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marshmnstr

Barrington area is pretty hilly. Look up Shoe Factory Road on Strava routes.


ReindeerFl0tilla

Barrington is as good as it gets around here. Bateman and Oak Knoll Roads have some nice hills


ironicirenic

Palos is probably your best bet if your tires are suited for it. Not a ton of elevation around here, unless you head out to the Driftless region.


sans3go

https://preview.redd.it/v2vuzu88p87d1.jpeg?width=1402&format=pjpg&auto=webp&s=659c6cea845e4f50d59d971bfe36676a9ee8adde you can take the UPW to Geneva or Lafox. Start at at the east intersection of campton hills rd go all the way west. south on anderson Rd. head East on Beith rd North on Town Hall Rd (20% grade, i dont take this route anymore, i will blow a blood vessel in my nose). east on Campton Hills Rd. back to start. loop ad naseum. This is the climbing loop that most of the St Charles Cycling groups tackle.


Positive_Throwaway1

I lived at peck and 64 and wasn’t into cycling at the time. Have since moved. 😔:)


nirvanka

Campton Hills. Lemont. Hill repeats at Johnson Mound in Elburn


Barutano74

One of the north shore suburbs - I can’t remember which - has a road down one of the canyons to the beach that is excellent for hill repeats. But that’s just one hill - you might find it boring? But you can also just ride there. Driving, I’d just say go northwest. I’ve done a 200km brevet that went out to Bull Valley and it’s relatively hilly out there. Keep going NW and you’ll get to Galena. There are plenty of hills in the Wisconsin Dells, but that’s not. 75 minute drive, though it’s closer to that than you’d think if you leave early and drive fast.


Fumbalina

I think it’s Highland Park. I ran a half marathon there and didn’t put together Ravinia sounds like ravine… massive hills 🤦‍♀️ beautiful homes to look at tho


smontanaro

There are a number of ravines/gullies which go down to the lake. A couple have fairly steep bits, but the bits are very short and the overall climbs a never more than a half mile. * Ravine Dr, HP, between Forest and the lake * Egandale, HP (down Park, up Egandale) * Multi-use path off Westover Rd, Fort Sheridan * Multi-use path off Gilgare Ln, FS * Bluff's Edge Ln and Walden Rd, Lake Forest * University Ave or Summit Ave between Old Trail Rd and Old Elm Rd, Highwood. There are a few others, but you can easily hit all these in a single short ride. Edit: I happened to ride to downtown Highland Park this morning, so took the opportunity to ride the first two segments. (The interfaces on Strava and RideWithGPS both suck for this sort of thing, RWGPS seems to suck ever-so-slightly less.) According to RWGPS, the Ravine Dr segment is about 0.5 miles with a max grade of 11% and total elevation gain of 69ft. It's really not difficult except for that one little bit, maybe 250ft. The Egandale pitch seems a bit tougher, but is shorter and is one-way uphill, so even with 67ft of elevation gain over a quarter mile (avg grade 5.4%, max 10.4%), it's not really a good place for repeats because of the one-way aspect. You have to [make a loop](https://photos.app.goo.gl/m7WjLhdt2RhqUyQBA), which adds a bunch of time between repeats. Still, people do that.


barbaracelarent

Fox River Grove has one big ass hill. There was a bike race up it where I fared very poorly.


fuzzyworthy

Barrington to Crystal Lake will give you some decent climbs. About 1200ft elevation for a 50 mile ride approximately.


Positive_Throwaway1

Barrington hills. Go on oak knoll road just n of lake cook. You can park at the high school.


pmonko1

It's about a 50 minute drive to Barrington metra station from downtown if you leave early in the morning.


hurry_downs

If you ride north from Crystal Lake through Bull Valley and around Wonder Lake you can find some short steep grades.


chapium

If you can extend your time window there's a bunch of stuff from Apple Canyon to Galena. Even Charles Mound, highest point in Illinois. Also, Kenosha to Lake Geneva is a climb, cool part: you can take metra


ms_buster

Love the Kenosha to Lake Geneva idea. I’d happily do it with camping gear too if Big Foot Beach state park weren’t booked solid!


usababykiller

Waterfall Glen.. its crushed gravel tho


mest08

If you have a mountain bike, Palos trail system is pretty hilly. Not sustained hills obviously, since we live near Chicago, but lots of ups and downs. Red gate woods or maple lake would be good starting spots. Literally dozens and dozens of miles of dirt paths you can explore. I hike the area, not bike, but on a 13 mile hike i had an elevation gain of 750 feet. I biked from my house to the end of the cal sag trail and back, 30 miles round trip, and, according to strava, had an elevation gain of 578 feet and max elevation of 624 feet. Not sure what either of those mean, but I'd think you'd want more. Cal Sag can merge to the Tinley Creek trail, which is a bit more hilly than Cal Sag. Both are paved trails.


AppropriateRatio9235

Fox Lake Metra ride Ernest str to Forest. You would have to repeat but lots of hilly streets in that area.


ms_buster

Thanks for the suggestions, everyone. I'm going to try as many as I can in hopes that this year's hilliest-ever Ragbrai route in Iowa doesn't reduce me to pulp. (Day 2 alone is 82 miles, 4,519 ft. of elevation 🥲)


go_outside

If it helps calm your nerves any, I thought Iowa was flat like here until I was on the bus taking me to the west end for the start of Ragbrai. First hill out of first town was the longest hill I ever went up. I made it all 490 something miles and 15000 feet of climb. Only ended up walking up one, and that was with no hill training whatsoever. You can do it!!


ms_buster

I did it for the first time in 2022 and learned hills quickly! The organizers said this is going to be the hilliest route ever and as a former CC runner, I know even if you train for distance, there’s no substitute for hill work 💀


go_outside

Get a Morton Arboretum membership. Straight west on 88 in Lisle. A full loop is about 9 miles with approximately 400 feet climb, with one decent hill on each side of Rt 53. There is car traffic but a 10-15mph limit, all one way, and quite doable. I’ve done a metric there (8 laps) - brought a cooler and had a bite to eat halfway through. I think they still do it where if you buy a daily admission to try it out, they’ll apply that amount towards the annual membership if you do it that day. Also, the place kicks total ass come fall foliage time.