Green Bay Trail

I enjoy biking the Green Bay Trail. I usually take it from Wilmette up to Highland Park. It’s not the smoothest ride, and it’s confusing where you’re supposed to go at points, but it’s a fun, fast trail nonetheless. I especially like all the old stonework on the side of the path.

Updating to say that I’ve really come to enjoy this path for a nice relaxed spring/​fall ride.
Scenery gets much better past Glencoe but the roads are also more rough, so I don’t know how well road tires would fare on those trails, but it’s really gorgeous! There are also some nice segments from Kenilworth-​Glencoe (a park, some nice patches for grass for picnic, etc).
Yes, the lack of lighting still sucks, and having to get past the Wilmette portion for a peaceful trail is still pretty annoying (though after about the 3^rd time I finally remembered where to go at some confusing points), but I think the narrowness isn’t an issue given the relatively low volume of (much more friendly) riders and runners.
As much as I disliked the qualities of this path when I first rode on it, after so many trips it’s really grown on me, I guess. Plus, they just repaved may portions of the trail in the fall. There are still a lot of bumps for some reason, but it’s certainly quite a bit smoother.
Can’t wait for all the snow to melt!

I find the Green Bay Trail to be way more pleasant for riding my bike than the trail along Chicago’s lakefront. Even during the height of the summer, the trail is never overly crowded. The people I pass along the trail are usually friendly. The trail is quite peaceful and the greenery is beautiful. There are a few difficult crossings over streets, other than that, the trail is fine. I would only recommend riding during the daylight hours as there is practically no lighting along the trail, and traditional bike lights aren’t enough to light the way.

We love biking on the Green Bay trail. Often we travel up to lake forest for lunch we our kids.

I would definitely say it’s more on the 3.5-star mark but I round it up just for the sake of existing, and allow bikers and runners to have a place to perform their activities in relative safety.
No cars, at least. The Metra runs alongside you, so you won’t feel totally lost in the woods.
I rode it to the Chicago Botanic Gardens, and thought it was in pretty decent condition despite not being cared for. The trail is well indicated in Evanston and Wilmette, and I didn’t get lost once. Use common sense, have a look online before going out and you should be pretty much good to go.
Not the most scenic route, but big bonus points for taking you straight to the Gardens without meandering for miles like the North Branch Trail (which I loved, and is so pretty, but you shouldn’t be in a hurry to go from point A to Z).
Major drawback: lack of water fountains. I counted two on the portion of the trail I used… definitely not enough for hot summer days.
A good alternative route though.

a better map I think.
It seems to me there have been reports of crime on this trail after dark in the Highland Park area but I can’t provide specifics.

A local friend had told me about this trail a few years ago and I’ve been back numerous times ever since. It’s a great hidden gem of the north shore with miles and miles and miles of pleasant trails with changing nature across the seasons. I highly recommend a visit. It likely won’t be your last.

The Green Bay Trail actually goes all the way from Wilmette to Lake Bluff, running parallel to the Metra tracks. It’s a combination of paved/​gravel and even where it’s paved there is usually gravel next to it, a feature very welcome to someone who spends lots of time running there.
It’s never that crowded, even on weekends. However during the winter the trail is left to its own devices, pretty much rendering it unusable from late November to mid-​March.