Jessica Stewart was born a child of privilege in Middlebury and used that privilege to greatly enrich her home community. In her long life she brought together some of the most prominent family lineages in Middlebury history — Seymours, Battells, Stewarts and Swifts — adding to their achievements her own record of persistence, cosmopolitanism and significant philanthropy. Transcending the bounds of the conventional role her family had ordained for her, she independently exercised a sense of responsibility to others and helped shape the Middlebury we know.
She and her twin brother (who died at the age of 10) were the youngest children of the honorable John W. Stewart, banker and businessman, Vermont legislator and governor, and then U.S. representative and senator. Her mother, Emma Battell Stewart, was wheelchair bound from the time of Jessica’s birth and unable to follow her husband in his political pursuits beyond Middlebury. Instead Stewart relied on Jessica as his indispensable companion on travels abroad, where she studied voice and piano in Europe, and as his shrewd hostess in Washington, D.C., through three presidential administrations. 
Her father’s dependence on her presence led to roadblocks in her personal life. In her late 20s she met and fell in love with New Hampshire cleric Joseph Walter Sylvester, but her father forbade their marriage on the purported grounds of Sylvester’s inferior social status. In spite of paternal opposition, she maintained the relationship for eight years through correspondence and rare visits. Learning that Sylvester was dying of consumption, she eloped with him in the fall of 1908 and nursed him through the last eight months of his life before returning to Middlebury and her father’s dominance. 
She married again in 1913, this time to an “acceptable” partner, Charles May Swift, resident in Michigan, where he had made a fortune in railroading and mining, but also descendant of the distinguished Middlebury family that had built what had become the Stewart family home (now the Swift House Inn). Jessica’s father’s needs, however, required her frequent returns to Middlebury in the subsequent two years before his death. Thereafter the Swifts maintained a base in Grosse Point, Michigan, summer homes in Middlebury and on Lake Champlain, and a winter apartment in New York City. They traveled widely, including an adventuresome period in the Philippines, where Swift founded and built electric utilities and street railways. Falling ill in 1929, Charles Swift withdrew his assets from the markets and preserved them in trust for his wife, dying just before the crash of that year.
For the next decade Jessica retained the New York apartment and summered in Vermont, honoring her ties to Middlebury (where she returned permanently in 1939) and undertaking what would be half a century of philanthropy and local support. She was involved in the 1927 purchase, rehabilitation and rebirth of the Addison House as the Middlebury Inn. In 1932 she donated to the Town of Middlebury the house her great-grandfather had built and endowed it for use as a Community House, with a special emphasis on children’s welfare and activities. She built a relationship with Sir Wilfred Grenville, who had retired to Charlotte in 1931, and became a major supporter of the Grenfell Labrador Mission. She sponsored charity events for the Mission at New York’s Carnegie Hall, hosted a tearoom in her Middlebury home as an outlet for Grenfell’s Labrador craft industries, and ultimately supported the 1936 opening of the Dog Team Tavern in New Haven as an American outlet for the Mission. In the 1950s she paid for refurbishing the spire of the Congregational Church. In the 1970s she underwrote the construction of the Stewart-Swift Research Center at the Sheldon Museum, an institution with which she had had a significant interest since the days early in the 20th century when she had facilitated conversations between the two deaf friends Henry Sheldon and her uncle, Joseph Battell. 
Wintering in her last years in Florida, she remained a temperate-weather presence in Middlebury, known familiarly as the town’s “Aunt Jessica.” In 1981 she was cited by the “Guinness Book of World Records” as the oldest living person (at 110) to be a passenger on a plane. She died in 1982. At 110 years and 107 days, she was cited as having been the oldest person ever to be born in the State of Vermont. The record of her long and eventful life is preserved in letters and documents that she and her heirs have donated to the museum’s archives. A 1975 interview with Jessica Swift can be heard on the Archives page on the Henry Sheldon Museum website at henrysheldonmuseum.org/audio-recordings.
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Contributed by the Research Center Committee of the Henry Sheldon Museum. Excellent as the Research Center documentation is, it doesn’t include everyone. Which courageous women of the past come to your mind? Who deserves recognition for their part in surviving or driving change? Why? Would you tell us about them? What about the Abenaki and people of color who’ve been ever present but little recognized? Do you have stories about them? We’d love to hear from you. Please get in touch at [email protected].