Cough, cough, what I have always wanted to know: is it permissible to embark on a pilgrimage and ride a bicycle?
Absolutely! Personally, I originally intended to walk it but had some obligations that gave me a time restriction (I don't recommend that, it was very stressful in the beginning!), so I opted to do it on bike. This method had its own ups and downs, both figuratively and literally, but made provisioning and planning much easier in retrospect.
One of the key lessons I learned on my pilgrimage is not to judge yourself or others based on the means through which they "walk" the path. While it was traditionally walked, I met several cycling ohenro (two of whom became good friends), people walking it backwards, people on motorcycles, people in cars, and people on tour buses. Some were trying to do the whole circuit in one shot, others were doing it in pieces, others were doing it for the Nth time, and some were doing the pilgrimage as part of a larger journey through all of Japan (日本一周, another life goal).
Obviously, not every path that is walked is accessible by vehicle, and not everyone is physically capable of the same kind of journey, so every pilgrimage is different, and there's nothing wrong with that whatsoever. When I later encountered the
37 practices of the Bodhisattva (written in Tibet around 400-500 years after Kobo Daishi first walked around Shikoku), #32 stood out to me:
If, influenced by disturbing emotions, one points out another bodhisattva's faults, oneself is diminished. Therefore, not speaking about the faults of those who have entered the Great Vehicle is the bodhisattvas' practice.
This particular practice is referring to those who have taken refuge in the tradition of the mahayana (great vehicle), but in an expansive sense, all sentient beings are working out their particular karma on the same path that leads to enlightenment; some are just closer than others, relatively.
When I was in Shikoku, it was easy to get down on myself for taking an "easier route" by riding, compared to the walking ohenro I met, but this is just as wrong to do as to judge the elderly pilgrims visiting the temples by car or bus. When I visited Tibet for an arranged pilgrimage of sorts, I encountered pilgrims who were doing incredibly long and arduous pilgrimages on foot or even crawling, some doing full body prostrations with every step. We passed several of these from the luxury of our land cruisers, occasionally stopping to donate some money to support them. Some of these journeys take years to complete. It's all a matter of karma; we choose the pilgrimage we feel suits us, and then we all are at the mercy of circumstance to provide us with our experience. The only thing in our control is how we choose to react to it all.
If you're walking, your walking staff is symbolic of Kobo Daishi, as a reminder that he is treading the path with you. On a deeper level, you realize that as you progress on the path, you are not journeying alone, but that everyone you encounter is a part of that pilgrimage. On a deeper level still, you are not separate from any sentient being. And while you are having this karmic experience unique to you, any concept of separation from others is itself an illusion.
Long story short, ride on!