I need suggestions for hilly areas within a 1-2 hr drive or (preferably) train ride of Chicago.  I'm training for Dairyland Dare and short of driving 3 hrs up to Dodgeville before the August 10 race, I'd like to practice my shifting on hills closer to Chicago.  

Major bonus if I can get there by train with my bike. I've ridden in Three Oaks/Indiana Dunes area but it doesn't loo like the South Shore line allows bikes, which is really disheartening.  I need to be able to do it as a day trip.  

I know that anything this close to Chicago isn't going to be nearly as hilly as the areas west of Madison, but something is better than nothing. 

Your advice is much appreciated! 

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I know people that go ride Egandale Road in Highland Park (make a loop with Linden and Park) dozens of times in an attempt at getting elevation change. Seems kinda pointless to me.

You could do interval training instead, it would help. Chasing the few hills we have around here is going to be an incredibly inefficient way of spending whatever time you have allotted for training. Even just riding your bike for that 4 hour round trip that you've made time for would probably help as much, if not more, than doing "hill" repeats for a couple hours.

There is a member of the Chainlink who tells the story of training for hills by loading up her bike and riding up and down bridge overpasses.  Boring, but effective training.

Southwest side (Palos area) plenty of rollers and such. Search routes on Map My Ride and segments on Strava. In addition, check out Waterfall Glen. It's crushed limestone but it's packed fairly well and would be fine on a road bike. It has a near one mile grade that avg's about 1.5% with steeper pitches in some segments. I'd explore there before driving hours away.

In addition, plenty of parking garages in the loop that you could hit as well. Kinda hamster wheel, but you're going up.

Which distance of the Dare are you doing?

I have a great 2-part route totaling about 55 hilly miles that starts and ends in Lake Geneva.

Originally based on routes from a book by Lon Haldeman I believe.

Could post it here as an attachment if interested.

Thanks everyone! Those are helpful hints - keep them coming!  I might consider hamstering a parking garage for the novelty, but I doubt I could do it more than once without fear of getting hit by a car (especially coming down). 

Peter - we were thinking of the 150k, but the bailout contingency plan is the 100k, which is becoming increasingly likely as the date gets closer.  Nonetheless, we're in this for the experience, not to beat a number, so either is fine.  

h' - that would be great if you post the attachment when you get a chance. 

There is a garage at Van Buren and Franklin. 13 stories and open air. The risk of getting hit by a car is minimal as the up and down ramps are one directional. It's just short of a half mile going up with a consistent grade and would be a good place to test your shifting. It's an automated garage so no personnel to hassle you. Weekend mornings are usually not too busy there.

Good luck at the Dare. Sounds like a fun ride.

Putting some weight on your bike and doing intervals will do just fine, even if it's not necessarily as interesting as riding actual hills. I managed to become much, much better at hills without even knowing it (until I rode some mountains out west for the first time in years) just by doing my normal riding in Flatland.

Evanston Bike Club has done hill training rides using the beach access roads on the north shore. They are short but are quite steep.  There are good hills at Lloyd and Tower in Winnetka. There is another near Park in Glencoe and another in Highland Park.  We have long used these roads to train for the Hilliy Hundred in Bloomington, Indiana, I know that on the ride schedule Hank Scheff will be leading some of these rides soon as the Hilly is in October. Check www.evanstonbikeclub.org  Here is a cue sheet for a 40 mile hilly ride that uses some of those hills. http://documents.clubexpress.com/documents.ashx?key=0%2bBwL%2fUf%2f...

You can come out to Princeton on Amtrak.  I've mapped 23 hills in the arean that MapMyRide classifies as Cat 5s.  Most are close enough together that you could ride them all in one day.  Free guide service is available.  I'll even loan you a bike if I have one that suits you.

Please share!

h' 1.0 said:

I have a great 2-part route totaling about 55 hilly miles that starts and ends in Lake Geneva.

Originally based on routes from a book by Lon Haldeman I believe.

Could post it here as an attachment if interested.

From the first post:  I'd like to practice my shifting on hills closer to Chicago.  


I live in Highland Park and, yes, that beach access road is pretty steep.  About 70-80 yards but you climb .. what, 40-50 ft?  So it's  in that 10-20% grade range.

What you'll figure out is which gear is best for climbing THAT particular grade, seated or standing.  It's a good little workout, too (if you repeat), but I think your training needs are probably better met locally.


If you want to practice doing a variety of grades on a much more interesting route, I'd recommend a trip to Lake Geneva.  I do their annual Fat Tire Memorial Ride which is a charity event that loops around the lake and hits a half dozen bars along the way (yes, it's a pub crawl).  It's a 20-mile loop and provides a variety of climbs, some of which are pretty tough and long but doable if you're in decent bike shape and you'll get used to shifting on climbs.  The first thing to learn is to start in an easy gear--the opposite doesn't work so well.


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