Bear Guidry will head off to school to start the academic year on ThursdayAug.31, just like hundreds of other young students around the district. Bear will be beginning his student career at Holmes school, again like many other students eager for a new school year. Bear however, is part of a legacy that is as  special as any piece of history in Darien. Bear will be the sixth generation of his family to attend Holmes, the family reaching all the way back to the late 1800s.

Chinkara Guidry and her son Bear, the sixth generation of his family to attend Holmes SchoolBear’s mother, Chinkara Singh-Guidry, was a student at Holmes in the 80s, and her mother, Dana Arnold, was also a student at Holmes in the 50s. Arnold’s mother, Vivian Woolley-Arnold but going by Debi, was a student at Holmes as well, and went on to teach kindergarten at Holmes for 25 years. Debi actually had Chinkara as a student during her time there. Members of the Holmes School staff still fondly remember Debi, and a trip through the school’s social media pages reveals a trove of kind words and photos.

Debi’s mother, Esther Carlson Woolley, attended Holmes when it was on the corner of Middlesex and Hoyt Street, and that was in the late 1890s. Her family lived on the corner of Noroton Ave and Oak Street, simply called “The Heights”. Esther was one of the women responsible for the creation of Troop 383, which at the time drew girls from Stamford and Darien as the first troop of girl scouts in Darien.

“We grew up on Phillips Lane, where my grandfather and great-grandfather built a house,” said Chinkara, who happily remembers walking to Holmes School as a young student. “We’re making a lot of new memories now as Darien changes,” she added.

When she thinks about her son, Bear, attending, it’s incredibly exciting.

“To know my son will go to Holmes and do the same things I did, it’s really fun to think about,” Chinkara said. “The gym is the same as when I went, so is the library, so there’s a lot of comfort,” she added.

Chinkara and her mother, Dana Arnold, both remember a lot about their youth in Darien.

“Where we grew up it hasn’t really changed much. Palmer’s, the shopping center,” said Chinkara, adding the train station was an addition they spoke about sort of tongue in-cheek, clearly preferring it not go up next to their childhood home, but otherwise Arnold and Singh-Guidry spoke glowingly about Darien.

“We of course felt Holmes was the best school in Darien,” said Chinkara.

“It’s very comforting to know my son is going to Holmes. Living on West Avenue, growing up on Oak Street, it makes me very happy,” Chinkara added.

A town like Darien will always have its share of history and legacy. The town itself was incorporated in 1820, and has no shortage of historical landmarks. The Stephen Mather home recently became a museum itself, well worth a visit to take in a piece of living Darien history. But the ability of one family to trace six generations of attendance through a single school is special. Time passes in Darien, the town changes, people come and go or move around within town, so one family being close enough to the same elementary school for about 120 years is a unique way to mark the time.