music · Tasting Room
Calysta Cheyenne Live in the Barrel Room
Calysta Cheyenne sings jazz standards from the Great American Songbook, trained at Berklee. Live in the Barrel Room, no reservation needed.
More from Calysta → · Photo: Bob Williams
- When
- Saturday, October 17, 2026 · 6 PM – 8 PM
- Where
- Tasting Room · 322 N Pioneer St, Ashland, OR 97520
What to expect
Saturday Night: Music or Comedy
Live music or comedy every Saturday night, with wine that takes itself far less seriously than it should.
About 2 hours · Parties up to 8
Plan your visit
Getting here
We're at 322 N Pioneer St, Ashland, OR 97520, in the tasting room and Barrel Room downtown. Regular hours: Thu – Sat 2 – 7 PM · Sun 2 – 6 PM. Questions? Call +1 541 708 1272.
Good to know
Before you come.
Do I need a ticket or a reservation?
A reservation isn't required, but it's the only way to be sure of a table. Use Reserve a tasting above to hold one for Sat, Oct 17.
What does it cost?
There's no cover charge. Wine is by the glass, the flight, or the bottle.
Can I bring my kids?
Sure, as long as they don't use the barrels as bongos. We're family-friendly.
Are dogs allowed?
Yes, if they're cool. If your dog's nicer than most humans — perfect. If not, maybe let them guard the couch instead.
What kind of wine do you make?
Syrah, Malbec, Cab Sauv, Tempranillo, Sauvy B, Chenin Blanc, Rosé, and whatever other rebellious surprises we bottled last.
Can I host my event here?
Heck ya! We love throwing parties. Birthdays, shows, divorces, board meetings — we don't judge. Just know the wine will upstage your PowerPoint.
What should I wear?
Whatever you can spill Syrah on without crying. Although, Lin usually has a Tide Stick in their bag for emergencies. Somm things.
Will there be food?
Yes! We have a fresh food program supplied by The Allium Wood-Fired Pizza, parked right out back. Charcuterie, empanadas, wood-fired pies, pastas, salads, potato-chip pairings, and artisan chocolates. Plan on coming hungry.
Also coming up