John Seymour's excellent I-cannot-recommend-strongly-enough book "The Forgotten Crafts" actually has some great ideas here I think - both for Taurinor specifically, and all of us generally who want a better picture of life in the Shire and Breelands both. It's written by a near-contemporary of the Professor, also a deep lover of the English countryside, and is full of wonderful illustrations of that life:I'm still deciding on an occupation - tailor fits my skill set best, but I'm hoping I can find something in the text to support something a little more outdoorsy/trekking-friendly.
John Seymour's The Forgotten Arts and Crafts[/url]
(Sold as "The Forgotten Arts," "The Forgotten Crafts" and "The Forgotten Arts and Crafts" - as far as I can tell they're all the same book, just released at different times under different titles)
What immediately came to mind that Taurinor might be interested in was the trade of bodger. It's not trekking per-se, but nonetheless a trade that would get Ned out in the woods for a season at a time. Bodgers would go out into the woods with tools, set up camp and simple lathes, and just turn out chairs and such all season long:
Other "done in the wildlands" crafts mentioned were coppicing, hurdle making (wattle fencing), rake and hayfork making,broom making, handle/haft making, ladder making, (corn) crib making, peg making, clog cutting, charcoal burning, and basketmaking.
I could easily imagine in the forests around the Breelands a bodger camp would have a couple of their younger, stouter lads patrol for trollsign now and again - where they'd surely occasionally come into contact with Rangers.
Anyhow, just a thought. And again, a strong recommendation for the book, especially as it can be found used on Amazon for a song.