Bucktown and Wicker Park: A 606 Bloomingdale Trail Walking Tour

The Bloomingdale Trail was built on a former railway line that once served as the industrial backbone of Chicago's north side. On this walking tour through Bucktown and Wicker Park, you'll hear how the factories, immigrants, and artists who lined these tracks transformed two scrappy neighborhoods into some of the city's most sought-after real estate.

The tour starts at Walsh Park, the eastern terminus of The 606, named with a nod to Chicago's universal zip code prefix. As you head west along the elevated trail, you'll pass the converted factory buildings of the Felt & Tarrant Manufacturing Company, whose mechanical adding machines helped America win both World Wars, and look across to Saint Mary of the Angels Catholic Church, a St. Peter's Basilica lookalike that served as a lifeline for Polish immigrants arriving in the early 1900s. You'll also learn why Bucktown's boundaries kept mysteriously expanding through the 1950s and 70s.

Further along, you'll stop at the Damen Avenue Arts Plaza, where the Flat Iron Arts Building stands as a reminder of how artists were deliberately recruited to revive a struggling neighborhood. The tour ends at Western Avenue, the longest continuous city street in the world at 24.5 miles, where the trail continues west into Logan Square and Humboldt Park.

On this 30-minute tour, you'll have a chance to:

• Hear the story of the 1929 Saint Valentine's Day Massacre getaway car, discovered burning in a nearby garage
• Learn how the birthplace of Slam Poetry sits on Honoré Street
• Discover how the Churchill Cabinet Company went from crank telephones to Pac-Man machines
• Find out how Milwaukee Avenue's toll road was torched by an angry mob in 1881
• Spot the Stenson Brewing Company site, where a mobster fought Prohibition all the way to the Supreme Court

Lace up your walking shoes and let a long-time neighborhood resident show you what most trail users walk right past every day.