This is how the conversation generally goes: “Oh, you’re from Windsor? Do you know…”

“Yes,” I cut the inquirer off, jokingly. It’s often a favourite babysitter, a former neighbour, or one of my mother’s mah-jong partners. That’s just what it’s like growing up small-town Jewish.

Things came full circle for me recently at Windsor’s first Jewish community reunion. Close to 400 people crowded into the city’s JCC, the epicentre of Jewish life in the city since it opened in the late 1950s, for an epic homecoming.

“It was one ‘OMG’ moment after another,” says reunion co-chair Karen Rosenbaum Moness. “Some people hadn’t seen each other in 40-plus years!”

Guests ranged in age from 19 to the mid-90s, and came from as far away as British Columbia, New York, Florida  and even Hong Kong. “We reconnected not only with family and friends, but also with friends of our parents and grandparents, former Hebrew school teachers, day camp counsellors – people who really made a difference in our lives,” adds Karen’s childhood friend and reunion co-chair, Amy Whiteman Shafron.

At 95, Sam Orechkin was the evening’s oldest attendee. Sam, who worked for his father transporting cattle to local butchers, left Windsor in the 1940s (he currently lives in Detroit) but still feels a connection after all these years. At the reunion, his daughter, Lisa, later told me, “he would see someone’s name tag and ask ‘Who was your father? Who was your grandfather?’

“He had such a great time.”

For Alan Orman and his wife Diana, pillars of the Jewish community for the past 60 years, the reunion was simply too important to miss, despite Alan’s recent stroke.

“Life changes on a dime,” says Diana,  “but we certainly were blessed that Alan was able to attend this incredible event.”

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Meanwhile, Mikie Freed, a longtime Windsor resident and philanthropist (and one of my mom’s mah-jong partners) said the best part was seeing her childrens’ friends all grown up, successful, with families of their own. Janet Cohen Rosenbaum, 82, was thrilled to reunite with many of her childhood friends who came in from Boston, Ohio and Michigan. “It was as if time stood still and we were teenagers again!”

From Hadassah bazaars and elaborate Jewish theatre productions to B’nai Brith championship bowling leagues and cross-border youth groups, there’s no question Windsor was – and is –  a special place to grow up Jewish.

“A favourite for me was going with my grandmother to do the shopping for Shabbat,” remembers Naomi Weinroth. “We would go to the market, to Adler’s and to Hy’s fish market and Harry the butcher. Harry always had an Elite flake chocolate bar to give me while my grandmother ordered the meat.”

For Carrie Winograd Kaufman, who flew in from New York, one of her favourite memories is attending Camp Yomee at the Windsor JCC, especially the friendship circle song they’d sing at the close of each day. “Friends, friends, friends, we will always be…”

One of my favourite traditions was accompanying my Bubbe Esther on Rosh Hashanah to perform tashlikh, casting our sins – bread crumbs – into the murky water of the Detroit River. People would stare in wonder and I would feel proud, even though I didn’t really know why. One of my not-so-favourite memories is dodging the many single suitors Bubbe would invite to her apartment for Shabbat brunch. “I want you should get married before I die,” she would say in her Yiddish accent. “And I don’t feel good.” (It’s all about the comedic timing with Bubbe E.)

According to the late Rabbi Jonathan Plaut, author of Windsor’s Jews: 1790 to 1990 (and a former neighbour), the city’s Jewish population reached 3,000 in the 1930s and early 1940s and remained steady right up until the 1980s. Since then, however, the numbers have shrunk significantly – down to 1,500, with half of the members over the age of 60.

“The Windsor Jewish community has always been small but mighty,” says Jay Katz, executive director of the Windsor JCC. “Nothing demonstrates that more than hundreds of people flying in from North America and across the world to spend a night laughing, smiling, hugging and reminiscing with old friends, about the warm joyful experience they had growing up in Windsor.”

Katz says that, despite the challenges, it’s a good time to be Jewish in Windsor. The JCC’s membership is on the rise, a generous endowment fund is supporting long-standing infrastructure projects and innovative partnerships with local school boards, the Windsor Police Service and even the government of Mexico are helping to raise the organization’s profile.

Proceeds from the reunion will be used to “pay it forward” to the Jewish community. “Our goal was to ensure that we covered our costs of the event with the added benefit of any surplus remaining in the community’s endowment,” says Rosenbaum Moness.

The evening was also an opportunity for Jewish Windsorites of all ages to come together and celebrate a shared history. “The theme of the reunion – ‘There’s No Place Like Home’ – could not have been more fitting,” Rosenbaum Moness adds.

“The connection we have and the love that we share for one another and our community is very special,” says Whiteman Shafron. “I don’t think you find that in many other small cities.”