Worthington Glacier in Alaska. Photo by Troy Moustache.

Living in the moment is always the best way to tackle life, right? Pick a destination at random, hop on your bike, and just go. Ride hard for a few days in the general direction you think you should be heading, and then when you’re in the middle of nowhere with low supplies and lower water, you can use that sense of reckless abandon to keep yourself going. Yeah man. Living!

If the above sounded good to you, why are you even reading this? Go lube your chain and get the hell out of here. For everyone else, let’s talk about route planning and map making.

Getting from Point A to Point B on tour is never as simple as that. Instead, Point B becomes Point X, and a whole lot of other points get added in between. This is half the reason touring is so much fun. Most of the time you’re going someplace you’ve never heard of and would otherwise have no reason to stop there, and when you get there, it exceeds your nonexistent expectations. Ever heard of 1880 Town? No? The home to the largest collection of Dances with Wolves memorabilia? Don’t even get me started.

Luckily, in today’s modern world, there are a lot of resources available for finding your way. You could buy a map at a gas station. You could photocopy pages of an atlas from the library. You could do an internet search for “maps.” You could even use a third party resource to sell you a sweet mapped out route (available in PDF, hard copy, and GPS coordinates) that includes stops and ride details (elevations, equipment recommendations, badger warnings, etc.). For this last method, you should check out Adventure Cycling’s website. They have over 40,000 miles mapped throughout the U.S. of A., guide thousands each year, and take a lot of stress out of planning if it’s your first tour.

Since we are not made of money, we’re going to forego the last method and just use free electronic resources. I’m going to use Google Maps and its sister site, Google.com. We’ll take a look at a week long tour from Chicago to Minneapolis, but the steps can be applied to any tour.

Step 1) Using mapping software, find the route from your Start to Finish.

We’re going to start in Chicago and ride out to Minneapolis. According to Google Maps, the most direct route by car is 409 miles. We’ll assume (correctly) that riding a bicycle will be less direct, as we won’t be on a highway the whole time.

Chicago to Minneapolis by Car.

Step 2) Switch to Bicycle Mode on your map.

Switching from car to bicycle changes the route to 452 miles. This isn’t a final number, but a pretty good guess as to how far you’ll be riding. You will likely have multiple route options, so choose the one that interests you most. I will be going north then west through Wisconsin.

Chicago to Minneapolis by Bike.

Step 3) Set your daily mileage goal with a +/- range.

You need to have a mileage range to use as a limiter each day. What’s the furthest you’re willing to ride, and what’s the shortest? I set a goal of 90 miles per day with a +/- of about 20 miles. I don’t feel good riding less than 70 (unless it’s on beastly hills) and I try to not stretch too far past 110 if I don’t have to. It’s good to note that you usually ride further than your goal, so if you set your goal at a century, be ready for 120+ days. Your goal will be based on a lot of things: physical fitness, desire to stop and site see, hatred for waking up early, and more. I hate waking up early, but have no problem riding well into the night, so my 90 is mostly a limit based on physicality.

Step 4) Find an endpoint for Day 1.

There is probably an easier way to do this, but the new Google Maps is still somewhat foreign to me. Make a clone of your current Google Map tab, and zoom into an area on your route that looks to be as many miles from your start as is your daily goal.

Now, in that area, search for the type of place you’re looking to stay. For some, this could mean “state park,” “camping,” “campground,” etc. For others, it could be “motel,” “hotel,” or “fantasy resort.” Once you have a list of potential matches, do some research. Is the campground open? Does it allow tent camping? If you’re in certain states that start and end with the same letter, you’ll find that “campground” means “RV camping”, not “tent camping.” Mindblowing.

As for hotels, I wouldn’t recommend booking ahead of time unless you really need to guarantee your room (if you’re riding to Sturgis during rally week, for example). Typically the cheapest hotels aren’t listed on Google, and you can book them when you arrive. It’s just good to know you’ll have a fallback option if there isn’t anything cheap when you get there.

Regardless of where you stay, do some research now to save yourself trouble later. If you pick out a sweet spot to stay (state parks are usually pretty wonderful, in that they have full amenities, great upkeep, better views, and are dirt cheap), you’ll have something to look forward to if you have a bad day of riding. Even if you’re going to guerilla camp, you can at least use a satellite map to find a place with good tree cover to hide in.

Back to the example: In my search I was able to find the Pinewoods Campground near Ottawa Lake Recreational Area. At 116 miles, it’s a little beyond the far end of my daily goal’s range, but I know I can push myself, plus with all this summer sunlight, what’s the harm in riding a little late?

Step 5) Map the route to Endpoint 1, and save it.

Redo Step 2, except from your Start to Endpoint 1. Then save your map with a name that will help keep your days in order, like “Day 1 – Chicago to Pinewoods Campgrounds (116)”. Once saved, it’ll be quickly available from your smartphone during the ride.

Step 6) Repeat Steps 4 and 5 until you reach your final destination.

Update your map to go from Endpoint 1 to the End. Look for spots to stop in your daily goal range. Map out that new route. Save the map. Repeat this process until you have every day saved as a map.

You’re going to have to adjust your days according to what’s available on the other days. You may be forced to stop after 60 miles because the next stop isn’t for another 90. You may also extend your route depending on the different campground availabilities. It’s very possible that you’ll pick spots for Stop 1 and Stop 2, and then realize there’s no good place for Stop 3, so you have to start all over again. It can be an iterative process.

Luckily, Wisconsin and Minnesota are littered with state parks, recreational areas, and other types of campgrounds, so I had a lot of choices for each day. My map list looks like this:

  • Day 1 – Chicago > Pinewoods Campground (116)
  • Day 2 – Pinewoods > Mirror Lake State Park (108)
  • Day 3 – Mirror Lake > La Crosse, WI (94)
  • Day 4 – La Crosse > Frontenac State Park (88)
  • Day 5 – Frontenac > Minneapolis, MN (76)

Chicago to Minneapolis by Bike with Daily Segments.

I was able to get three state parks in there plus one night in a cheap hotel. This is a very direct route, though. If I wanted to see larger swaths of Wisconsin, I could add an extra day or two on here no problem and probably camp the whole time. That would all be a function of this step.

That’s it. You are now ready to ride a bicycle from Chicago to Minneapolis in five days. Seems like something you could handle, doesn’t it? Using this sort of methodology, you can cross a state or country in manageable chunks.

Two final notes. The first is that some organizations that sell route information will provide a free PDF overview of their routes on their website. It just shows the route’s general shape, not the exact roads. This can be used as an overlay for creating your own maps, which can be handy for avoiding sketchy roads. Secondly, you can bypass exact route creation if you have a smartphone/GPS. Just pick a series of end points for each day, and then each morning plot your day’s ride. This is my preferred method.

Remember that everything is a matter of perspective. You can intimidate yourself out of an amazing experience if you look at a tour in terms of total mileage rather than miles per day. A 1,000 mile tour is just twenty 50 miles days, right? You’re already applying this sort of relative thinking to other parts of your life, just apply it to touring too. Think about it this way… You go to work every day because you only think about it in eight hour segments. If I told you that you were going to spend over 1800 hours in an office this year, would you ever get out of bed?