Robert ‘Bailey’ Stewart remembered for huge heart, witty sense of humor, joy of uplifting spirits of others

Robert “Bailey” Stewart

The Stewart family is deeply saddened to announce the passing of Robert “Bailey” Stewart, son of Walter Alexander Stewart and Audrey Bailey Stewart, and brother to twin Richard “Dick” Stewart, Walter “Buzz” Stewart, and Linda Brockway. Born on July 15, 1943, Bailey was a lifelong resident of New Canaan, a town that was very close to his heart.

While living in the Stewart family home on Hoyt Street, Bailey attended Center School before moving to Gower Road. It was at South School where Bailey met his closest lifelong friends, continually challenging each other with their competitive spirits.

Bailey graduated from the New Canaan High School class of 1961, where he lettered in three sports and won a football State Championship in 1960. At Beloit College, he earned Honorable mention Little-All-American in his sophomore year, All-Conference Offense and Defense his Junior and Senior year, captaining the football team to its best record in 10 years looking back and forward. After graduating from Beloit in 1965, Bailey volunteered to serve in the Army, obtaining the rank of ILT Armor Division.

Bailey met his wife Gail Runyon Stewart in high school, but it wasn’t until he took her on a few motorcycle rides in the fall of 1969 that they finally started dating. Engaged by Christmas Eve of 1970 and married on June 12th, 1971, Gail and Bailey loved to dance together, listen to music, but most of all go out to dinner with their dear friends, where Bailey delighted friends with his impressive story-telling.

Bailey served as President and Chairman of Walter Stewart’s Market and Stewart’s Wine & Spirits for over 45 years, succeeding his father and grandfather Walter Stewart(s). Bailey grew the treasured family-owned supermarket by building a winning culture, while also bolstering community connections.

Bailey served as President of Allied Grocers, a co-op distributing company formed by owners of Connecticut and Massachusetts grocery stores. Bailey had an incredible curiosity, thirst for knowledge, and boundless energy. Bailey earned his MBA from the University of Connecticut in his mid-forties and started two businesses in his mid-seventies – “574 Wine & Spirits” and “Your CBD Store” in Monroe.

Bailey served as President of New Canaan’s Historical Society, Chamber of Commerce, Cemetery Association, and Poinsettia Club. His town government service included Chairman of the Fire Commission, Member of the Parking Commission, Commission to Name the Getabout, and Commission to Furnish & Install the Lou Moreno Clock.

Additionally, he served on the boards of the New Canaan Library, the New Canaan Nature Center, Waveny LifeCare Network, and the New Canaan Bank and Trust Co. In 2022, Bailey was recognized by the New Canaan Community Foundation for his lifelong commitment to public service. He has been honored by the Old Timer’s Association Hall of Fame for his athletic accomplishments and the Gridiron Club for his civic leadership as “Half a Fall Guy”.

Bailey continued his love of sports by playing paddle, tennis and golf, where he spent time with those closest to him. While he enjoyed a good competition, it was the camaraderie that really mattered to him. A lifelong learner, he took his mother’s words to heart, “what did you learn today?”

He was always working on a project, constantly coming up with new ideas to improve his many businesses or perfect ways to tend to his blueberry plants on Blueberry Hill in Block Island. He enjoyed being at the forefront of technology, speaking French, and loved his cars, especially his Tesla. He fancied himself as an artist and could often be found sketching portraits on cocktail napkins.

An avid reader, Bailey could often be found sitting in the New Canaan Library’s newspaper room, reading that day’s paper. He found great peace and happiness in two of his favorite places, Lake Waccabuc and Block Island. Bailey had countless friends and was always making new ones wherever he went. He touched many lives and saw the best in everyone. He inspired all of us with his unwavering generosity, and his passion for living each day in the most positive way.

He will be most remembered for his huge heart, his witty sense of humor, and the joy he felt from uplifting the spirits of all those around him.

“Bebob” adored his grandchildren, Sadie and Sam, and was often heard boasting about their latest accomplishments. He enjoyed attending their field hockey, lacrosse, and football games, as well as any opportunity to give them a ride, captain their friends on boat rides at Lake Waccabuc, beat them at ping pong, or simply exchange stories over family dinners.

Above all, Bailey absolutely cherished his entire family near and far. He loved each and every one of us deeply, supported us endlessly, and was infinitely grateful for every moment he shared with all of us.

Bailey is survived by his loving wife of 51 years, Gail, his daughter Emily Schoonmaker (Phil), his son Jed Stewart, and his grandchildren Sadie and Sam Schoonmaker. He is also survived by his brother Richard, his sister Linda, his sister-in-law Karen,  as well as his much-adored nieces and nephews, grand-nieces and grand-nephews, and the Upton and King families of Massachusetts.

A Memorial Service will be held at 11 a.m. on June 3, 2023, at the Congregational Church of New Canaan, followed by a reception at the New Canaan Historical Society.

In lieu of flowers, please consider making a donation to the New Canaan Historical Society, the New Canaan Community Foundation, or the New Canaan Library.

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