Kick off your weekend with the awesome sounds of The Oversteppers Reggae Trio! The Oversteppers, one of Virginia’s premier reggae bands, was founded by Chris Leva in 2019. Fellow members Gabe Gavin and Stephen Barling join Chris to form a trio with acoustic guitars and electric bass for smaller venues, performing classic reggae covers and original songs as well. All the fun happens live inside our tropical space on Friday, October 4th, from 6-8:30 pm. No cover. Open to all.

Keep up with The Oversteppers via their Facebook page: https://www.facebook.com/theoversteppers

Sweet Jane’s Kitchen will be onsite offering their incredibly delicious Maryland style Crab Cake Sandwiches. https://www.ilovesweetjaneskitchen.com/

Our live music events typically take place within the beautiful space of the glass conservatory, our indoor tropical oasis. On occasion, the music may perform outdoors, under the eaves of the back deck. Both indoor and outdoor seating is available first come, no reservations.

Picnics are welcome throughout the property, barring any outside alcohol. We have plentiful seating areas both inside the conservatory, and outdoors along the back deck, as well as in front of the conservatory, and there are several picnic tables spread across the lakefront. Feel free to bring your blankets/chairs. Pop up tents and personal grills are permitted for use in the overflow grassy tailgate and picnic areas.

Glass House Winery wines are available by the bottle and glass, and traditional tastings are being conducted at the Tasting Room Bar. Wine Flights are also available, these are great for those who prefer to do a self guided tasting, simply order at the bar and take back to your table.

Children are welcome, please supervise them at all times. Consider bringing along games or other items to entertain them while seated.

Well behaved dogs are also welcome but must remain on their leash at all times.

Turn up the heat on your Saturday plans with the spicy rhythms, zesty beats, and sizzling sounds of our favorite Latin and Gypsy Rumba Guitar Duo – Berto Sales and Vincent Zorn. Returning to our tropical oasis for an afternoon show. Saturday, October 5th, from 2:30 to 5:30pm. Open to all. No cover.

More on the musicians:

Berto of Beleza Music – https://www.facebook.com/BelezaMusic/

Vincent Zorn – Charlottesville Virginia Rumba Flamenco Guitarist –
https://www.facebook.com/vincent.zorn/

Our live music events typically take place within the beautiful space of the glass conservatory, our indoor tropical oasis. On occasion, the music may perform outdoors, under the eaves of the back deck. Both indoor and outdoor seating is available first come, no reservations.

Picnics are welcome throughout the property, barring any outside alcohol. We have plentiful seating areas both inside the conservatory, and outdoors along the back deck, as well as in front of the conservatory, and there are several picnic tables spread across the lakefront. Feel free to bring your blankets/chairs. Pop up tents and personal grills are permitted for use in the overflow grassy tailgate and picnic areas.

Glass House Winery wines are available by the bottle and glass, and traditional tastings are being conducted at the Tasting Room Bar.

Wine Flights are also available, these are great for those who prefer to do a self guided tasting, simply order at the bar and take back to your table.

Children are welcome, please supervise them at all times. Consider bringing along games or other items to entertain them while seated.

Well behaved dogs are also welcome but must remain on their leash at all times.

It’s going to be a terrific Sunday Fun Day with local singer/songwriter Matt Johnson returning to our slice of paradise here in the tropics of Free Union. Sunday, October 6th, from 2 to 5pm. Open to all. No cover.

Follow Matt Johnson’s musical journey via his Facebook page:
https://www.facebook.com/MattJSings

Our live music events typically take place within the beautiful space of the glass conservatory, our indoor tropical oasis. On occasion, the music may perform outdoors, under the eaves of the back deck. Both indoor and outdoor seating is available first come, no reservations.

Picnics are welcome throughout the property, barring any outside alcohol. We have plentiful seating areas both inside the conservatory, and outdoors along the back deck, as well as in front of the conservatory, and there are several picnic tables spread across the lakefront. Feel free to bring your blankets/chairs. Pop up tents and personal grills are permitted for use in the overflow grassy tailgate and picnic areas.

Glass House Winery wines are available by the bottle and glass, and traditional tastings are being conducted at the Tasting Room Bar. Wine Flights are also available, these are great for those who prefer to do a self guided tasting, simply order at the bar and take back to your table.

Children are welcome, please supervise them at all times. Consider bringing along games or other items to entertain them while seated.

Well behaved dogs are also welcome but must remain on their leash at all times.

