Next up we're doing the Lanikai Pillbox Trail, along Ka'iwa Ridge in Kailua, a suburban beach town on the windward side of O'ahu. You're hiking from close to sea level up to a series of WWII pillboxes along the top of the ridge, so the initial part of this trail is fairly steep. But it's also a very short hike with amazing views, so it's usually packed with people; by some accounts the first couple of pillboxes are the most popular Instagram spot in all of Hawaii. I have no idea whether that's true, or how I'd go about finding out, but it seems at least believable. The trail continues on along the ridge top after the second pillbox, curving away from the ocean, and the crowds quickly thin out after that. I did the full length of the trail, which ends up at a second trailhead on Kamahele St., just outside the gate for one of those gated communities built around a golf course. I did meet a handful of people on this part of the trail, mostly going the other direction, like maybe they were taking the back way to the pillboxes. There was one group of Japanese teenagers that I remember quite clearly, not because of the serious hiking gear they had, or the very polite way they asked me to verify they were going the right way, but because one of them was lugging a boombox along, blaring dubstep of all things. Dubstep has never struck me as ideal hiking music, exactly, but whatever gets you up the hill, I guess.
I haven't seen anyone else remark on this, but there is one spot along the trail where you can (and I did) take a wrong turn. On the map above, see the little kink in the trail where it stops heading south and heads due west to the second trailhead? At that point a side ridge joins on to the main ridge, and it's big enough that an unwary hiker might think it's the main ridge and continue along what certainly looks like a ridgetop trail, albeit not as well maintained as the previous parts of the trail. I think I went a few hundred yards in that direction before checking GPS and noticing I was nowhere near the official trail, and was pointed directly away from it, and decided to backtrack. It was a nice and scenic bit of trail, I have to say; I just have no idea where it goes or how long it is, and the fact that it appears to head straight toward a nearby Air Force base was a real disincentive to go blundering around aimlessly in that direction. I've searched the interwebs since then to see if anybody has at least mentioned this deceptive little side trail, but I haven't come across anything like that so far. If anybody out there knows, feel free to leave a note in the comments below; I'd kind of like to know where I would have ended up if I hadn't had that gut feeling I was headed the wrong way.
Updated (12/15/19): Ok, I found a couple of old pages (as in, circa 1997) about the side trail I briefly wandered off onto. Seems the trail heads along the side ridge back toward the ocean, going over Pu'u o Lanikai and ending up at Wailea Point. So apparently it's fine, or at least it was 22 years ago, in the previous century, before 9/11 happened or Instagram existed. Those are the only references I've come across, so I'd still be interested in knowing whether anything's changed since then. Anyway, those two pages are linked from the author's old-school home page, which says it was last updated in April 2001. Surviving home pages from the early interwebs are a rare species these days, and I feel kind of nostalgic wandering around his site; I see at least one Gopher url so far, and one of his hike reports (dated 1995) mentions asking for advice on Usenet (!). I mean, some would argue that surviving personal blogs from the mid-2000s (like the one you're reading now) are also weird relics of a bygone age. I do kind of miss those days -- less surveillance, fewer walled gardens run by vast mega-corporate monoliths, fewer Nazis, almost no Russian or other state-sponsored trolls. I imagine today's net will also be a weird bygone era at some point, but I have no idea what's going to replace it (hence my ongoing non-billionaire-ness). I just hope it's not even worse.
