Pittsfield Mainstay Dottie’s Spreads Community Into New Restaurant, Dorothy’s

If you’ve met someone for coffee in Pittsfield, you’ve been to Dottie’s; that’s just the way it is.

Formally named Dottie’s Coffee Lounge, the coffee shop and community meeting place on North Street, named for owner Jessica Rufo’s grandmother Dorothy, has been open since 2007, and is now a longstanding anchor on Pittsfield’s main drag. In addition to serving baked goods, coffees fancy and simple, breakfast fare and light lunch, the coffee shop is a known community meeting place, and it’s not uncommon to see the side dining room packed with Pittsfield’s business leaders taking a break, working from a laptop, or scheming up some next cool thing.

The shop’s walls are filled with local art (for sale). Colloquially called “Pittsfield’s living room," it’s the space folks use for everything from WordXWord story slams to family fun nights to special themed menu events. Rufo says around 70% of the customers at Dottie’s are regulars. “We’re looking out, we’re taking care of one another. It's definitely a two-way street,” she says.

Rufo was inspired to create Dottie’s after going to college in Boston, and then living in New York City, where she worked at a coffee shop and got to know her community from behind the counter. “You talk to them, you get to know them, they become a major part of your life,” she said. “That became very comforting to me, in my 20s in an enormous city. I started to really see the value in community and how coffee shops bring people together…I started to crave having my own coffee shop and building my own community.”

Around that same time, she decided to move back to the Berkshires, where she grew up hanging out in downtown Great Barrington and Lenox. “It always confused me that Pittsfield was overlooked and underutilized,” she said. “When I thought of places that could use a better sense of community, I instantly thought of Pittsfield.”

As Dottie’s has served tens of thousands of customers (or more) the city has grown and changed, too. In the early days of the business, “it felt like we could make Pittsfield anything we wanted it to be. It seemed to me that if I just opened up something cool, then someone else would open up something cool, then someone else would open up something cool,” says Rufo. “There are ebbs and flows. Right now we’re on an upswing, with lots of new businesses opening downtown.”

The bar at Dorothy's, which offers a happy hour menu.

One of those new businesses is actually Rufo’s new restaurant, Dorothy’s Estaminet, which opened in February. It’s connected to Dottie’s both physically and spiritually. Dottie’s serves a daytime crowd and Dorothy’s is open from 2-9 p.m.; the dining room that connects the spaces is now for both restaurants, allowing customers at both spots to take advantage of more ample seating. It’s been called “the best restaurant in Pittsfield” for its laid-back-French-cafe concept and for its simple menu, which centers around a Mediterranean-style shared plate called “The Experience” that guests can pair with their choice of protein (vegetarian options abound).

“Dorothy’s menu is meant to bring people together in the same way the coffee shop does during the day,” Rufo says. “It’s like this awesome dinner party. You immediately have food to dive into with your people.”

"The Experience" platter, with several sauces, hummus, whipped feta, house pickles, tzatzki, potatoes, pomegranate and other goodies, served with homemade focaccia.

At Dorothy’s, Rufo has also added music, with occasional residencies, including a flagship residency with renowned band Misty Blues, and lots of independent musicians providing evening entertainment.

She says she’s thankful to have such a robust team – not just the kitchen and waitstaff, but also volunteers like artist Richard Britell, who curates monthly art shows at Dottie’s. “When I say ‘we,’ I am first and foremost talking about the people who use Dottie’s as a place to gather,” she says.

Rufo was all-in on downtown Pittsfield before, but post-COVID (when the coffee shop mostly stayed open and also provided some wholesale grocery options for community members in times of need) she’s thinking deeply about how to continue and build upon her work.

“Our community and culture are really suffering from isolation, distraction, numbness, loneliness. I really feel coming together over food and breaking bread, as they say, is the antidote to that,” she says “We just want everyone to come have this experience with us. It’s good nourishing food and a really nourishing experience.”

Rufo particularly loves when someone tells her they know a Dottie or a Dorothy, since she cherished her grandmother and the name means so much to her. “It’s nice to know that name means so much to someone else,” she said. “She adored me and I adored her. I named my business after her because of how she made me feel.”