[robertbalent]

That’s a lot of walks!

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?

[troydavis]

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.

[pjerem]

Looks really cool with interesting options ! I love the "prefer green areas" option.

[ChrisMarshallNY]

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.