About this experience
The Bloomingdale Trail was built on a former railway line that once served as the industrial backbone of Chicago's north side. On this self-guided audio tour through Bucktown and Wicker Park, you'll hear how the factories, immigrants, and artists who lined these tracks transformed two scrappy neighbourhoods 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. 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 neighbourhood. 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.
At a glance
- Duration: 30 min–1 hr
- Private experience
What is included
- Lifetime access to this tour in English before your booking date and after it
- Offline access to audio, maps, and geodata
- Flexibility to explore at your own pace with a self-guided GPS tour
- App for Android and iOS
- Directions to the starting point so that when you’re in the right place, the tour will start
Not included
- Smartphone and headphones
- Personal expenses for admission fees not included during the tour
- Food and drink
- Transportation
Itinerary and highlights
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.
Meeting and pickup information
- This tour starts at Walsh Park Trailhead. Before arrival, please install the mobile app and use the code provided on your confirmation ticket. Detailed starting point instructions are available after downloading.
Languages and tickets
- English — Audio
- English — Written
- Mobile Only
Tour operator
- VoiceMap Audio Tours
Meeting points and locations
Accessibility and practical details
- Wheelchair accessible
- Infants and small children can ride in a pram or stroller
- Service animals allowed
- Public transportation options are available nearby
- Transportation options are wheelchair accessible
- All areas and surfaces are wheelchair accessible
- Suitable for all physical fitness levels
Cancellation policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
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