One such wanderer is Ned Merrill, the peculiar protagonist of The Swimmer, the short story by John Cheever that inspired the cult 1968 film of the same name with Burt Lancaster in the titular role. The vigorous Ned (“Neddy” to his Waspy cohort) makes a cartographic discovery one brilliant, sunny afternoon. A series of swimming pools, mostly privately owned, perhaps a dozen or so, are located such that he could “swim” his way back to his home. He dubs this route the River Lucinda, after the wife he imagines to be waiting for him at his journey’s end. Adrift in more ways than one, Ned’s aquatic map is more than a shortcut; it’s a way for him to recontextualize his environment, to give it a new reading.

Tall, tanned, and muscular, Ned represents a fantasy of masculinity, a certain era’s portrait of the American Dream. Another pillar of manliness was our famously fit 26th president, Theodore Roosevelt (“Teddy” to his cohort.) An original Rough Rider, Roosevelt was always ready to throw down. One of the favorites of his eccentric exercise regimen was to open a map and randomly select a destination to hike to from the White House, walking a straight line to his destination regardless of whatever happened to be in the way. Over, under, or though, but never around, any obstruction or body of water.

Roosevelt’s workouts were a forerunner of what we now call parkour, the training discipline that uses the found objects of the urban environment as an obstacle course. Parkour opens up new perspectives on everyday surroundings. One begins to see the city through “parkour eyes,” which invert aesthetics. Places that have not previously been seen as attractive or appealing start to reveal interesting details and opportunities for inventive moves. Those guys checking out the clinker bricks on that old warehouse? They’re probably more interested in a clandestine climb than in Dutch building traditions.

Practitioners of parkour are called “traceurs”: they are “tracing” (drawing) a unique and ephemeral path through the city. In effect, a traceur is a hard-core flâneur, that urban stroller who wandered the streets not to work or shop but to study those who did, effectively turning the city into a laboratory. The flâneur was originally a literary construct in 19th-century France, and it was in the writings of the poet Charles Baudelaire that the flâneur became forever linked to the streets and shopping arcades of Paris. Baudelaire was an idler, a consummate dandy, an urban drifter—the exact opposite of a traceur; it is impossible to imagine him doing a monkey vault over a Jersey barrier. Yet when he posits, as he did in The Flowers of Evil, that “the true voyagers are only those who leave just to be leaving; hearts light, like balloons,” there is a clear shared desire for a new kind of adventure. The flâneur and the traceur are attracted to the labyrinthine streets and hidden spaces of the city, participating in but remaining somehow detached from it.

Urban playfulness and “drifting” are characteristics of “psychogeography,” defined by Guy Debord in the 1955 Situationist International as “a whole toy box full of playful, inventive strategies for exploring cities . . . just about anything that takes pedestrians off their predictable paths and jolts them into a new awareness of the urban landscape.” For Debord and others like him, the metropolis was a stable, contained, and solid place of prescribed circulation. It is only when we allow ourselves to “drift” through an environment, ignorant of established boundaries, that we truly make new discoveries. This act of drifting was called a “dérive,” a walk that resisted the tyranny of the modern city.

Some of Debord’s more imaginative heirs are the Hash House Harriers, an international network of running social clubs. Most major cities have a chapter, with members generally meeting once a week to run a unique course (a “hash”) through the city, the route of which is known only by the “hare,” the individual tasked with premarking the course with flour or chalk. The chaotic nature of these runs, the false trails, shortcuts, dead ends, and such, force the faster runners to slow down to find the trail, allowing stragglers to catch up and ensuring that physically disparate runners work together as a group to navigate their surroundings. Beer is involved. (The Hash House Harriers are self-proclaimed “drinkers with a running problem.”) Equally revered and reviled, the Harriers are forever rewriting the city, “Etch-A-Sketching” new routes weekly, only to shake them up and start over the next.

Delightful detours abound in the world of social fitness networks, where services such as Strava and Runtastic use GPS data to allow runners and cyclists to chart and share their own courses. As one might expect, there is little overlap between the posted routes and the recognized bike paths and jogging trails in a given city. Runners are a competitive, independent breed. Check out the subculture of Strava Art, where participants use their movements to trace gigantic symbols and texts, ranging from the juvenile and profane (too many phalluses to count) to the genuinely transcendent such as Michelangelo’s David on the streets of Victoria, British Columbia. (Fans of the IFC series Portlandia will recall the episode in which the mayor insisted the Portland Marathon follow a course defined by a rather intricate rose symbol, and the hilarity that naturally ensued.) Specialized apps such as GPS-A-Sketch (“The Earth is a giant sketching toy”) facilitate and encourage these efforts. Similarly, the apps Dérive, Drift, and Serendipitor send users on random trips through their own cities, helping them get “lost” in familiar places and share their experiences and findings to a broader community.

Ned Merrill’s pool-hopping odyssey is a source of derision for his lethargic and superficial neighbors: “Now why would anybody do such a thing?!” was a typical scoffed response. Ned has a crackpot idea, to be sure, but it is born of a yearning for adventure that only beautiful weather and an obsession with physical fitness can bring. And although his epic trip ends in tragedy (as most epics do), each step of the journey peels back yet another layer of the story, revealing secrets about Ned and his privileged milieu. A lost soul perhaps, but to be lost is to go against the grain, to open up alternative or “resistant” readings of a given text, object, or environment. Ned’s life may be illusory, but his geographic project is not. If only we could all move with such imagination, play, and provocation.