If you’d eaten dinner at the cozy Stockbridge restaurant Once Upon A Table on a warm July, brisk October or cold January evening sometime in the past eight years, it’s likely you were greeted by waitress Avie Maloney. If you go today, in the restaurant’s rebooted form, you’re still likely to be greeted by Avie Maloney, only now she owns the place. She purchased the business in December, and after months of preparation, and a weekend’s successful soft opening behind her, she’s ready to welcome guests to what has become a labor of love. It’s a day 20 years in the making.

Maloney was raised on the Caribbean island of Grenada by her formidable mother, a local Methodist preacher, who worked for a time as the head of the Registry Department for the Grenadian government. Mom had plans for her only child, plans that did not include the “helping” fields, sacrificing to send her to private school to earn a teaching degree. Maloney taught for a while but found she didn’t really take to that work. Via help from her stateside father, and a summer work program at the Red Lion Inn, she made her way to Stockbridge, as a waitress, in 2002. She found she took to the work of “dealing with people.”
She didn’t dare tell her mom about that gig, though. It was only after she’d done a second summer season waitressing in Stockbridge and had returned home to the island that she finally confessed the truth. “I gave her the bad news, that I really like this work. She was like, ‘Are you kidding me? Do you understand what it means to be a waitress?’ At the time I had no idea what she was talking about. It was this historic thing about people of color — which I’m now more educated on — who grow up to be the help. She didn’t want me to be the help, because she worked so hard to be not the help herself … She was upset for a while. She wouldn’t talk to me.”
In 2004, Maloney officially joined the Berkshire hospitality world. She spent the following years as a front office supervisor at Kripalu, then at Blantyre in a similar role, followed by a stint as administrative assistant at Pittsfield’s Center for Eco Technology, pleased to be involved with the recycling movement. “When you’re young, you get excited about all these things.” From there she moved to Berkshire Housing, happy there to be in a position to “help the people in the community.”
She remained at that agency for three years before she found her way both to Once Upon a Table as a waitress, and also to the job she figured her mom could get excited about, at the Montessori School of the Berkshires (MSB) in Lenoxdale. There, until just last month, she was the public face of that small, private school, holding first what she calls the title of “Director of First Impressions,” (aka office manager) and then, more recently, that of Community Engagement Coordinator.
Todd Covert, MSB founder and head of school, says of his former employee, “Avie’s infectious smile and sense of community delighted The Montessori School of the Berkshires for many years. We are happy that she is able to continue delighting others through her own restaurant.”

Nancy Ringer, a parent at MSB for the past 12 years, already misses seeing Avie every day. “What she projects is warmth and welcome. I heard stories of my daughter and her friends sneaking out of the classroom to walk down to her desk to work on their lessons. They just wanted to be in her aura. She’s throwing light at you, she’s so happy to see you.”
This magnetism might begin to explain why today, at a time when most of the work world is having trouble filling vacant jobs, Maloney is suffering from the opposite problem.
“I have too many people wanting to work here!” she lamented.
Once Upon A Table is tucked just off of Main Street in the “Mews,” the narrow alley that runs between Williams and Sons General Store and the old Town Office building that houses Images Photo Galley. The restaurant has a snug indoor seating capacity of 30, rising to 48 with outdoor tables in the warmer months. Opened in 1996 under original owners Lynne and Christian Urbain, the restaurant started serving up New American staples like trout, salmon and lamb for a loyal local and visitor clientele. The Urbains sold the business to Alan and Teresa O’Brient — owners of 7 Arts Gift Shop and Williams and Sons, respectively — just before the turn of the millennium.

This past fall, “physically out of gas” after 22 years at the helm, Alan O’Brient got serious about selling, and, keen to maintain the business’ inviting, community spirit, was intentional about how to go about it. Rather than list it for sale to the highest bidder, he approached his waitstaff. “I really wanted to sell it to somebody who was going to respect the culture … Avie was the perfect person to do it.”
But she had only ever worked as a helper. Business ownership? This was a whole different animal. To both her and her partner, who’d recently been laid off and was trying to make of go of it on his own, buying a restaurant felt very much like jumping off a cliff. “I’ve never not had a job. Yesterday I had to get my teeth cleaned, and I was like, ‘Oh, do I have dental coverage?’ I never had to think about that stuff because we always had that covered.”
A big support team has her back. Last fall, a mutual friend reached out to local chef Alex Chisholm, who had been spending COVID living a nomad’s life, traveling around the U.S. in a van with her husband, picking up cooking gigs as she found them. “I was planning to stay in Florida,” Chisholm said, “where I was visiting my grandma. We were not really thinking we’d come back to the Berkshires. But then I got the call about Avie and the restaurant. I always loved the location and daydreamed about that spot. I’ve been so enchanted by it. We moved back here in December, specifically for me to take that job.”

Maloney has empowered Chisholm to select the menu, which features both comfort staples like mac and cheese and American fine dining classics that will change frequently, with all menu items emphasizing local growers and products. “What I did tell Alex,” Maloney explained, “is I want to support local, and I told her what people came for. I want to keep things similar, but give them a little love, and a little updating.” Much of the restaurant’s ingredients are sourced by eight local providers, including Tyringham’s Woven Roots Farm.
Woven Roots owner Jen Salinetti has by necessity been focusing her efforts on direct food access, as opposed to provisioning restaurants, but in the case of Once Upon A Table’s new ownership, she’s made an exception. “Our demand is greater than what we can supply. We’re building this in, because it’s Avie. I’m excited to see her emerge into a place of leadership where she has been involved for so long in customer service and community care.”
Stockbridge resident and longtime Once Upon A Table customer Sandy Newman, founding director of Community Access to the Arts, is pleased with the change, and looking forward to seeing what Maloney does. “I’ve always been so appreciative of having the restaurant there, and when I heard that Avie had bought it, I thought that was a wonderful thing for the whole community. She was always very caring, and fun to be with. She knew exactly what I was going to order. She’s just an open and giving person, and I think it’s a true gift to the community and the Berkshires to have somebody like that buy it.”

Another word that naturally attaches to Avie Maloney is community, to which her new iteration of Once Upon A Table is a testament. The floors were restored to their original shine by a former Montessori colleague. Her waitstaff is headed up by her longtime colleague at the restaurant, and also includes two former Montessori colleagues. Website photos? Taken by a Montessori parent. The shelves? Built by another. The plumbing was brought up to code by a former Blantyre colleague. A friend’s son washes dishes. Mary Sipp Green, loyal Once Upon A Table customer, is the featured artist whose paintings grace the walls.
“I’ve never worked for someone as loved as Avie,” said Chef Chisholm. “Someone would show up, saying, ‘I want to participate in this way.’ Everything you see here is people who love Avie. It’s a village coming through to pull this together and support her. I’ve never seen anything like it.”
For the time being, the restaurant’s hours will be Thursday through Monday, 4–8:30 p.m., with the addition of lunch likely to begin around Memorial Day.
Maloney also has ambitions for community events like “pop-up nights” to showcase local international chefs and home cooks. Perhaps an evening of Asian cuisine, another of Italian, with wine pairings, or a Grenada-themed event. “I want to do that in the winter months, for the locals. I feel that the locals get overlooked. Maybe we’ll have a service night, for servicepeople.”
Taking a moment to reflect on the winding path she walked to reach it, Maloney said, “I didn’t know that all of this stuff was leading me to this point. Waitressing was a stepping-stone. I just want to be Avie, who has proven her mom wrong, by making her proud.”
