[This is the first installment in a four-part series “Matriarchs of Main & Elm,” profiling the women behind New Canaan’s great business families.]
Audrey Bailey Stewart had recently married Walter Stewart, Sr. when the young couple moved in with her husband’s parents—Walter Stewart, who had founded his eponymous food market on Main Street in 1907 and his rather formidable wife, Nellie, New Canaan’s first woman elected to the state legislature—at the Hoyt Street home that’s still in the family.
A smart, strong-willed woman in her own right, Audrey didn’t always have an easy time living with the in-laws and “she didn’t always get along with Nellie,” family historian Karen Brockway Izzo said, recalling one funny story from her grandmother.
“Once, Nellie told her that she didn’t like the color purple,” Izzo recalled. “Grandmother apparently had a bit of a rebellious streak, and after a disagreement, painted her entire apartment purple. Even the bathroom.”
After meeting her would-be husband through a chance encounter after taking in a movie at the (then relatively new) New Canaan Playhouse on Elm Street while still a teenager, Audrey Stewart would go on to immerse herself in one of the town’s most important and civic-minded business families.
From humble beginnings and acquainted with tragedy even as a young girl, Audrey Stewart would go on to forge a definitive and direct positive impact on the family business during a crucial period of growth, while rearing and raising an entire generation of Stewarts well known to locals.
Born on Oct. 22, 1920 in Pound Ridge, N.Y. she grew up Audrey Bailey in White Plains with her parents, older sister Jean and younger brother George. Audrey enjoyed horseback riding with her sister, and her favorite book was The Secret Garden by Frances Hodgson Burnett, a story of a young girl whose tragic circumstances teach her how to love and to overcome adversity.
The book would come to resonate with Audrey in ways she could not have imagined.
According to Karen Brockway Izzo, 10-year-old Audrey witnessed her own cousin’s drowning, a horror that gave way to a lifelong fear of water. Some years later, her teenage brother George ran away to join the Royal Canadian Air Force (he was too young to join its counterpart in the United States), and he was killed in his early-20s when his plane was shot down over Berlin.
Today’s generation of Stewarts are very familiar with the family stories surrounding Audrey, and Doug Stewart, a 1994 New Canaan High School graduate, named his middle child after his grandmother.
“It was a way to honor our grandmother, also a middle child,” Stewart said on a recent afternoon amid the bustling backdrop of shoppers picking up seasonal produce.
Added older brother and colleague Alex: “And a great opportunity to use another family name.” (Alex has a son named ‘George.’)
The brothers spoke from the upper Elm Street location that most New Canaanites have always associated with Walter Stewart’s Market. However, at the time of the move up from Main Street—1957—it was far from a sure thing.
The first Walter Stewart, an enterprising young grocer from Ireland, opened the first, small grocery store on Main Street opposite New Canaan Town Hall in 1907. His son (Audrey’s husband) became proprietor in 1933, and nearly 25 years into his stewardship, Audrey was a key influence in the decision to expand the business to a new, much larger location. Now, 58 years later, the family is expanding again, as Stewarts Spirits moves into a new space on an adjacent lot and the market boosts its fresh seafood and meats, hot-foods bar, salad bar, local and organic produce offerings.
Audrey embodied a nimble sense of entrepreneurship that made her an asset as her husband’s business partner, her son Richard Stewart recalled.
Once, when the four Stewart kids were very young—say between nine and 12 years old—their father ended up owning a lakeside cottage in Pound Ridge after he loaned a butcher $8,000, took the mortgage on the property on as collateral, and the butcher skipped out.
“Audrey never whined, complained, looked back or felt sorry—she always took charge and forged forward to a solution,” Richard recalled. “She had all of us sanding, priming and re-painting that house’s interior and cleaning up outside that weekend. Then she put it on the market just days afterward. It sold quickly because of its new sparkle, and what could have been a disastrous loss back then—$8,000 was a lot of money for a struggling young grocer—turned out to be a quick flip with no loss.”
She may never have met Walter Stewart, Sr. if not for an apparent oversight by her big sister, Jean.
