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Permalink Reply by MagMileMarauder on August 14, 2012 at 1:23pm

If you want to access to country roads fast, hop on the Metra and then do your 40-60 mile loop at the terminal end (the terminal ends are coincidentally located 40 to 60 miles from Chicago). The countryside will appear rapidly if you choose this way of riding. In Hyde Park,  there's a stop for the Metra Electric line which goes south to University Park. From there you can take different roads south to different small towns with charming Main Streets and a larger town like Kankakee.

There are many other choices of course if you pick another Metra Line.

Were you living in Madison before? You can take the UP-NW line that goes to Harvard(IL) and that's about 70 miles from Madison or 100 miles if you take the non-hilly graded rails-to-trails.

Want to go to Milwaukee? Hop on the Metra to Kenosha, and it's a 40 mile ride each way.

Here's the Metra system map.

Click on the route, and the website will give you the schedule for that particular route in pdf format.

There are some blackout dates for bikes, so keep an eye out for that. On weekends, unlimited rides are $7, which is friggin' awesome. I'd take advantage of it.

Of course there are some local trails that are closer to Hyde Park. The lakefront is an obvious one, which is 18 miles. Then if you go to Google Maps (bike routes) you'll see plenty of trails that are usually in the various Forest Preserves. There's also the Major Taylor trail in the south side, which is pretty nice. As far as sketchiness goes, you'll get a feeling about that soon, and hopefully common sense will prevail. Englewood and Woodlawn are two areas that come to mind, but even in those areas, there's a very high chance you won't be harassed.

Enjoy the city!

Edit: If you take the Metra with your bike, you'll need a bungee chord to secure your bikes to the seats. Some conductors will be strict about enforcing that rule. The bike cars are the ones that have the handicap logo, a conductor should help you locate one if you don't see it the first few times you decide to ride.

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Permalink Reply by S on August 14, 2012 at 1:47pm

There's a few nice routes that go south into Indiana and back.  You can get some hills depending on the routing but most of it's pretty flat.  If you are willing to bike north there's a few routes into the burbs north of the city with hills but most of the routes to go there end up taking the lakefront path or through the city.  Things change a bit if you're willing to take the Metra or drive out to the suburbs.

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Permalink Reply by Daniel on August 20, 2012 at 5:34pm

Thanks so much for the ideas!

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