It’s going to be a super Saturday evening here in the tropics of Free Union with The Dagga Boys raising the roof of the glass house with their awesome sounds! October 12th from 5 to 8pm. Open to all. No cover.

The Dagga Boys bring together two of Central Viriginia’s most popular singer/songwriters and guitar pickers – Ken Farmer (of Antiques Road Show fame) and Jon Spear. Their sound neatly blends Ken’s background as an extraordinary blues & bluegrass picker and Jon’s penchant for old school rock and folk music, a combination that will delight and entertain you.

For this one-time special show at Glass House, John Stubblefield will be playing drums as an honorary Dagga Boy.

The term Dagga Boy describes the old and sometimes solitary Cape Buffalo which, despite its age, should never to be underestimated and can take down a full-grown lion.

Keep up with the musicians via their respective Facebook pages:

Jon Spear Music page – https://www.facebook.com/jonspearmusic

Ken Farmer & the Authenticators – https://www.facebook.com/kenfarmerandtheauthenticators

Our live music events typically take place within the beautiful space of the glass conservatory, our indoor tropical oasis. On occasion, the music may perform outdoors, under the eaves of the back deck. Both indoor and outdoor seating is available first come, no reservations.

Picnics are welcome throughout the property, barring any outside alcohol. We have plentiful seating areas both inside the conservatory, and outdoors along the back deck, as well as in front of the conservatory, and there are several picnic tables spread across the lakefront. Feel free to bring your blankets/chairs. Pop up tents and personal grills are permitted for use in the overflow grassy tailgate and picnic areas.

Glass House Winery wines are available by the bottle and glass, and traditional tastings are being conducted at the Tasting Room Bar. Wine Flights are also available, these are great for those who prefer to do a self guided tasting, simply order at the bar and take back to your table.

Children are welcome, please supervise them at all times. Consider bringing along games or other items to entertain them while seated.

Well behaved dogs are also welcome but must remain on their leash at all times. 

It’s going to be an incredible afternoon of great music and lots of fun with Scuffletown returning to our slice of paradise here in Free Union. The Scuffletown duo of Marc and John will fill our tropical conservatory with their awesome calypso, bluegrass, reggae, and blues. Sunday, October 13th, from 2 to 5pm. Open to all. No cover.

Learn more about Scuffletown at their website – http://www.scuffletownmusic.com/

…and keep up with their everyday happenings on Facebook – https://www.facebook.com/Scuffletown-192314870822883/

Our live music events typically take place within the beautiful space of the glass conservatory, our indoor tropical oasis. On occasion, the music may perform outdoors, under the eaves of the back deck. Both indoor and outdoor seating is available first come, no reservations.

Picnics are welcome throughout the property, barring any outside alcohol. We have plentiful seating areas both inside the conservatory, and outdoors along the back deck, as well as in front of the conservatory, and there are several picnic tables spread across the lakefront. Feel free to bring your blankets/chairs. Pop up tents and personal grills are permitted for use in the overflow grassy tailgate and picnic areas.

Glass House Winery wines are available by the bottle and glass, and traditional tastings are being conducted at the Tasting Room Bar. Wine Flights are also available, these are great for those who prefer to do a self guided tasting, simply order at the bar and take back to your table.

Children are welcome, please supervise them at all times. Consider bringing along games or other items to entertain them while seated.

Well behaved dogs are also welcome but must remain on their leash at all times.

We are super stoked to have G.G.R.H. return to our slice of paradise here in Free Union. Featuring 4 Charlottesville musical institutions — guitar slinger Ian Gilliam, harmonica player Gary Green, bassist Steve Riggs, and Eddie Hall on drums. The musicality of this foursome is insane, making for an incredible performance that you won’t want to miss! Friday, October 18th, from 6 to 8:30pm. Open to all. no cover.

Keep up with GGRH and their musical happenings via their Facebook page –
https://www.facebook.com/GGRH-102894869052076/

Two Brothers Southwestern Grill food truck will be onsite, beginning at 5:30pm. Offering a menu of their incredibly fresh and flavorful dishes. https://www.facebook.com/profile.php?id=100054605403300

Our live music events typically take place within the beautiful space of the glass conservatory, our indoor tropical oasis. On occasion, the music may perform outdoors, under the eaves of the back deck. Both indoor and outdoor seating is available first come, no reservations.

Picnics are welcome throughout the property, barring any outside alcohol. We have plentiful seating areas both inside the conservatory, and outdoors along the back deck, as well as in front of the conservatory, and there are several picnic tables spread across the lakefront. Feel free to bring your blankets/chairs. Pop up tents and personal grills are permitted for use in the overflow grassy tailgate and picnic areas.

