Trail Running in Hawaii

After discovering trail running, settling for a treadmill may become impossible.


Barbara McAllaster, Laura Kloepper and Bob McAllaster take on the Pillbox trail run.

Photos: Mark Kato

Trail running forces you to break free from a metronomic pace, challenging you with varied terrain and forcing you to pay attention to your environment. But it rewards you, too. While jogging may lead you down a sidewalk, hyperventilating in car exhaust along Kalanianaole Highway, the trail takes you to places where the trade winds pump unsullied air across your path. This weekend, why not take your running to another level, and hit the trail?

Aiea Loop Trail

The Aiea Loop has it all: roots to hop over, bends to dance around, a semi-spongy ground surface—at least, compared to concrete—that provides forgiving padding for joints, strawberry guava in case you need to refuel and eucalyptus-scented air to fill your lungs. Shade from the forest canopy helps keep you cool and the loop makes sure you do not get lost. There’s also a gentle, rolling elevation change that is mild compared to more challenging trails. It’s a pleasant introduction to trail running. Tip: Start the trail from the upper parking lot.

Kaiwa Ridge/Lanikai Pillbox (Extended)

Past the pillboxes, the trail traverses the ridgeline that forms the backdrop of Lanikai. You’ll run along with a splendid view of mansions, palm trees, reef and outriggers. When you reach the descent at the end of the ridge, turn around for an “out-and-back.” Catch a sunrise on this trail for the ultimate experience. Tip: No trail-running points will be deducted if you decide to walk the approach.

Kealia Trail–Mokulaia

Did someone say switchback? Well, they should, because there are plenty on this trail. Kealia starts with a steady ascent through dry forest. Exposed terrain soon takes over and the trail becomes an open field of visual activity. Gliders soar overhead and the North Shore unfolds below. This is what trail running is all about: a challenging, vertical rise to 1,600 feet plus in roughly three miles, and rich scenery. Continue all the way to Peacock Flats and get a rare view of Mākua Valley. Tip: Get an early start to avoid the unforgiving sun.



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Honolulu Magazine April 2018
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