At roughly 11:00 in the morning, I, along with thirty others, ducked out of an alley into one of Corktown’s serpentine laneways. A woman in a nightgown, standing in her doorway, gawked at the congregation, surprised. A crooked, uncomfortable smile on her face, she waved her open palm at a man with a camera. “No pictures!” she yelled. “No pictures!”

I was inspecting a stranger’s window box when I heard the commotion, and, looking up, irritably scratched my eyebrow.

It was my first time participating in a Jane’s Walk, an annual weekend of volunteer-led free tours held in cities around the world. Named for the revered urban theorist Jane Jacobs, Jane’s Walks are only in their fourth year. For being so new, they are a startling success; in 2010, a total of 424 walks were offered in 68 cities across 9 countries. Jane’s Walks are unusual for city tours. Instead of showing off the icons, Jane’s Walks offer tours of only common spaces — alleys, laneways, graffiti, public parks, and the like. The walks are an invitation to explore the city’s pedestrian arteries, a chance to contemplate urban space and awe at its beauty.

Jane Jacobs’ breakthrough work The Death and Life of Great American Cities, first published in 1961, is often cited as the most important book on urban planning ever written. It is a vitriolic critique on the idols of the modern city and a love song to the eccentricities and idiosyncrasies of urban life. Despite public reverence for her work, she often complained that not even her benefactors put her work into action. “Nice words from politicians, planners and columnists hardly matter when we continually repeat mistakes we made decades ago,” she once said to Stephen Wickens at the Globe and Mail. “It’s like we made some progress, then hit a wall.”

The year following her passing, her friends and admirers inaugurated Jane’s Walk as a way of sustaining the discourse she fostered in life. The concept is free local tours led by neighbourhood volunteers. Want to lead a walk? Build a walking route around the spaces in which you live, and explain how and why you have come to love them.

I took a number of tours. The turnout was surprisingly large. I was never in a group with fewer than 30 people. The crowds were usually older (between 30 and 50 years in age) and they were typically dressed for comfort: weathered running shoes, spring jackets, Lululemon stretch pants. Many brought dogs, and some, young children. No one foresaw the weather — by mid-afternoon, everyone was sunburned and dappled with sweat.

We thrilled at the chance to explore the hidden places: the alleys behind Bright Street where neighbours convene and host block parties, or a small Danforth neighbourhood that is only accessible by traversing green space on foot during certain nighttime hours. The hosts were invariably thrilled. They talked excitedly to the crowds, often about the trends in community history or the recent spills in local politics.

The rhetoric of a Jane’s Walk is always the rhetoric of community action — street lamps, drainage, neighbourhood watches, city councillors — and tends to be rather sterile. One gentleman made extensive mention of the community developments spearheaded by a neighbour who was seated on a balcony fifty yards away. He spoke about the new ice rink, looked up, and waved.

But on Jane’s Walks, words of any shape feel inadequate when describing the experience of the city up close. Vision takes on the quality of poetry more than anything, what Wallace Stevens termed “description without place.” The streets, scrutinized, transcend themselves; peculiar aspects of architecture become communicative; the jagged angles of the alleyways emote. The odd slopes and curvatures of laneways are trodden first by the imagination, then by the body. An air of mysticism begins to invade the mind, and soon even the familiar appears magical. Never have I so thoroughly enjoyed a streetcar, nor have I contemplated so deeply the walking island by Christie Pits Park.

In the fashion of Jacobs’ ideology, Jane’s Walks are intended to use walking as a way for communities to coalesce, to combat the isolation of city living. The use of walking in an urban environment as a tool for transformation, however, is not without precedent.

Guy Debord, situationist thinker and founder of psychogeography, elucidated the concept of the dérive, an unplanned tour through the geography of an urban space, directed only by the various attractions of one’s surroundings. The word translates in English simply as drift. It is, according to Debord, a chance for an utterly new, authentic experience. To the situationists, the dérive was a method through which the drifter could come to better understand his or her own psychological responses to the encroaching and, more importantly, spectacular surroundings.

Similarly, Charles Baudelaire identified the flâneur, a person who walks through a city in order to experience it for its aesthetic dimensions. To Baudelaire, the flâneur was an objective observer — an onlooker who was present but ultimately detached from the city, and therefore able to see it most completely.

But while walking, I confronted a problem over which both Baudelaire and Debord agonized: staring, as we were, into the windows of Corktown houses and Annex mansions, the locals might have rightfully figured us to be voyeurs. On some level, everyone in a densely populated city sector has to eschew their own privacy — a person fashions their house, like their clothes, in the way they would like to be seen by others, and after all, Jacobs argued proximity to one another is the one hope for true urban community. There is no sense in feeling bashful about attending a Jane’s Walk and eyeballing people’s houses, but it is easy for an urban observer to forget that, unlike a painting, the city gazes back.

Later, a young man biked past our group as we stood in front of the Tranzac. “So many white people,” he yelled.

“My God,” I said aloud, “he’s right.”