Bike ride from Chicago to Wisconsin

Bike Ride from Chicago to Wisconsin… and Back!

When you read that, maybe you’re saying, “Hey, that seems like a long ride!” Well, you would be correct, and I would say, “Yes, 113 miles to be exact.” If it hurts your knees, ankles, or possibly even your butt just thinking about it, well just imagine how I feel. At this point, pretty good, but it’s also been two days.

This was the longest one day ride I’ve ever been on and my second century ride. My first century ride was earlier this summer before my RAGBRAI trip. This century ride to Wisconsin I did with my friend and fellow cycling enthusiast, Allison Wagner (There you go Allison, I gave you a name in this post instead of just “friend” like my last post). Allison was brave to join me and trust that I actually knew where I was going… when I obviously didn’t. I mapped it on Google Maps and had a few print-outs with me… Oh, and my trusty GPS (my phone). Either way, we were ready for an adventure.

The Original Plan: Chicago to Milwaukee

A big thank you to Amtrak for ruining our original plan. We really wanted to ride from Chicago up to Milwaukee, get something to eat, and then take Amtrak back to Chicago in the afternoon. Allison actually called Amtrak and found out that you can take a bicycle on the train, but it’s not as easy as just walking on the train with your bike. There are some things you need to do:

  • Get to the train station 1 hour before the train departs
  • Pay an extra $15 for a bicycle box to store your bike
  • Bring tools so that you can remove the pedals from your bike

With only a couple days to plan this out, there was no way were were going to do this. Plus, it would have cost us about $50 each just to get back to Chicago. We will bike from Chicago to Milwaukee at some point (possibly this October), but we’ll skip Amtrak and see if it’s cheaper to rent a car and do this trip.

The Mapped Bike Route and the Actual Bike Route

I had been looking at Google Maps for almost three weeks and finally a few days before our trip I planned a route that I wanted to take. The original bike route took us north on our usual route through the Cook County Forest Preserve via the North Branch Trail and then all the way north to the Wisconsin border via the Robert McClory Bike Path. It then headed west for a few miles along the state border and then picked up the Des Plaines River Trail and headed south for 30+ miles through more parks and forest preserve. It was a large loop that totaled 117 miles and brought us back to a point close to where we started. The great thing was that there was very little overlap, so we wouldn’t be bored with riding the same trail on the way back home.

Well, things didn’t quite work out that perfectly, but the route we ended up taking was still pretty interesting (The mapped route is not exactly accurate because we had a couple detours… explained later). We had quite a bit of overlap on our route, but it was actually nice because we knew exactly where we were going on our way back and where we could stop for lunch as well. Our route changed because the Des Plaines River Trail was crushed gravel (which we knew), but it was a lot harder to ride on with our road bikes than we thought it would be. After about 4 miles of riding on the trail we decided we would take the first decent looking road that headed back east to the trail we were on before.

At the next crossover street we stopped and took a look at the map. An older gentleman pulled up next to us and just as we had decided to cross the street and continue on the trail until we found a better street headed east, the older gentleman got on the road and headed east. I said, “Forget it, follow him!” Unfortunately, he was only on that road for about 1/4 of a mile and then pulled into a parking area where I’m assuming his car was parked. There was no point in turning around, so we continued on that road. It wasn’t the best road to be biking on, but it had some decent shoulders at times that gave us plenty of room to bike. The only obstacle we hit on this route was that the bicycle trail we were trying to get back on was not accessible from the road we were on… the trail had a bridge that went up and over the road. We had to get off our bikes and walk up this little side hill and around a fence just to get back on the trail. We were headed south and back towards Chicago in no time though.

A Biking Adventure

I’ve already told you about how our bike route changed leading up to the trip and also during the trip, but here’s a summary of our biking adventure.

We actually started at 6am, which meant that I was up at 4:45 that morning, packing and getting my bike ready for the trip. It was actually a perfect morning for biking… nice and cool with hardly any wind at all. We took our normal route north towards the North Branch Trail through the streets of Chicago with bike lanes. I don’t think we had ever been on the North Branch Trail so early before, and even though it was pretty empty, there were quite a few deer just standing next to the path… I think we counted 10.

