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In 2004, I wrote a magazine feature for Toronto Life on the town where I grew up, Oakville, a posh, terribly Anglo suburb of that city. The magazine was regularly running features on neighborhoods — mainly within the city — then. But Oakville was sort of honorary Toronto Life territory — as aspirational as the magazine. It appeared in the magazine with Peter Sellar’s super photos enlivening the text.


Quaint, picturesque and at a safe remove from big-city ills, Old Oakville is the perfect place to grow up. Meeting the town’s expectations, however, is another matter.

Old Oakville is a place where people who’ve made it go. You can imagine it, even if you’ve never driven the half-hour on the QEW to see it. The Victorian homes have shutters on the windows and historical society plaques near the doors (Capt. William Wilson, Mariner, 1862). Mature maples and oaks shade the streets. The parks are filled with bandstands and war memorials. In the summer months, the harbour echoes with the sounds of dinging masts. And every Sunday, church bells chime out hymns — “All People That on Earth Do Dwell,” “O Come, O Come, Emmanuel.” Oakville is exquisite in its way, if a little too too.

I grew up here and left to go to university in the mid-’80s. Since then, I’ve lived abroad (England, Ireland and the United States) and, for the past decade, in Toronto. As I look back, the town that we, its children, once accepted unquestioningly as normal, seems odd, almost exotic. A family we knew once acted out Macbeth on their lawn — with their youngest relishing his cameo as the boy prince who gets slaughtered by the protagonist. At a croquet party hosted by a former resident, one-time Globe and Mail editor Norman Webster, the guests had signs affixed to their backs displaying literary quotations of famous couples: men got Antony, Napoleon or Samson quotes, women got Cleopatra, Josephine or Delilah. The guests then had to ask one another for clues about their assigned identities, locate their other half, then compete together in the ensuing tourney. Every Sunday, comb-wielding church ladies used to dress us, the boys’ choir of St. Jude’s Anglican, in blue cassocks, white surplices and star-pleated collars.

Like most small-town denizens, I loved the intimacy as a boy, puttering safely about the leafy old streets. And I loathed it as an adolescent, escaping on the QEW every chance I got. But unlike the Thornhills and Markhams and Streetsvilles of southern Ontario, Oakville is a special case. It’s become a suburb of Toronto, but has kept its small-town mentality; its singular sense of place has remained intact. One of the last enduring haunts of the Anglo, Oakville reeks of perfection.

Upon his retirement [from shipbuilding and sailing], Captain Andrew continued to live with his sisters at No. 5 William Street, where they had moved in 1891 … A day never passed without Captain Andrew and his dog walking several times down Navy Street to view the lake and the harbor. — Oakville and the Sixteen

This quote from Hazel Chisholm Mathews municipal history gives a flavour of the life that, for many years, prevailed in the town’s oldest district. Life here has proceeded at the same pace for a long time, that is to say, slowly, decorously. One of the directors of the historical society, an English-accented former research chemist named Harry Buxton, calls what Oakville offered its settlers, and what it continues to offer its inhabitants, “a vision of gracious living.” In Old Oakville’s houses, family portraits still stare out from dining-room walls, and pianos yet inhabit pride of place in the chesterfield-filled parlours — even though the children prefer the televisions and computers that have gained a foothold on the upper storeys. Front doors are still sometimes left unlocked during the day. In the evenings, hospitable candles light many windows. At the end of a dinner party, you can expect to be seen out in the old style, with the host and hostess on the porch waving to your departing car.

The village of Oakville was founded here in the 1820s by Mathews’ forebear, William Chisholm, a veteran of the War of 1812 whose Loyalist family had fled the American Revolution. With proceeds from his general store, Chisholm bought 960 acres around the mouth of the Sixteen Mile Creek, dredged the harbour and began to advertise for settlers. From the start, he aimed to attract the right sort by making the sale of land plots conditional on the buyer’s agreement to build within 18 months “a stone, brick or frame house, not less than 24 feet by 18.” An active historical society has ensured that many of those houses are still extant. (There are more heritage buildings here than in any other Ontario town.)

It’s from this hub, roughly a square kilometer north of Lake Ontario and east of the Sixteen Mile Creek, that the modern suburb of 150,000 people sprawled. This sleepy residential district once functioned as an active port, filled with granaries and shipbuilding workshops, producing the leaders and setting the tone for the larger municipality. For many years, the town felt smugly superior, secure in the knowledge that it was one of the jewels in the British North American crown. Now, the downtown core is surrounded by more populous post-war subdivisions, and its patrician-aspiring residents no longer dominate the town council. Still, when people talk about Oakville, it’s usually Old Oakville to which they are referring.

