How to make long walks easier
A Long Walk Is Mostly a Logistics Problem
The difference between a pleasant 8-mile walk and a miserable one is usually not motivation. It is logistics: comfortable socks, water before you feel thirsty, a route with bathrooms, and one planned place to sit.
I also check the weather for heat and air quality, not just rain. That matters in New York, where a sunny route beside traffic can feel very different from a shaded park path.
Walking is often presented as a character test. My read is that it works better as basic systems planning. Make the healthy choice easier to continue.