To be in transit is to navigate a void between points of departure and arrival. When we’re in an airplane, untethered to the earth, time and space roll by indifferently. Only seldom does a vague sense of location present itself through the oval window—green irrigation circles printed on the Plains, dotted lines of city light woven in the darkness, black granite peaks locked in ice.

On road trips, these captivating pauses come at shorter intervals between the on- and off-ramps, at gas stations, diners and cheap motels. Jack Kerouac’s unspooling tale,On the Road, follows his vision of “one great red line across America,” but gathers its tone and value in the dingy waysides of the route. It begins inauspiciously, with rain coming down hard at Bear Mountain Bridge on Route 6. Wait...