The 606 / Bloomingdale Trail
An elevated rail line turned 2.7-mile greenway — flat, car-free, fully stroller-accessible.
Why you'll go
A stroller-easy roam above the city through Wicker Park, Bucktown, Humboldt Park, and Logan Square. Wide open path to practice walking, sky and treetops, people-and-dog watching.
What they'll love
At the two ground-level park entrances, little ones get the trail's best toys: Walsh Park at the east end (1722 N Ashland) has a playground with a sandbox and a push-button ground-jet water-spray feature, while Julia de Burgos Park at the west end has a giant spider-web net climber paired with a big spider art installation and a low sitting wall. In between, the paved, 14-foot-wide path is a wide-open runway for a new walker to toddle car-free, elevated about 17 feet above the street.
Real talk
12 ADA ramps about every quarter-mile; a 10-ft path. No restrooms on the trail — plan a stop at an adjacent park. Shared with cyclists; keep right.
Don't miss
- Walsh Park spray feature + sandbox (east end) The eastern-most ground-level access point at 1722 N Ashland is the toddler jackpot: a playground with a sandbox plus a spray feature where small jets shoot up from the ground after you press a button. The water comes right up out of the play surface, so a curious toddler can wander into the jets. Pack a swim diaper and a towel on warm days, and start your visit here rather than the trail — it's the easiest entry with the most for under-4s. There's also an athletic field and basketball hoops on site.
- Julia de Burgos Park spider web + spider sculpture (west end) At the Logan Square end, this access-point park has a spider-web net climbing element plus a giant spider that doubles as art and a climbing structure, alongside a long sitting wall with nature-themed art — concrete, named features a toddler can point at and climb the lowest rungs of. It's a smaller playground, so it pairs well with a short trail walk rather than being a full destination on its own.
- Roll the flat, ramped trail between the parks The 2.74-mile path is paved, sits elevated above traffic, and has 12 ADA-compliant access ramps spaced roughly every quarter mile, so you're never far from a stroller-friendly way up or down — a genuinely car-free place to let a new walker practice. Refill the sippy cup at the drinking fountains: up on the trail at the Western, Rockwell, and California access points, plus at street level at each entrance and in Julia de Burgos Park.
- Plan a bathroom + snack stop Public restrooms are behind the McCormick YMCA (Ridgeway) and at the Trailhead building (Western). Family-friendly food sits right at the exits: Ipsento coffee at the Milwaukee Avenue exit and Bang Bang Pie & Biscuits at the California exit. There's no restroom on the trail deck itself, so change a diaper before you head up — the ramps are gentle but it's a hike back down to a bathroom mid-trail.