On the banks of the Sixteen Mile Creek sits one of the town’s tony institutions, the racquet-playing and yachting Oakville Club. As a member, you have signing privileges in other gentry-filled clubs across the country, in Westmount and West Van, in Toronto and Calgary. I remember my first tennis lesson here. With all of us assembled in the requisite whites, collared shirts only, the pro began by laying out the game’s etiquette: no running behind the courts; if your ball goes on the next court, politely ask the players to return it — when there’s a pause in their play. In Oakville, the raucous or even slightly risque sticks out, which explains my vivid memories of our salty-tongued badminton coach taking not so discreet sips of beer between points, or of my mother, in a fiercely fought tennis final, losing her wrap-around skirt mid-point. In front of the many spectators, she gamely finished the rally in her bloomers.

The houses in Old Oakville are surrounded by meticulously maintained gardens. In the run-up to Christmas, the rhododendrons are wrapped, and bushy wreaths bedeck the homes (sometimes every window). Growing up here, I told time by the church bells. Afternoons would disappear gossiping with a British ex-pat mother of five in her ivy-covered bungalow or with a World War I vet as he clipped his lawn with a manual mower. It was sociable and drop-in friendly — or so it seemed to me then.

The sisters at the nunnery next to the Catholic church often protected one of their local favourites, a kid wanted by the police for driving an unlicensed go-kart. He would beetle into the nunnery yard, then close and lock the gate. The constables, in hot pursuit, would knock on the nunnery door, and without hesitation, the sisters would ask whether they’d brought a warrant. Maybe it’s apocryphal, but the story gives a sense of how protected we felt — there was always someone watching over us.

And yet prolonged exposure to Oakville, with its many near perfections, has a way of making you feel inadequate. By my age, I should have the following to my name: a car, a wife, kids, a home, a cottage and a 30-foot-plus yacht, a craft I would describe, with faux modesty, as my dinghy. If I’d learned my lessons well here, I most certainly would not have turned out gay.

Oakville has an uneasy relationship with life’s vicissitudes — people will often skip town after a divorce or business set-back, seldom to be heard from again. In the ’80s, one of my teachers clubbed his family with an axe and then hanged himself; a local woman recently sent an open letter to her church’s congregation detailing her husband’s alleged infidelities; accusations of sexual abuse once rocked the local private school, Appleby. Here, as everywhere, bad things happen to good people. But the big and small unpleasantnesses have a way of swiftly leaving the local consciousness, like so many ugly but minor contretemps in this otherwise marvellous existence. There is no misery like the misery experienced in such a perky, upbeat place.

Any woman who tells the truth about herself is a feminist – Alice Munro

The Oakville of my youth wasn’t all about the cheerful, the stoic, the denial of difficulties, though. As in many commuter towns, Oakville’s ethos was defined by its full-time residents, its women. There was a tradition here like the one E.M. Forster evoked in Howard’s End, of one woman passing on her love of this particular corner of the world to the next generation. When our young family moved into a home on William Street in 1969, the widow who sold it to us left a horseshoe nailed above the door, so that it formed a U above the frame. “Keeps the luck in that way,” she told my mother. Another long-time resident shared with my mother the secret location of a wild asparagus patch. Small gestures, but pretty ones.

Whenever extraordinary people — and many of the town’s women were that — lack obvious outlets for their energies, they find ways to contribute. When I was in middle school, three overqualified local mothers taught a few of us an enrichment class one morning a week. All three had done graduate work, and rather than participating in the cut-and-thrust of high-level academic life, here they were instructing a bunch of 10-year-olds. They had us sculpting islands out of papier maché, and imagining the civilizations that populated these archipelagoes. Other women taught immigrants to speak English, squeezed thousands of pints of blood out of fellow Oakvillians and found homes for stray animals. “Reach higher,” one of the women who played badminton at the Oakville Club used to tell me.

It was the ’70s, and the town was coming to terms with feminism’s so-called first wave. The more progressive women of Oakville were tired of serving as hostesses in the evenings, spending their days taxiing their kids from sports meets to music lessons. In the year since I left a quiet revolution has taken place. After raising their children, many members of my mother’s generation went to work. A few returned to school and entered the professions; others launched retail enterprises on the main street. One of the largest independent mail-order companies in the country, the Added Touch, was founded by entrepreneurial Oakville women with, at last, a bit of time on their hands. Some of them became the first women in their well-heeled families’ recorded history to secure paid employment outside the home. Perhaps it wasn’t the fiercest blow feminism ever deal the status quo, but it was progress nonetheless.

