To plan your Strava picture or message, all you need is a street map, a pencil and a splash of imagination.

Since I launched into my Strava art obsession on January 1, the question people most often ask me (apart from “Are you insane?”) is some variation of “How do you do it?”

Do you create a route at strava.com and follow it on your Garmin? Do you have an app that maps out messages and pictures? Do you ride these routes “freehand”?

Though I’d love to say it’s the latter, it’s actually none of the above.

At its essence, my approach is decidedly old-school: grab a map and a pencil and start planning.

Because the route-sketching process involves a lot of trial and error (“How would it look if I took the path through the park instead of the main road?”), I prefer to work with digital paper and pencil. Erasing and retracing is far easier, and the end result is a PDF that I send to my iPhone and use as a map when riding the route.

Strava art planning, step by step

1. Far and away, the most important tool is a detailed street map. In Photoshop, I pieced together oodles of Google Maps screen captures, sufficiently zoomed in to show most of the street names. The resulting city map is my base layer.
2. For each new message or picture, I create a new layer and plan the route using Photoshop’s paintbrush. Where street connections aren’t clear or when going off-road would benefit the artwork, I zero right in with Google’s Earth view and street view to explore the possibilities…or I hop on my bike and do some reconnaissance.
3. As the image or message emerges, there’s lots of zooming in and out to test the effects of small changes to the route.
4. Once I’m happy with the result, I make the route layer semitransparent (so I can read the street names) and save it as a PDF – a map to follow en route.
5. As I find it easiest, during the actual ride, to follow written directions, I type out turn-by-turn directions from the starting point to the end. I keep a hardcopy tucked in the front of my jersey for reference as I ride (a couple hardcopies if it’s raining, as they get soggy and fall apart after a while).