This word has a lot of associations and collocations and senses – but even more if you live in Alberta, because many major roads in those cities (especially in Calgary) are called trails (as Wikipedia says, “A particularly unusual use of the term is in the province of Alberta, Canada, which has multi-lane freeways called ‘trails’”). In Calgary, main roads include Crowchild Trail, Sarcee Trail, MacLeod Trail, Deerfoot Trail, Barlow Trail, Stoney Trail, and the one that makes British people laugh, Shaganappi Trail (“shag a nappie? haw”)… When I grew up, it was as though there were two words trail, one being a thing you hiked on, and the other being a major road (or in a few cases ordinary streets that were once more important: Edmonton Trail, Banff Trail). Trail is often used for skiing, too, but I grew up calling downhill ski slopes runs – they were never narrow enough to qualify as trails.
For most of my readers, naturally, that second sense is not part of the usage set of this word. But trail has a whole bunch of other collocations and senses. We might as well follow the trail from the beginning, or at least from as far back as we can see in English. And that is a verb meaning “drag behind” – as in trailing and trailer and trail along. The oldest English noun senses are in reference to things that drag behind, such as what we now call trains on dresses; from that came a sense of the mark left by something dragged behind, or more generally the path or, um, trail of evidence left by something that has passed by: hot on the trail. And from that we get a worn path… and for those of us who live in or near mountains, a trail is not something you leave behind you but something you walk on to go somewhere you have not been (obviously someone else was there first, of course, and left the trail for you to follow).
And so we get an interesting web, not trail, of interconnected meanings. If you look at Visual Thesaurus, trail has eight nodes it connects to; four of them interconnect, and another two join together to lead to “train”. The original “lag behind” sense is one node; “move draggingly or slowly” is another. But the ones that form a web are three noun senses – “evidence pointing to a possible solution”, “a path or track roughly blazed through wild or hilly country”, and “a track or mark left by something that has passed” – plus a verb sense, “go after with the intent to catch”. There are more than a dozen various synonyms, but the one that is a nexus for these four nodes is track.
And what words does trail show up with? Go to Word and Phrase .Info to find out: campaign trail, paper trail, mountain trail, trail blazer, trail map, blood trail, nature trail, follow the trail, leave the trail, hike the trail, hit the trail, trailing wind, cross-country trail, groomed trail, marked trail, scenic trail, historic trail, rough trail… and of course there are terms such as trail boss, trail bike, trail head, trail-riding, trail mix, and such trail names as Trail of Tears, Appalachian Trail, Lillooet Cattle Trail, Dalton Trail, Oregon Trail, Bruce Trail, Chilkoot Trail… and a few towns named Trail, notably one in British Columbia. (There’s another in B.C. called Field. And yet British Columbia is full of much less plain place names such as Illecillewaet, Okanagan, Koocanusa, the Bugaboos, Spuzzum, and (of course) Vancouver.)
So naturally trail has tastes of all this; it also has echoes of betrayal, tail, rail, and perhaps even chill and jail. The word in its written form doesn’t have much iconicity of its referent. It doesn’t by itself present anagram opportunities. It’s a five-letter, four-phoneme, one-syllable word, yet three of its four phonemes are allophones that are not the usual sound of that phoneme: the /t/ is affricated before /r/ and sounds like “ch”; the /r/ is devoiced because of the preceding syllable-initial /t/; and the /l/ is the version we use at the end of a syllable, with the back of the tongue raised high and the tip possibly not even touching. And even the vowel may have an added slide to a schwa (neutral vowel) at the end, moving into the /l/.
Well, trails do go from somewhere to somewhere else, after all. And this word has left an interesting trail of just that.