The interesting part of the trip was once we got beyond the familiar part of the route. We got off track a couple times, but easily found our way back to the trail. We would usually realize we were off track when the road would start to get a little busier with traffic and the speed limit would go up… time to check the map! You could actually take the bike trail the entire way, but the trail was bumpy at times, so we would switch over to low traffic roads or streets if we could. Plus, the last ten miles of the trail into Wisconsin were so boring. It was just a straight trail with really nothing but trees on both sides. When we got to Wisconsin, we didn’t even realize it at first. We crossed a little bridge, a small sign (that did NOT say welcome to Wisconsin) and the trail became paved. You can see in the picture above that the sign on the trail just said “Kenosha County Bicycle Trail.” It wasn’t until we headed west along the state border that we saw the “Welcome to Wisconsin” sign that I snapped a picture of from a distance.

By the time we went west and then all the way back east after realizing the Des Plaines River Trail was too hard to ride on, I was getting hungry. I thought Lake Forest would be a great place to get something to eat because there’s a nice little main street with shops and stuff. Of course, that was still a good 15 miles south from where we were. Let’s just say we went through some interesting neighborhoods that we had sort of missed on our route north. We were riding a well known and traveled bike back, but I still felt like people were looking at us like we were from another planet. Anyway, to wrap up this summary, we made it to Lake Forest, got some sandwiches at Einstein Bros and were on our way shortly after Allison made fun of me for laying in the middle of the sidewalk to do some stretches. Ok, to be fair, I did look a little ridiculous.

We made it back to Chicago a little after 3pm which added up to a little over 9 hours of total trip time and 8 hours of actual biking time. Not too bad for 113 miles! Next time we do a similar trip, we’ll have a better idea of where we’re going. Next time to Milwaukee!

The Three Bike Trails from this Route

North Branch Trail – You can’t beat this trail, and I say that mainly because it’s paved and it’s a nice scenic ride through the parks and forest preserve. If I were to list the cons of this trail, I would say 1) there are quite a few cross streets, and 2) it gets pretty packed on a nice day in the afternoon.
Robert McClory Bike Path – This bike path starts just north of Ravinia and links up with the Green Bay Trail (which you can pick up at Ravinia, and also heads south towards Chicago). The Robert McClory Bike Path has a few different surfaces along the 30 mile route. It starts as sidewalk, switches to a paved path and ends with quite a few miles of crushed limestone path. The crushed limestone is actually a decent surface for riding on, because the limestone packs down pretty well so it can be flat and not as loose as crushed gravel. It would be nice if it was paved, but I can live with the crushed limestone. This path goes through some “interesting” neighborhoods… some nice, and some not as nice. The last 15 miles of the path are pretty boring, as there’s not much to look at and it’s just a straight shot until you hit Wisconsin. Oh, and once you reach Wisconsin the path is nicely paved… that’s the Kenosha County Bicycle Trail.
Des Plaines River Trail – Great scenery, but not really the best trail for road bikes. The trail surface is crushed gravel which makes it hard to ride on with thin tires. Seems like it would be a great trail for walking, running, or riding your hybrid/mountain bike on.

2 thoughts on “Bike Ride from Chicago to Wisconsin… and Back!”

  1. Tried to ride up close to Wisconsin today and took Sheridan until around Ravinia where we found the Robert McClory and took that as far as we could until we lost it at the Naval Base. Tried to reconnect with the trail but couldn’t find it again. On the way back rain pummeled down, but it was extremely enjoyable.

    Hope to do another long ride soon, just need a better idea of the mapping. Today’s ride was sort of “let’s see how far north we can get” and it worked out fairly well.

    Thanks for the informative post

    1. I was looking at the maps and trying to see where you lost the trail exactly. I believe that was right around the same area that we lost the trail a couple times as well. We ended up continuing on Sheridan, but that turns into a multi-lane road with quite a bit of traffic.

      I think I know where you lost the trail though and maybe this will help! When you get up by the naval base, the Robert McClory bike path runs along the left side of Sheridan (basically a sidewalk). You’ll get to this point where Sheridan is elevated and there is a turn-around that loops underneath Sheridan and 137 (that runs along side Sheridan). The bike path is supposed to do that as well, but I don’t believe it’s marked well (or at all). Either way, if you can get from there over to Commonwealth Ave, the bike path runs north from there.

      We figured this out on our way back to Chicago! I hope that this helps and next time you can follow this trail all the way up to Wisconsin. The trail isn’t overly smooth from this point north, but it’s better than crushed gravel. It’s paved once you hit Wisconsin… Good luck!

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