Glass House Winery wines are available by the bottle and glass, and traditional tastings are being conducted at the Tasting Room Bar. Wine Flights are also available, these are great for those who prefer to do a self guided tasting, simply order at the bar and take back to your table.

Children are welcome, please supervise them at all times. Consider bringing along games or other items to entertain them while seated.

Well behaved dogs are also welcome but must remain on their leash at all times.

The Michael Elswick Gathering returns to our tropical oasis here in Free Union. Entertaining all with their Jazz, Blues, Ballads & Latin tunes. Saturday evening, October 19th from 5 to 8pm. Open to all. No cover.

Featuring:
Michael Elswick – Saxes
Bill Edmonds – Guitar and Vocals
Liz Barnes – Keyboards
Tom Harbeck – Bass
David Drubin – Drums

(*Occasionally there are changes to band members and updates are made based on info received ahead of the scheduled date.)

Our live music events typically take place within the beautiful space of the glass conservatory, our indoor tropical oasis. On occasion, the music may perform outdoors, under the eaves of the back deck. Both indoor and outdoor seating is available first come, no reservations.

Picnics are welcome throughout the property, barring any outside alcohol. We have plentiful seating areas both inside the conservatory, and outdoors along the back deck, as well as in front of the conservatory, and there are several picnic tables spread across the lakefront. Feel free to bring your blankets/chairs. Pop up tents and personal grills are permitted for use in the overflow grassy tailgate and picnic areas.

Glass House Winery wines are available by the bottle and glass, and traditional tastings are being conducted at the Tasting Room Bar. Wine Flights are also available, these are great for those who prefer to do a self guided tasting, simply order at the bar and take back to your table.

Children are welcome, please supervise them at all times. Consider bringing along games or other items to entertain them while seated.

Well behaved dogs are also welcome but must remain on their leash at all times. 

We are thrilled to welcome the return of the Central Virginia Blues Society to our slice of paradise here in Free Union. The CVBS is made up of a membership of many of Central Virginia’s finest Blues musicians. The afternoon gathering will be a CVBS Octoberfest JAM, featuring continuous acoustic performances by a variety of Blues musicians inside our tropical conservatory. Sunday, October 20th, from 2 to 5pm. (*Signups of members wishing to perform begin at 1pm.)

Our live music events typically take place within the beautiful space of the glass conservatory, our indoor tropical oasis. On occasion, the music may perform outdoors, under the eaves of the back deck. Both indoor and outdoor seating is available first come, no reservations.

Picnics are welcome throughout the property, barring any outside alcohol. We have plentiful seating areas both inside the conservatory, and outdoors along the back deck, as well as in front of the conservatory, and there are several picnic tables spread across the lakefront. Feel free to bring your blankets/chairs. Pop up tents and personal grills are permitted for use in the overflow grassy tailgate and picnic areas.

Glass House Winery wines are available by the bottle and glass, and traditional tastings are being conducted at the Tasting Room Bar. Wine Flights are also available, these are great for those who prefer to do a self guided tasting, simply order at the bar and take back to your table.

Children are welcome, please supervise them at all times. Consider bringing along games or other items to entertain them while seated.

Well behaved dogs are also welcome but must remain on their leash at all times. 

Jump start your weekend with the sensational “New Orleans boogie-woogie, upbeat, rhythm and blues” sounds of our 4th Friday resident band – the CHICKENHEAD BLUES BAND. Performing live inside our tropical oasis, the glass house conservatory! Friday, October 25th, from 6 to 8:30pm. No cover. Open to all.

Bio:
Chickenhead Blues Band’s history begins in 1999 with weekly legendary Thursday evening shows playing blues tunes at Durty nelly’s pub. A few personnel changes led to the more fusion influenced repertoire presented now. You will hear a taste of New Orleans, Jazz Crusaders, Tom Scott and LA Express, Jimi Hendrix mixed, in with some original songs, as well.

Band members:

Aric van Brocklin – Guitar
Skip Haga – Keyboards
Jeff Louderback – Drums
Andy Rowland – Sax
Vic Brown – Bass

A food truck may be added. Check our social channels for updates. As always, we welcome you to bring outside foods. Pack a picnic, pick-up takeout on your way in, or put together a quick DIY Charcuterie plate with the assorted gourmet food items we carry in the Tasting Room.

