Picking up just south of the Wilmette stop on the UP-N Metra line, the Green Bay Trail connects Wilmette to Highland Park, where you can ultimately pick up the Robert McClory Bike Path. It’s a short ride through Evanston from the North Shore Channel Trail, as such a pretty low stress ride to get to.
This trail definitely has its moments. It’s paved for about half of its total length, and dirt and gravel for the rest. While the trail is fairly well-maintained during the summer, it was pretty rough and rutted when I was on it in early spring. Much of the pavement could use reworking, too. There doesn’t seem to be a clear transition between dirt and pavement; some sections are randomly paved after a dirt stretch. It can also be difficult to figure out where exactly the trail picks up and leaves off in some sections. They would really do well with better signage. The trail itself doesn’t provide watering stations, but because it runs so close to the Metra, you can usually refill at a Metra station house.
More concerning, the trail is very narrow through a few parts, barely fitting two cyclists passing side by side. You’ll also want to remember that the trail passes directly through Ravinia and can truly be hell if there is a show going on.
The trail ultimately ends in Highland Park, near the Metra stop, and a Dairy Queen. From here it’s a few blocks through Highland Park on streets to where you can catch the Robert McClory Bike Path and continue north. Fortunately, this segment through Highland Park is well signed.