I live in Chicago, but never get enough training in (especially with hills) unless I travel back to Iowa for some weekends. Are there any good areas to do some long rides around Chicago? Obviously, I know about LSD and some of the local bike paths, but they’re often too crowded and not long enough and do not have any hills.
You can take I-90 out to the Fox River Trail. Park at Trout Park which the trail runs through, and you can ride the paved trail north to Ringwood, about a 50 mile round trip. If you ride a hybrid or mountain bike, you can continue farther on a gravel trail to Wisconsin.
Some very nasty hills on the north side of Crystal Lake in what is called Veterans Acres. Suggest you do them slowly the first time until you learn the turns.
You can also ride the Fox Trail south of Trout Park, but it goes through a few more towns, and is more heavily traveled.
You might also try the Wheeling Wheelmen, they used to run a lot of rides out in that area, lots of fun hills around Bull Valley and McHenry
If your looking for routes with hills, scenic country roads and don’t mind a drive, come join some feloww RAGBRAIers in Ottawa, IL. I’m with the Starved Rock Cycling Assoc. and you are welcome to join us. Our club rides don’t start until Spring, but I have been riding most of the Winter when above 25 degrees.
I would also recommend a great 2- day ride in June that has plenty of great hills and is an awesome prep for RAGBRAI. TOMRV is run by the Quad Cities Bike Club.
This will be my fourthe RAGBRAI, and I have done TOMRV every year and once I get to Iowa in July I have no trouble with the hills!
This isn’t a trail per se, but team xXx has a Saturday training run open to the general public. Details are in the link below. It’s a great team to ride with. You’ll be pounding it, and everyone’s drafting. I had fun and was stretched to my max last year. Am training this winter to be able to ride with them come Spring.