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Re:Three Hundred Walks by troydavis on Thursday September 30, 2021 @07:14AM (#28705053)
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.

Re:Three Hundred Walks by pjerem on Thursday September 30, 2021 @10:11AM (#28706525)
Looks really cool with interesting options ! I love the "prefer green areas" option.