BROUGHT TO YOU BY
ONCE UPON A TABLE
In the American imagination Main Street in Stockbridge is one of the most evocative stretches of road in New England, thanks to the 1967 Norman Rockwell painting of its Christmas iteration.
Stately, sprawling Red Lion Inn anchors the western end of its main stretch and a line of colonial-era storefronts runs east. You can’t see it from the road or in the painting, but tucked into a narrow alley between old town offices and general store is a charming little restaurant. It’s called Once Upon a Table (OUAT), has just twenty-eight seats, and the owner who greets you has a very modern American success story.
Avie Maloney has owned OUAT for five years and this fall, she says, she’s in a “Thank you” mood. 2026 was the first year she felt secure enough in the business to close for the off-season, meaning the month of March, to visit her mom back home. That fact alone tells a story about how far she’s come.
Once upon a time, Avie left her home island of Grenada and arrived in the US for a job at the Red Lion. She eventually joined the administrative team at the Montessori School of the Berkshires as the welcoming face of the front office, while also waiting tables part-time for then-OUAT owner Alan O’Brient at the establishment she’d one day own.
“I was the one he could call and say, ‘Hey, somebody’s sick, you want to come cover?’” she says of O’Brient.
In 2021 O’Brient was ready to sell. Maloney wanted to buy, but it would be stretch to claim she was ready. It was still the COVID era, and banks weren’t financing restaurants. But she decided to be seize the day, and made an offer she expected to be refused.
“I said to him, ‘I want to do this, but I don’t have the money, and the bank is not giving me any money.” She asked for a deal that would bypass the bank. “I was waiting for him to say no. I was going to go back and live my life.”
But he said yes. Five years later, she still writes a check every month not to a bank, but to her former boss who believed in her.
“Who does that?” she says.
Once it was hers to take care of, people came out of the woodwork, or rather her Montessori rolodex, to help. A former colleague knew a retired restaurateur who showed her how to build spreadsheets and ask for funding. Another came out of retirement to do the books. A Montessori parent/ carpenter [full disclosure: my husband, Jim Clary] renovated the place, and has been called back into service each year since. Small start-up investors, many of them school parents, put up money. The waitstaff were former students.
When Maloney opened, the cozy dining room looked like a school-based party.
“The first month or two, it was all Montessori,” she says.
But while there was ample support and cheerleading, the first several years were still very hard. If you were to check out the national stats on restaurant start-ups, you’d learn that less than half of them make it through two years. In Maloney’s first two years three chefs came and went, invoices got lost as upstairs office space turned into storage, and the kitchen floor had to come up entirely when a repair turned into a replacement, among other crises. For a long time it seemed like money was only going out, not in. It took until last winter before she could keep ahead of costs and look at actual income.
Near her desk she keeps the close-of-day report from the worst night, when receipts were in the low double digits. She’s sure to look at that report during the boom time in July.
“It reminds me why every phone call and email is important.”
Winter, in other words, is always coming.
What she’s looking to do now is to build up OUAT’s small winter events — holiday parties and the like - to carry the restaurant through the slow months. She’s also busy as vice president of the Stockbridge Chamber of Commerce, but though she’s been asked to serve on various other committees, that’s the only outside commitment she’s committed to. She doesn’t want to take on more than she can responsibly handle.
Maloney is ready to center gratitude these days because she knows it isn’t easy for people to prioritize a nice dinner out right now. Gas prices are keeping people closer to home. It requires discretionary income. Given the hard times she appreciates each and every customer, especially the regulars she counts as family. Hotels and bnbs send guests her way. She recalled the rabbis who noticed the mezuzah she’d been gifted but which had been hung up incorrectly on the door jamb, who later returned to not only affix it properly but to hold a ceremony right there at the threshold to bless her restaurant.
“I can’t do it without the people. The people making the reservations, the people showing up, the people giving us reviews. Word of mouth goes a long way….This is a story about relationships, and trust.”
Wonderful article Sheela! Congratulations Avie! You're the best and we love you and OUAT!