WEEKENDR

← Back to Venues

Winery

Glass House

Glass House Winery is a boutique winery and brewery in central Virginia, founded in 2006 and part of the Monticello Wine Trail near Charlottesville. Known for its tropical flair, the estate grows and cultivates its own grapes to make artisan wines that reflect the terroir of the region, and it has since added the Glass House Brewery to its offerings. Beyond wine and beer, the venue is known for its handcrafted chocolates and its distinctive glass conservatory setting. Weekends often feature live music with local artists, along with special events such as chef-led brunches. Visitors can also extend their stay at the on-site bed and breakfast, making Glass House a destination for a full weekend getaway in Virginia wine country.

Glass House is a winery in Free Union, Virginia, part of the Crozet & Western Albemarle area of Charlottesville wine country. Amenities include dogs, outdoor seating, outside food, weddings. There are 4 upcoming events on the calendar — see the full list below, or browse more events in the area on the events calendar. Explore more of Crozet & Western Albemarle.

Upcoming events at Glass House

Chickenhead Blues Band with Canelos Burritos at Glass House
Music

Chickenhead Blues Band with Canelos Burritos

Glass House
Fri, Oct 23, 2026
6:00 PM – 8:30 PM

Kick off the weekend with the "New Orleans boogie-woogie, upbeat, rhythm and blues" sounds of the Chickenhead Blues Band, performing live inside the glass house conservatory. Friday, October 23rd, 6 to 8:30pm. No cover. Open to all. Band: Aric van Brocklin – Guitar, Skip Haga – Keyboards, Jeff Louderback – Drums, Jack Sheehan – Sax, Vic Brown – Bass. Canelos Burritos food truck will be onsite with service beginning at 5:30pm. Seating indoors and outdoors is first come, no reservations. Picnics welcome (no outside alcohol). Children and leashed, well-behaved dogs welcome.

More Info
Greg Ward at Glass House
Music

Greg Ward

Glass House
Sun, Oct 25, 2026
2:00 PM – 5:00 PM

A stellar Sunday FunDay with Greg Ward returning to the tropical oasis, sharing positive vibes and groovy reggae sounds live. Sunday, October 25th, 2 to 5pm. Open to all. No cover. More about Greg Ward: https://gregwardmusic.com/ Seating indoors and outdoors is first come, no reservations. Picnics welcome (no outside alcohol). Children and leashed, well-behaved dogs welcome.

More Info
Dara James and the Soul Disciples at Glass House
Music

Dara James and the Soul Disciples

Glass House
Fri, Oct 30, 2026
6:00 PM – 8:30 PM

Dara James and the Soul Disciples return to Free Union with Blues, R&B, and a whole lot of SOUL! Featuring Dara James on guitar and vocals, Eric Franzen on organ, and Jeff Louderback on drums. Friday, October 30th, 6 to 8:30pm. Open to all. No cover. Canelos Burritos food truck will be onsite with service beginning at 5:30pm. Seating indoors and outdoors is first come, no reservations. Picnics welcome (no outside alcohol). Children and leashed, well-behaved dogs welcome.

More Info
Halloween Party with music by Doctor Rhythm featuring King Gypsy and Jones Catering at Glass House
Music

Halloween Party with music by Doctor Rhythm featuring King Gypsy and Jones Catering

Glass House
Sat, Oct 31, 2026
5:00 PM – 8:00 PM

Halloween fun – put on your costumes (if you so choose) and groove to the funky beats of Doctor Rhythm featuring King Gypsy. R&B, Blues, Soul, and Reggae tunes in the spooky tropical oasis. Saturday, October 31st, 5 to 8pm. No cover. Open to all. Jones Catering will be onsite with burgers, dogs, wings, fries and more, service beginning by 5:00pm. Seating indoors and outdoors is first come, no reservations. Picnics welcome (no outside alcohol). Children and leashed, well-behaved dogs welcome.

More Info

Past events

What to expect

Nearby wineries & breweries

All venues and events in Crozet & Western Albemarle ❧

Planning a trip? Things to do this weekend · Today · All events