Diamond Head

This is a great big loop around Honolulu’s most iconic landmark, Diamond Head. The route also leads up a hill which opens to sweeping views of the East side of Honolulu. Along this run, you’ll see high-end homes, beautiful city parks, surfers on the beaches below, and migrating humpback whales if you’re there at the right time of year. It’s hilly: 200 feet elevation gain in just under 4 miles.

Begin your run along Paki Ave and continue straight onto Diamond Head Road until you get to Fort Ruger Park. Take a left to continue on Diamond Head road and back down the hill to Kapiolani park. Look for the water fountains by the lookout, Fort Ruger Park, and by Kapiolani Community College. At the end of your run, you pass a number of eateries on Montserrat if you want to reward yourself with a coffee or snack. Another great add-on for this route is to time it with the Saturday market at Kapiolani Community College.

If you really want a work out, add in a visit to the Diamond Head State Monument ($1/person to walk in) and climb the 99 stairs to Diamond Head’s scenic overlooks. The hike takes about 40 to 60 minutes to reach the 760-foot summit of Diamond Head, a volcanic tuff cone. With all the visitors here, you will not be able to run to the top. No worries however, the steep incline will keep your heart rate up!

There’s paid parking in Kapiolani Park along Kalakaua Ave and free parking around Fort Ruger Park and some of the surrounding neighborhoods.