Our live music events typically take place within the beautiful space of the glass conservatory, our indoor tropical oasis. On occasion, the music may perform outdoors, under the eaves of the back deck. Both indoor and outdoor seating is available first come, no reservations.

Picnics are welcome throughout the property, barring any outside alcohol. We have plentiful seating areas both inside the conservatory, and outdoors along the back deck, as well as in front of the conservatory, and there are several picnic tables spread across the lakefront. Feel free to bring your blankets/chairs. Pop up tents and personal grills are permitted for use in the overflow grassy tailgate and picnic areas.

Glass House Winery wines are available by the bottle and glass, and traditional tastings are being conducted at the Tasting Room Bar. Wine Flights are also available, these are great for those who prefer to do a self guided tasting, simply order at the bar and take back to your table.

Children are welcome, please supervise them at all times. Consider bringing along games or other items to entertain them while seated.

Well behaved dogs are also welcome but must remain on their leash at all times.

Join us for our annual costume party with the Beleza Trio. Founding members Madeline and Humberto (Berto) Sales will be joined by Matt Wyatt on drums, to lead the fun filled night with their fabulously intoxicating and infectious ‘funkalicious samba soul music’. Saturday, October 26th, from 5 to 8pm. No cover. Open to all. We will remain open until 9pm.

Come dressed up and surprise us with your creativity! (*Costumes are not required, but they do add to the fun.)

More about Beleza and their awesome musical talents —
www.BelezaMusic.com

Keep up with them via Facebook —
Beleza Music – https://www.facebook.com/BelezaMusic/

More about Matt Wyatt and his musical talents:
http://www.mattwyattmusic.com/

A food truck may be added. Check our social channels for updates. As always, we welcome you to bring outside foods. Pack a picnic, pick-up takeout on your way in, or put together a quick DIY Charcuterie plate with the assorted gourmet food items we carry in the Tasting Room.

Our live music events typically take place within the beautiful space of the glass conservatory, our indoor tropical oasis. On occasion, the music may perform outdoors, under the eaves of the back deck. Both indoor and outdoor seating is available first come, no reservations.

Picnics are welcome throughout the property, barring any outside alcohol. We have plentiful seating areas both inside the conservatory, and outdoors along the back deck, as well as in front of the conservatory, and there are several picnic tables spread across the lakefront. Feel free to bring your blankets/chairs. Pop up tents and personal grills are permitted for use in the overflow grassy tailgate and picnic areas.

Glass House Winery wines are available by the bottle and glass, and traditional tastings are being conducted at the Tasting Room Bar. Wine Flights are also available, these are great for those who prefer to do a self guided tasting, simply order at the bar and take back to your table.

Children are welcome, please supervise them at all times. Consider bringing along games or other items to entertain them while seated.

Well behaved dogs are also welcome but must remain on their leash at all times. 

We’re in for an extra special Sunday Fun Day with Louis Smith, of Kendall Street Company, returning to our tropical space. He’ll be treating us to an afternoon filled with his super cool sounds. Sunday, October 27th, from 2 to 5pm. No cover. Open to all.

Louis Smith is a singer-songwriter based out of Charlottesville, VA. He is a versatile acoustical rock’n’roll chameleon playing originals and covers from the likes of Jimi Hendrix to The Avett Brothers. Most nights you can find him rocking front man in Kendall Street Company. But other nights he does his own little thing with his own little spin. This particular set will be all about the laid back Sunday afternoon vibes. Come check out what it’s all about!

Learn more about Louis and his music via the Kendall Street Company website — http://www.kendallstreetcompany.com

Our live music events typically take place within the beautiful space of the glass conservatory, our indoor tropical oasis. On occasion, the music may perform outdoors, under the eaves of the back deck. Both indoor and outdoor seating is available first come, no reservations.

Picnics are welcome throughout the property, barring any outside alcohol. We have plentiful seating areas both inside the conservatory, and outdoors along the back deck, as well as in front of the conservatory, and there are several picnic tables spread across the lakefront. Feel free to bring your blankets/chairs. Pop up tents and personal grills are permitted for use in the overflow grassy tailgate and picnic areas.

Glass House Winery wines are available by the bottle and glass, and traditional tastings are being conducted at the Tasting Room Bar. Wine Flights are also available, these are great for those who prefer to do a self guided tasting, simply order at the bar and take back to your table.

Children are welcome, please supervise them at all times. Consider bringing along games or other items to entertain them while seated.

Well behaved dogs are also welcome but must remain on their leash at all times.