The Miles Davis estate might want to send Michael Dorf a thank-you card. He’s paid for “Kind of Blue” at least four times.
Dorf first owned Davis’s masterpiece on vinyl. Then he switched to CD. When MP3s became a thing, he spent “tens of thousands of dollars” on iTunes. Now he’s buying “Kind of Blue” and all his other favorite records all over again — on vinyl. “I’m the biggest jerk ever,” he jokes.
The music of Dorf’s life has been an expensive preoccupation; from an early age, he made it his livelihood. At 23, he founded the Knitting Factory, the New York City nightclub that became a hub of “downtown” rock and jazz. About a decade ago, Dorf — now in his 50s — opened the inaugural room in his next venture, City Winery, combining fine food and an extensive wine list with live performance.
Now, after expanding the City Winery concept to Chicago, Nashville, Atlanta, and Washington, D.C., Dorf and his team are preparing to throw open the doors on their latest upscale outpost, in Boston.
“We’re looking for cosmopolitan, sexy cities, ones with sophisticated audiences that have a deep interest in culture and the culinary arts,” Dorf says.
The newest City Winery is scheduled to open Nov. 10, with David Crosby slated to play the 300-capacity showroom on Nov. 13. Other upcoming headliners include Rufus Wainwright, Suzanne Vega, and, on New Year’s Eve, Los Lobos. Construction delays had forced the staff to move some early bookings — Max Weinberg, Cowboy Junkies, Shawn Colvin — to alternate venues.
For Dorf, the idea behind City Winery was simple. It was “absolutely a selfish, hedonistic exercise,” he says.
Nights out with his wife became increasingly rare, raising a family while managing a busy schedule. When they made time, Dorf came to expect a few creature comforts. He wanted a nice glass of wine. He wanted to know his steak was a choice, grass-fed cut of meat. Most of all, if he was catching a show, he wanted to know he had a good seat waiting, even if he was running late.
And he knew there were plenty of people who shared his expectations. What’s more, having worked for years as a promoter, he knew the acts he booked were looking for some amenities of their own.
As the City Winery empire continues to grow, Dorf says, artists such as Art Garfunkel and Rickie Lee Jones (she’s scheduled to appear in Boston in March) can count on 20 or 30 dates in a given year at venues where they know they’ll be pampered and well-compensated.
There’s a simple mantra behind the whole concept, he says: “Indulge your senses.”
The new Boston location sits just around the corner from the TD Garden and Haymarket Square, on the edge of what’s left of the West End. At a whopping 30,000 square feet, it’s an ambitious undertaking. There’s the performance showroom, a vast dining space, and City Winery’s trademark in-house winemaking operation. There are also private rooms for parties, fund-raisers, wine classes, and intimate concerts. Decor-wise, the dominant themes are soft curves, high-end mood lighting, and lots of glass, all blended with rustic themes — red brick, reclaimed wood, ceiling baffles made from barrel staves.
The idea for customers is to “choose your own adventure,” says Greg Kitowicz, City Winery’s vice president of business and venue development. There’s a central “concierge desk” to direct traffic flow. One alcove will feature Dorf’s personal collection of paintings by Henry Schwartz, the late Boston Expressionist.
When Peter Wolf showed up to play the City Winery in Chicago, he was drawn to one of the paintings.
“Is that Henry Schwartz?” he asked, according to Kitowicz. “He taught me to paint 30 years ago.”
Each City Winery features custom nods to the local fare. In Nashville, they’ve got hot chicken. In Atlanta, the star of the menu is shrimp and grits. The Boston location will emphasize a raw bar, says Kitowicz, who grew up in Rhode Island. (The concept of a winery-restaurant might have seemed less novel in northern California’s wine country, where a City Winery venue in the Napa Valley Opera House closed in January 2016 after less than two years in business.)
The head chef is Enx Dadulas, late of Ohana in Gloucester and a onetime mentee of both Roy Yamaguchi and Barbara Lynch. General manager Keven Halopoff comes to City Winery from The Sinclair in Cambridge.
“The executive team is like the Bad News Bears, unique people from all kinds of backgrounds,” Dorf says with a laugh. They share deep experience in the hospitality business, but they’re also “real individuals. Keven is probably the only underwater certified welder in all of Boston.”
With a total occupancy just north of 800, scale is crucial to the concept. Kitowicz believes City Winery breaks more Riedel wine glasses than anyone in the country.
But the occasional sound of shattering glass is one price they’ll gladly pay to put a little wine on your lips and other, more appealing sounds in your ears. Of all the facts and figures about the business, there’s one number they’re especially proud to tout: In the showroom, Kitowicz says, “we shush people more than any other venue.”James Sullivan can be reached at email@example.com. Follow him on Twitter @sullivanjames.