When Michael Dorf founded New York’s Knitting Factory 30 years ago, beer was the beverage of choice for crowds taking in sounds from jazz innovators like John Zorn and rock acts like Sonic Youth. But he always liked wine. “I’m a big fan of Willamette pinot noirs from Oregon,” says Dorf, who now savors his favorites during shows at his latest venture, City Winery, which pours 20 of its own made-on-premises vinos and 400 other bottles from around the world into specialized glassware from centuries-old Austrian maker Riedel. No plastic cups here.

BARRELS OF FUN: City Winery aims to host 300 shows a year at its Boston location.

But music is still the main event. The winery, restaurant and concert venue’s fifth location, City Winery Boston, will host 300 shows a year after it opens on Oct. 16 with a performance by Max Weinberg’s Jukebox, which has the longtime E Street Band drummer fielding requests from a menu of 200 songs. Such headliners will perform in a room with table seating for 300, but Dorf is also excited about the opportunities afforded by a second stage in a smaller space dubbed the Haymarket Lounge. “We can probably squeeze about 100 standing in there for a show, so it’s actually a good little room. It’s about the same size as the original Knitting Factory in New York back in 1987. It allows us to be very artistically free. We’re talking to everyone from some jazz promoters in town to the Berklee School of Music,” Dorf says. “To have a room where we can have a poetry reading or a wine tasting to benefit hurricane victims, it gives us a lot more flexibility. We don’t have that in New York, so it’s a luxury to have a second room to play around with.”

The 30,000-square-foot complex at 1 Canal St. also includes a Mediterranean restaurant with views of the stainless-steel fermentation tanks and French oak barrels in the adjoining glass-walled winery. Lees from the winemaking process wind up in the flatbread pizzas, and much of the wine ends up in kegs with an argon tap system that allows for easy by-the-glass imbibing. To prime our palates, we had national wine director Rachel Speckan pour glasses to pair with three of Dorf’s top shows from the fall concert lineup. ◆

Art Garfunkel • Oct. 26-27

Art Garfunkel. Photo Credit: Gil Cohen Magen

“Art Garfunkel brings resonance and longevity to the stage,” Speckan says of the folk-rock icon, who’s performing two shows fresh off the release of his memoir What Is It All but Luminous. She toasted him with the 2016 City Winery Reserve Chardonnay, a sip she calls “graceful, poised and balanced with a flavorful touch of French oak that harmonizes with the toasty lees, silky texture and ripe orchard fruits.”

Cowboy Junkies • Nov. 2

Cowboy Junkies

“Funky, dirty and earthy music requires a wine of the same kind,” Speckan says, uncorking the 2014 Flowers Vineyard Pinot Noir from California’s Sea View Ridge Estate Vineyard to complement the alt-country stalwarts’ sound. “The Cowboy Junkies inspire this pairing with brambly wild blueberry, tea leaf and wildflowers with gritty spice and rich undertones of structure and serious oak aging.”

Shawn Colvin • Nov. 3-4

Shawn Colvin. Photo Credit: Michael Wilson

“Fresh and breezy lyrics turn gravelly and deep as Shawn Colvin renders an emotional musical moment,” says Speckan, who opted to pair the singer/songwriter with the 2014 Domaine Vincent Paris “Granit 30” from France’s Northern Rhone Valley. “This wine springs from the deep granite and the low point of the hill in Cornas, blended with the tip-top of the hill, creating a wine of depth and weight with lifted aromatics and surprising grip. Violets, plum, pepper and a dash of rusticity pair perfectly with this lovely lady.”

CityWinery 1 Canal St., Boston (617-933-8047) citywinery.com/boston