Details
Fridays, May 17–September 27
Chiswell Farm & Winery
430 Greenwood Road, Greenwood, VA 22943

Summer Sundown

Join us for live music, Virginia wine, and summer sunsets from mid-May–September.
More Details
Fridays, May 17–September 27
Chiswell Farm & Winery
430 Greenwood Road, Greenwood, VA 22943
Mother, father, and son drinking wine at Chiswell

Sippin’ Sunday

A daytime escape to the Greenwood countryside is exactly what you need to unwind before the week ahead.
More Details
Sundays, May 26–November 10
Chiswell Farm & Winery
430 Greenwood Road, Greenwood, VA 22943
2 Wishes Band

Sippin’ Monday

A daytime escape to the Greenwood countryside is exactly what you need to unwind on Memorial Day.
More Details
Monday, May. 27
Chiswell Farm & Winery
430 Greenwood Road, Greenwood, VA 22943

Summer Sundown

Join us for live music, Virginia wine, and summer sunsets from mid-May–September.
More Details
Fridays, May 17–September 27
Chiswell Farm & Winery
430 Greenwood Road, Greenwood, VA 22943
June 2024
Dapper Dad Market Saturday June 1st 2024

Dapper Dad Market

Wine and finds for Dad! Hosted by the Heart of Virginia Artisans
More Details
Saturday, Jun. 1
Chiswell Farm & Winery
430 Greenwood Road, Greenwood, VA 22943
Mother, father, and son drinking wine at Chiswell

Sippin’ Sunday

A daytime escape to the Greenwood countryside is exactly what you need to unwind before the week ahead.
More Details
Sundays, May 26–November 10
Chiswell Farm & Winery
430 Greenwood Road, Greenwood, VA 22943

Summer Sundown

Join us for live music, Virginia wine, and summer sunsets from mid-May–September.
More Details
Fridays, May 17–September 27
Chiswell Farm & Winery
430 Greenwood Road, Greenwood, VA 22943
Poppies painting by Adam Reinhard

Painting Workshop with Adam

Paint your own “Poppies” on canvas with artistic guidance from Adam Reinhard.
More Details
Sunday, Jun. 9
Chiswell Farm & Winery
430 Greenwood Road, Greenwood, VA 22943
Mother, father, and son drinking wine at Chiswell

Sippin’ Sunday

A daytime escape to the Greenwood countryside is exactly what you need to unwind before the week ahead.
More Details
Sundays, May 26–November 10
Chiswell Farm & Winery
430 Greenwood Road, Greenwood, VA 22943

Summer Sundown

Join us for live music, Virginia wine, and summer sunsets from mid-May–September.
More Details
Fridays, May 17–September 27
Chiswell Farm & Winery
430 Greenwood Road, Greenwood, VA 22943
Mother, father, and son drinking wine at Chiswell

Sippin’ Sunday

A daytime escape to the Greenwood countryside is exactly what you need to unwind before the week ahead.
More Details
Sundays, May 26–November 10
Chiswell Farm & Winery
430 Greenwood Road, Greenwood, VA 22943

Summer Sundown

Join us for live music, Virginia wine, and summer sunsets from mid-May–September.
More Details
Fridays, May 17–September 27
Chiswell Farm & Winery
430 Greenwood Road, Greenwood, VA 22943
Mother, father, and son drinking wine at Chiswell

Sippin’ Sunday

A daytime escape to the Greenwood countryside is exactly what you need to unwind before the week ahead.
More Details
Sundays, May 26–November 10
Chiswell Farm & Winery
430 Greenwood Road, Greenwood, VA 22943

Summer Sundown

Join us for live music, Virginia wine, and summer sunsets from mid-May–September.
More Details
Fridays, May 17–September 27
Chiswell Farm & Winery
430 Greenwood Road, Greenwood, VA 22943
Mother, father, and son drinking wine at Chiswell

Sippin’ Sunday

A daytime escape to the Greenwood countryside is exactly what you need to unwind before the week ahead.
More Details
Sundays, May 26–November 10
Chiswell Farm & Winery
430 Greenwood Road, Greenwood, VA 22943
July 2024

Summer Sundown

Join us for live music, Virginia wine, and summer sunsets from mid-May–September.
More Details
Fridays, May 17–September 27
Chiswell Farm & Winery
430 Greenwood Road, Greenwood, VA 22943
Birch tree painting by Adam Reinhard

Painting Workshop with Adam

Paint your own “Birch Tree” on canvas with artistic guidance from Adam Reinhard.
More Details
Sunday, Jul. 7
Chiswell Farm & Winery
430 Greenwood Road, Greenwood, VA 22943
Mother, father, and son drinking wine at Chiswell

Sippin’ Sunday

A daytime escape to the Greenwood countryside is exactly what you need to unwind before the week ahead.
More Details
Sundays, May 26–November 10
Chiswell Farm & Winery
430 Greenwood Road, Greenwood, VA 22943

Summer Sundown

Join us for live music, Virginia wine, and summer sunsets from mid-May–September.
More Details
Fridays, May 17–September 27
Chiswell Farm & Winery
430 Greenwood Road, Greenwood, VA 22943
Mother, father, and son drinking wine at Chiswell

Sippin’ Sunday

A daytime escape to the Greenwood countryside is exactly what you need to unwind before the week ahead.
More Details
Sundays, May 26–November 10
Chiswell Farm & Winery
430 Greenwood Road, Greenwood, VA 22943

Summer Sundown

Join us for live music, Virginia wine, and summer sunsets from mid-May–September.
More Details
Fridays, May 17–September 27
Chiswell Farm & Winery
430 Greenwood Road, Greenwood, VA 22943
Mother, father, and son drinking wine at Chiswell

Sippin’ Sunday

A daytime escape to the Greenwood countryside is exactly what you need to unwind before the week ahead.
More Details
Sundays, May 26–November 10
Chiswell Farm & Winery
430 Greenwood Road, Greenwood, VA 22943

Summer Sundown

Join us for live music, Virginia wine, and summer sunsets from mid-May–September.
More Details
Fridays, May 17–September 27
Chiswell Farm & Winery
430 Greenwood Road, Greenwood, VA 22943
Mother, father, and son drinking wine at Chiswell

Sippin’ Sunday

A daytime escape to the Greenwood countryside is exactly what you need to unwind before the week ahead.
More Details
Sundays, May 26–November 10
Chiswell Farm & Winery
430 Greenwood Road, Greenwood, VA 22943
No Upcoming Events

Check back soon!

Load More

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!

Ceremony space at Chiswell Winery wedding venue in Charlottesville

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.