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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 6 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

Ian Gilliam & The FireKings with Canelos Burritos food truck at Glass House
Music

Ian Gilliam & The FireKings with Canelos Burritos food truck

Fri, Nov 13, 2026
6:00 PM – 8:30 PM

We’re kicking off the weekend with Ian Gilliam & The FireKings. They’ll be treating us all to their incredible “Blues, Rockabilly, Honky Tonk, and Rock & Roll music” live inside the cozy confines of our tropical oasis. Friday, November 13th, from 6 to 8:30pm. No cover. Open to all.

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Perennial Collection at Glass House
Music

Perennial Collection

Sat, Nov 14, 2026
5:00 PM – 8:00 PM

We are delighted to have Perennial Collection returning to our tropical oasis! “Featuring female led vocal covers of R&B, Soul, Hip-Hop, and Jazz! Perennial Collection delivers dynamic vocal harmonies and jazz-infused arrangements to please the ear and move your feet.” Saturday, November 14th, from 5 to 8pm. Open to all. No cover.

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Wavelength with Special Guest Bob Bennetta at Glass House
Music

Wavelength with Special Guest Bob Bennetta

Sun, Nov 15, 2026
2:00 PM – 5:00 PM

Legendary jazz pianist Bob Bennetta joins the trio for an afternoon of blues and jazz, and will also be doing lead vocals! Sam Green – bass, Larry Bisgaier – guitar/vocals, Waverly Milor – harmonica/vocals. Sunday, November 15, from 2 to 5pm. Open to all. No cover.

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Past events


What to expect


Nearby wineries & breweries

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