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Emily and I decided to take the dogs, Uila (WEE-la) and Koa (KO-a), up the Moalepe Trail up near us between the Wailua Homesteads and Kapahi. After passing by some pastures on a gradual ascent along a washed out dirt road, we got up into the foothills for some incredible views of Sleeping Giant, bits of the ocean and Kaua'i's central mountain, Waiale'ale (which was covered in clouds, as usual).
The trail is 2.5 miles and you may catch the quarter-mile markers beginning around 2 if you keep an eye out. There is a sign marking the end of the trail at a bridge with a cool grotto area. I strongly recommend continuing on the Kuilau Trail up around the grotto area to a breath-taking lookout about 100 yards beyond the sign.
A half mile further (so 3 miles out) is a picnic area with a near-360 view, open grassy area big enough for a football game or frisbee, and simple picnic pavilion. If you stay on the trail you will end up at the Keahua Arboretum, another possible starting point that is not as far (you would be taking the Kuilau Trail to the picnic area).
Getting There: This is an East Side hike up behind Kapa'a. Take Olohena Road all the way until it ends with Waipouli Road. You will see the dirt road clearly marked beyond the metal the gate.
What to Bring: Bring at least a quart of water, especially on a hot day. Sun protection is recommended as lots of the hike in the beginning is exposed. The trail is rated as moderate with gradual gains and descent; very few steep sections. A few muddy spots but overall not bad at all (for Kaua'i!). Trail can be slippery at points but most of the time it is wide enough for a vehicle. We saw cyclists and horseback riders in addition to hikers - dogs did fine and great one for them!