Start at Walsh Park, the eastern terminus of The 606, named with a nod to Chicago's universal zip code prefix. You'll set off along the elevated trail built on this former railway line.

Pass Churchill Field Park, a green space bordering the trail's route through the neighbourhood. You'll get a breather among trees and open space before continuing west along the tracks.

Walk alongside North Milwaukee Avenue, once home to a toll road torched by an angry mob in 1881. You'll trace this historic corridor that has anchored Bucktown's commercial life for generations.

Wander through Bucktown, a neighbourhood whose boundaries mysteriously kept expanding through the 1950s and 70s. You'll uncover how factories, immigrants, and shifting real estate reshaped this scrappy patch of Chicago's north side.

Continue into Wicker Park, the neighboring district known for its artistic revival. You'll hear how artists were deliberately recruited here to breathe new life into a struggling area.

Reach North Western Avenue, the longest continuous city street in the world at 24.5 miles. You'll stand at this sprawling corridor as the trail continues west into Logan Square and Humboldt Park.

Pass Margie's Candies, a beloved neighbourhood sweet shop with old-school charm. You'll catch a glimpse of this local institution, a favourite stop for generations of Chicagoans.

Spot Club Lucky, a classic Italian-American supper club steeped in old Chicago atmosphere. You'll take in a slice of the neighbourhood's mid-century character, still thriving today.

Finish near Lottie's Pub, a longstanding neighbourhood watering hole. You'll get a feel for the local nightlife that has kept Bucktown's community spirit alive for decades.