It’s not exactly what you’re after, but this might be a place to start: https://trailrouter.com/
How it works: https://trailrouter.com/blog/how-trail-router-works/
You provide a start and end point and desired distance. It generates one-way or looped walking/running-oriented routes. I’m not the creator, I just use it occasionally.
Looks really cool with interesting options ! I love the "prefer green areas" option.
Re:Three Hundred Walks
by ChrisMarshallNY on Thursday September 30, 2021 @05:57AM
(#28704651)
Don’t know about automatic, but a friend of mine wrote an iOS route planning app that has proven quite popular: https://apps.apple.com/us/app/easyroute/id605127860
He's probably got the chops to do it, but no idea if he'd think it was worth it.
Is there an app that will generate walking routes, so you visit different streets each time?
If I wanted to develop something like this, where would I start?