For several years now, I have toyed with the idea of doing a tour where every day brought a guaranteed all-day tailwind. Easy to do--you just start in a windy place at a windy time of year (Dodge City, Kansas in April, say) and start riding downwind, in whatever direction that happens to be. Do the same thing the next day, and the next, and the next.

Of course, this would probably involve a certain amount of zigging and zagging. But so what? It's not like you have to double back on precisely the same route if the wind switches 180 degrees from one day to the next. You could just diagonal a bit so as to see different country. Given two weeks or so, it would be interesting to see where you ended up--Nebraska, Iowa, Texas, Missouri--or maybe still in the middle of Kansas. I find the uncertainty of the whole thing kind of appealing. Admittedly, the beginning of tornado season on the plains could be a concern, but that doesn't necessarily seem like a deal breaker to me.

I don't suppose it would be a good idea to hoist a sail, but it might help to plan a bag and pannier system that gave the wind some surface area to push against.

Is this a stupid idea? Has anyone here ever tried anything like it?

I’ve thought of doing “I’ve Been Everywhere” in order. Your idea is certainly a different tack. I wonder what the average surface wind looks like as streamlines, if it more or less parallels the jet stream.

It's called RAIN. (ride across indiana)

I'd sat worth doing once in a lifetime, probably not twice.

Interesting idea.
If you don't want to just wing it, it seems like someone with good programming skill and access to a weather database would be able to model such a route quickly from recent historical data that includes mean wind vector.
Pick a start point, mean wind vector +/- a few degrees, and a distance range per day, then pick that day's endpoint city within your range.
Then repeat.

Sounds like fun if your comfortably self supported. Back in the day I had some fun days exploring with a couple coin tosses at every intersection. Wanting to see what happens next is a personality trait I've seen in active folks who make it into their 90's. If you needed to have a more definite , but still naturally defined itinerary, trying to follow a watershed from headwater to ocean might be fun.

Never having toured, and living in a place where cycle tourists always ride north to south, this sounds like fun! You do have to be prepared with enough water and food, as the states you're talking about have very long distances between towns; you also need to be ready to stealth camp for the same reason. And make sure to have a phone with a good weather app, as tornado season is not something to take lightly.

Just ride, and see where the wind takes you. Yep, sounds great. Please keep us posted on your plans.

But it doesn't always go with the wind, does it? Or does it? I ask in genuine ignorance.

I love your idea. I don’t like riding in wind and it’s always windy here except in the morning. I don’t like being constantly moved around but I especially hate the howling in my ears and it’s not smart to ride with ear plugs.

In the plains states the wind runs 20-40 mph. Amazing tailwind, "unpleasant" headwind.

Point taken. I have done quite a bit of touring (and non-touring) and bored through a lot of headwinds. Agreed, it is part of the experience. But I just thought it might be fun to try a ride with no set plan or destination, and no headwinds. Just for the sheer hell of it.

There's also this Frank Zappa song:

Neat idea. Couple it with routes that are always downhill, and I think you'll end up in the center of the earth.

Not 100% guaranteed, but more than likely.

jonwvara if you are not familiar with this website which depicts the winds of the world, check it out. It defaults to surface winds, but can show winds at altitude as well as air pollution, temperature, air moisture, etc., and the Northern Lights. Oh, and ocean currents if you ever take up sea cycling! I tried to center it on Cabot, VT.

Earth Atmosphere

And here is what it looks like.