I had a fun little route where I used to work.
Started out quite flat then had a climb which was long, flat then a steep downhill. At the bottom of the hill turn around and back up - the challenge to see just how far up the hill I could make it. then just retrace the route back.
It was actually a lolipop route.
It's quite good if there are hills as you won't be running the same route twice, the challenges are quite different. My two hills started (finished) at the same point but one was short and steep, the other long and not quite so steep.
Learn how to use a map and compass properly.
Get a decent navigation book out of the library or buy one, or look out for a course. Go out and really practice with a map and compass when walking and take your time with it. Learn to read contours, take bearings etc. If you know someone who can navigate well, go with them and get them to teach you.
You need never struggle again. A map and compass will not crash/run out of batteries/lose signal. You'll be able to plan a route with a decent idea of what it will be like, and follow it without getting lost. When out, frequent checks are the key to staying on route.
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