As Doug Stewart recalled, reciting another family story, both Bailey girls were teens when Jean drove Audrey to the movies on Elm Street, and was supposed to pick her up after the film ended.
When it was clear that Jean would not be retrieving her from the theater, Audrey began to walk up Elm Street. A young Walt Stewart, Sr. spotted her and offered her a ride. The chance timing of a big sister’s error coupled with an astute eye for beauty paved the way for decades of Stewarts in New Canaan.
The young couple eloped in Maryland on May 5, 1940, and then returned to New Canaan to help run the market and to raise four children: Linda, Walter Jr., Robert (known to many as ‘Bailey’) and Richard.
Her kids remember their mother—who served as vice president and secretary of the Walter Stewart Company—as totally committed to making the market a welcoming place.
She launched a popular practice whereby every Friday night, she and Walt would open the market doors to host free coffee gatherings, together with close friends Ray and Ginnie Fairty.
Richard recalls that he and his brother Bailey would pack groceries until 9 p.m. on those Friday nights, and that Audrey exerted a strong influence on all of their childhood friends.
“She was a no-nonsense mother of us, but also of our friends,” he recalled. “Our house was the focal point for all of our friends, who were always welcomed, and always treated like family. Which often meant that when they walked in the house they were quickly instructed to take out the garbage, or instantly do some other task. They obeyed, and never dared to complain.”
He continued: “Years later, when those young boys who lived in the neighborhood had grown way into adulthood and were parents themselves, they universally said they were in awe of Audrey Stewart and loved her like a second mother.”
Her sense of community extended well beyond family and friends.
In addition to her roles of mother, wife and business partner, Audrey was a Cub Scout den mother, docent at the New Canaan Historical Society and a founding board member of the New Canaan YMCA. An education from The Katherine Gibbs School in her back pocket, she worked for a time as a secretary at Merrill Lynch and was deeply involved with the Thrift Shop on Locust Avenue.
One of the Stewarts, Audrey’s granddaughter Sara Brockway Cohen, credits her grandmother with instilling a strong work ethic through “all that time spent with (Audrey) in the thrift shop sweeping and cleaning and organizing and sorting under her guidance.”
Though she passed away in September 1993 at age 72, Audrey Bailey Stewart’s inspiring spirit radiates through her extensive family.
Steeped in tradition with many members remaining on the board of The Walter Stewart Company, as well as still living in New Canaan and attending New Canaan Public Schools, the family regularly recalls Audrey Bailey Stewart—beloved mother, grandmother and great-grandmother, and matriarch behind the market.
Stewart family members still residing locally are:
- Robert Bailey Stewart (third-generation Stewart), Alex Stewart (fourth-generation), and Doug Stewart (fourth-generation) work for the family business and live in town with their respective families.
- Robert Bailey Stewart and his wife Gail Stewart (serves on Walter Stewart’s Board) live in New Canaan.
- Alex Stewart and his family (wife Suzy, son George (Saxe middle school), daughter Meg (South School) live on Hoyt Street in the house originally owned by the first Walter Stewart.
- Doug Stewart and family (wife Julia, daughter Scarlett (South School), Audrey (First Presbyterian Nursery School), Griffin (19 months) live in New Canaan.
- Emily Stewart Schoonmaker (serves on Walter Stewart’s Board) and her family live in New Canaan (husband Phil, daughter Sadie—at Saxe), son Sam (South).
- Patricia Stewart (Alex and Doug’s mom) lives in New Canaan.
- Karen Stewart (wife of Walter A. Stewart, Jr., who passed away earlier this year) lives in New Canaan.
- Richard Stewart (third-generation Stewart, serves on Walter Stewart’s Board) lives in North Salem.
- Jenna Stewart Overbeck lives in Darien (with husband Scott Overbeck, sons Graydon, Rhys and daughters Merryn, Ellery and Tierney).
- Linda Stewart Brockway (third generation, serves on Walter Stewart’s Board, lives in Florida with husband Bob).
The rest of the Stewart cousins and family live elsewhere, including Maryland, Boston, North Carolina, Colorado, California and Washington.