The town has had a female mayor for the past 15 years, and no one, least of all Ann Mulvale, views this as remarkable. “When I started running for council in the late ’70s, there were still questions like “if you win, who will take care of your family?'” she says in a gravelly voice. “One of the greatest compliments I get now is that people speak to me as genderless.”

In the last two or three years, the millionaire element of Toronto has become acquainted with the idealities of this nearby community, and in that brief space they have hustled themselves to that spot like leisure-loving Europeans to the sunny Riviera – Toronto World, 1910

In the early years of the 20th century, a few real magnates — the upper half of the other half — discovered Oakville. If the houses in Old Oakville resemble so many parsonages out of Austen, the grand homes that line the lake farther east have a Gatsby ethos. For about a kilometer past the downtown, you’ll find the ivy-covered estates of yesterday’s tycoons: the meat-packing Morrison Brothers’ Gothic Revival manse and stockbroker James Gairdner’s former abode, now the art gallery and rose-filled park, Gairloch Gardens. Back in the day, an Eaton built here, as did Birks’ former head, James Ryrie. This infusion of wealth, along with the Ford Motor Company’s decision in the ’50s to locate an assembly plant up near the highway, has made the town a perennial contender for the title of richest municipality in Canada.

Some newer, brasher titans have recently followed their predecessors’ lead. In the late 1990s, Microsoft Canada president Frank Clegg tore down the old Eaton pile, Ballymena, and substituted a castle that looks like a restrained product of King Ludwig’s megalomania — if such a condition could countenance restraint. Not to be outdone, Interbrew’s former chief, Hugo Powell, is currently constructing what will be one of the largest homes in Canada. When completed, Powell’s pad, the absurdly named Chelster Hall, will feature 54,000 square feet of floor space, and the 10-acre lot will boast such amenities as a tennis pavilion, a boathouse and a private chapel. The aesthetic of these newcomers is unashamedly Assyrian: they aim to awe.

These houses signal Oakville’s move to another echelon of richness. Where station wagons once careened along the streets, nowadays there’s a veritable fleet of Saabs and BMWs, of Land Rovers and Mercedes SUVs. And the business district features a more exclusive breed of shop. On the six blocks of Lakeshore Road East that constitute Oakville’s downtown, there are two pet-care emporia (Burberry carrying cases, “cakes for birthdays and other pet occasions”); many wealth-managing financial planners and banks; a furrier; numerous bed, bath and garden outfitters; gourmet groceries; a colonial outpost of the post English Farrow & Ball paint store; gentleman’s haberdasheries; and various ladies’ wear boutiques (“Your wife’s in here,” reads the sidewalk sign in front of one). It’s in these clothing stores that you can see embodiments of the old and new Oakville colliding. Chi-chi Tocca Finita carries glittering party frocks and designer gowns; the more old-school Barbette, established in 1958, stocks golfing skorts, power suits and tartan flannel nightgowns. If Tocca Finita sells trophy-wife glamour, Barbette retails beyond-reproach respectability.

In addition to its evident prosperity, the downtown reveals another surprising contrast to the surrounding suburbs. Between outpriced boutiques, there’s ample evidence of a cultural brook bubbling merrily, if not flooding. On the banks of the Sixteen Mile Creek, just north of the Oakville Club, there’s a sizable glass and concrete library and performing arts complex — home of a theatre complex and symphony (full disclosure: my Toronto-lawyer-by-day father played cello with them for years). Dotted about the business district are pottery and dance studios, decent art galleries and that disappearing breed of enterprise, independent booksellers and toy stores (more disclosure: my mother and business partners have run Pick of the Crop Toys and Books since 1979). Variety stores stock The New Yorker and Manchester Guardian. Over the years, the town has produced (or hosted) its fair share of talents: musician Hagood Hardy (composer of “The Homecoming”), actress Sarah Cornell (Ulla in The Producers) printmaker Naoko Matsubara, novelist Dennis Bock (The Ash Garden) and operatic tenor Michael Schade.

But the dominant impression is one of unabashed opulence; everywhere there’s dismaying evidence of jumbo salaries financing large living. Gone is the English circumspection about consumption: Oakville now gleefully participates in the American-led consumerist orgy.

