The 606 (Bloomingdale Trail)

The 606 runs 2.7 miles along the old Bloomingdale rail line, between Ashland on the east and Ridgeway on the west. Because it is elevated and has no cross traffic, it is one of the few genuinely uninterrupted long walks on this side of the city.

There are twelve access points, roughly every quarter mile, and seventeen ramps for step-free access. Several parks sit along or beside the trail, including Walsh Park and Churchill Field — both of which have their own Dog Friendly Areas, so you can combine a walk with off-leash time.

Dogs are welcome but must be on a short leash. The Park District says so explicitly. The trail is narrow and shared with cyclists and runners, so a long lead is a genuine hazard here rather than a matter of etiquette.