Find the top rated cross country skiing trails in Chesterton, whether you're looking for an easy short cross country skiing trail or a long cross country skiing trail, you'll find what you're looking for. Click on a cross country skiing trail below to find trail descriptions, trail maps, photos, and reviews.
_143224_st.jpg)
_111257_st.jpg)
_161393_st.jpg)
Parts of the trail toward the west very nice pretty east of Hobart very bumpy and dangerous
Probably the smoothest bike asphalt ride that I have been on in the greater Chicago land area. Disregard all previous (dated) commentary on the conditions of the trail. It is smooth riding all the way from Joliet to Chicago Heights with just a few bumps once you are east of Metteson.
Love walking this trail. Quiet and safe mostly.
My 3 star review is because there needs to be signage when bikes pass, a shout out should be told to the walkers. Frequently I'll be walking and the bikes are so quiet it startles my dog or the bikes just squeeze by. It should be mandatory shout out “on your left!” when passing. Secondly, electric bikes are using the trail more often. Going 25-30 mph is not ok!
Same thing where most do not shout out when passing. Needs to be a rule regarding electric bikes.
We rode the GAP from Cedar Creek Park to the Boston trailhead at the base of the Historic Boston Bridge and back. About 36 miles round trip. What a great ride. Smooth trail with lots of benches and several picnic areas and toilet facilities. Well maintained. Passed through several little communities along the trail. No major highways and very few little roads to cross making it very safe. Got a delicious huge “medium” size ice cream cone at the “Big Twist” in Blythedale, right off the trail. Highly recommend this ride!
We rode the full length from the Chicago Botanic Garden to the end at Foster Ave. and back. About 40 miles round trip.
Nice paved trail with plenty of washrooms along the way. Saw 8 deer at various points, two just standing on the side of the trail as we passed and never moved at all.
There is a $12 fee to park at the Botanic Garden, which was no big deal to us. There are plenty of free parking areas at the many forest preserves along the trail. Botanic Garden is great also, if you have the time to go through it.
The trail makes a loop around the Skokie Lagoons, but I would recommend only doing the east side. It has way better scenery and is quiet. Not so on the west side.
I took a star off for the following:
1. There are a lot of big road crossings. Golf road, Dempster, Touhy, and a really nasty diagonal one at Devon & Caldwell. All the walk buttons worked fine and you need to be patient, but they are wide and rather intimidating. The diagonal bridge over Oakton and US-14 is quite impressive though.
2. This is a greenway, so lots and lots of blind curves. This would not normally be an issue, but the road bikers are going too fast around them and there are a lot of pedestrians.
3. Other people have commented about the rude road bikers and we did encounter a couple of them. Most are courteous and tell you when they are coming by, but we had three at road crossings that pushed their way through and cut people off like they were going to a fire.
Over all, a nice trail and a great getaway for people living in the suburbs, but you've got to pay attention so it's not as nice as many sleepy rail-trails.
We kept the scooter the scooters under 25mph . Perfect tail for walking/ e bikes / scooters . Everything was clean and in good shape when the wife and I visited. Busy trail . Make sure u have a bell on ur motorized anything for the blind corners . Keep the speed down . Highly recommended.
It is July 2026, and the 294 closure on the trail is not open to use. Please update in the review section.
Drove down from South Bend. Started at CR700 and rode to North Judson and back. Class 2 e-bikes. Nice, quiet trail. Maybe saw 10 people total. Decent shape for the most part. A few rough spots and low hanging vegetation. Plenty of shade. Didn’t venture into town this trip. Will definitely be back.
I have been riding this trail for three years now. (2024 - 2026) No more. The gravel has, in many places, turned dusty, deep and slippery. You might enjoy the gravel on a gravel bike. I ride a skinny tire road bike. OK for the first two years. Not OK this year.
Ride day: Sunday July 12, 2026 We started at the Panhandle Trail Head at Country Road 50 N. Only real downed was the parking at the trail head. Only 3 spaces available and 2 were taken. Was a touch tricky, but we got it. We rode North through the town of Royal Center and on wards. After an hour give or take we turned to head back. The trail is perfect. Fairly straight trail with all kinds of wildlife and beautiful scenery all around. Only a few minor root bumps on the trail - but they were all marked. Even some rest rooms along the way! Will ride again without question - great trail.
TrailLink is a free service provided by Rails-to-Trails Conservancy (a non-profit) and we need your support!
Scan the QR code to get TrailLink on your phone
Map Search
_177065_st.jpg)