All at once, the town assumes its least attractive guise. I recognize Oakville in pitiless reminiscences of similarly upper-crust towns in movies (Ordinary People, The Ice Storm) and in books (John Cheever’s angst-ridden short stores). It becomes the sort of place whose inhabitants expend so much energy keeping up appearances that they have little to waste on those who are near, but, in the end, not so dear to them. A place where people go to escape the city’s complexities, its many ethnic and financial disparities, to surround themselves with Other People Just Like Us. A place with the high schools you see in John Hughes’ teen flicks, filled with annoyingly cosseted students whose main worries are the prom, popularity and which all-expenses-paid university to choose. Oakville is such a place, but even in this foul temper, I know that this is but a partial picture.

A man’s reach must exceed his grasp, or what’s a heaven for? — Robert Browning

St. Jude’s was once the holy of holies for me. It’s where I first heard The Messiah, clapping inappropriately at its end. For many years, I sang in the choir under the chain-smoking organist, the late Mel Evans. He was hooked on the classic hymns and had trained under Healey Willan, the dean of Canada’s composers. Evans tended to play loud and, in our two practices a week, infected us with his love for the music. But the blush came off the Anglican rose for me when Jim Ferry was purged from the priesthood in the early ’90s for being gay, for practicing it, if not preaching it..

Not much has changed. During today’s services, I try to pin down the characteristic aspects of the entry-level theology traditionally bandied about here. If Jews and Catholics are stereotypically tormented by guilt, WASPs are trained early on to behave perfectly, to win academically, athletically and socially, and not to break a sweat while doing so. The high road is the only road. One of the prayers we intone (“That we may perfectly love thee and worthily magnify thy holy name”) underlines how central to this faith is the aspiration to excellence — and the intolerance we should have for anything but. We identify ourselves as unworthy, miserable sinners who will henceforth turn over a new leaf. This perhaps explains how Oakville at once attracts and alienates: its quest for perfection is both appealing and off-putting.

But there’s another, more liberating doctrine that’s been preached here intermittently over the years. In the church’s parish hall, with its stained-glass window depicting a diadem-wearing Queen Victoria, we once saw an animated film of an Oscar Wilde fairy tale. The tale, we were told afterwards, was a meditation on Christ’s alleged dictum, “In my Father’s house, there are many mansions.” I remember it, because it seemed nonsensical for mansions to exist within houses, but I knew even then what it meant: there was far more space up there than we down here think possible. Perhaps God or, in his absence, right-thinking humans judge each of us by how we’ve used our gifts, rather than on what score we tally in life’s little games.

With this memory, the town takes on a fresh hue. Instead of something from The Ice Storm, Oakville now resembles Bedford Falls, the eccentric-filled hamlet in It’s a Wonderful Life. It is a town made pleasant by generations of fundamentally decent people, upstanding voters, charity-donating churchgoers, brave veterans of world wars past, hard-working professionals who have sweated to give their children every advantage.

This is the puzzle of a place like Oakville: can any town so favoured by fortune be truly healthy? In the end, Oakville is neither a marvel nor a horror. It has many mansions, but it needs to find more space for the comedies and tragedies that periodically enliven and dampen everyday life.


In the piece, I was trying to speak about privilege and to distill the essence of Anglo. After years away from Oakville, I could see the town which seemed normal to my child’s eyes as odd, its customs quaint. In an increasingly multicultural North America, it looked almost exotic: the church teas; the white-clothing-only tennis matches; the croquet on lawns mown with manual rotary clippers — “well-played!”; these bookish WASP families, playing charades, putting on Shakespeare plays on the side-lawn. I thought of that French movie title, The Discreet Charm of the Bourgeoisie. A movie I’ve never made it through, but love the title.

Obviously, there’s a politics to all of this. The Have Nots are unlikely to see much charm (discreet or no) in the way the Haves conduct themselves. White wasn’t just the preferred colour for tennis togs.

In the piece, I came out as gay, one of the first times I did that in print. I’d come out in my life years prior, in 1988 — still, how unsafe that felt to put it down in black-and-white. Ho-hum, why bother? I found I couldn’t really write about how alienated I felt in my teens in Oakville, without speaking to that. How there seemed (at that time) no place for me in this pretty, pretty world. As is evident, I’m sure, from the piece, I was one of those teens who left for university, swearing they’d never come back.

What should have been said more clearly: how lucky I was to grow up without the financial pressures that ruin many childhoods; and how often in my life — and in this piece — I’ve shown insufficient gratitude for that great good fortune. For my parents’ hard work, for their care and the good examples they set.