Ulupaina is four mile loop that starts near Kahekili Highway. The trailhead is located across from The Ko'olau Shopping Center in Temple Valley. Looking at the cemetary from The Ko'olau Shopping Center, the start of the trail is located on the lower left corner of the cemetary. High grass obscures the trail, but after a few feet of pushing through the grass, an obvious path begins to head uphill. The trail splits shortly after. Either direction can be done, but after doing the trail, I think the route we took (clockwise), is an easier option.
Justin, Kim, Kulani, Kelven, and I decided to try out the trail that hiking guru Dayle Turner calls "a lesser known trail." It may be, but the trail was pretty easy to follow and not overgrown at all. Plus, there's ribbons on branches that make the trail easy to follow.
The onset of trail contours around the bottom of a low ridge for about half an hour. It then begins to climb steeply to gain the crest of the ridge. After some short but steep ascents, the trail veers sharp right to follow the ridge line back to where the trail begins.
We didn't follow the sharp right junction just yet. Instead, we followed the ridge mauka to a powerline. According to Kulani's GPS, we topped out at 991 feet at the powerline, with a view overlooking Kaneohe to the southeast and Kahalu'u to Kualoa to the northwest. Behind us was the vertical cliffs of the Ko'olau mountain range. Further progress upridge looked possible, but a faint trail led the way. Beyond the faint trail was an impossible looking ridge that jutted straight into the clouds.
The route back along the ridge gave us a good workout. The ridge has a lot of ups and downs and some long, steep ascents if the trail was done in a counterclockwise direction. Aside from the steep hills, the ridge is wide and does not get dangerous at all; however, the trail does become hard to follow on some sections along the ridge. Good hiking judgment should be used when encountered with these sections, and following ribbons (which this trail lacks on the sections where the trail is faint) is a must.
Ulupaina took us a little under three hours to complete. It would have been faster to complete if we didn't take a long break at the powerline. The weather was also extremely humid; we started the trail right after a heavy rain. I'd definitely do the trail again, though. If anyone were to do this trail a few times a week, they'd be in top shape guaranteed.