Best Short and WFH-friendly Hikes on Oahu

Oahu made a fantastic WFH location for me the week after Thanksgiving 2022. I had visited the Island before, so I didn’t feel the need to take vacation time to sightsee. What I did, however, was take some time either before or after work to check out some of the shorter hikes on the island. This was not exactly an easy task as a lot of hikes on Oahu are short in distance but have significant elevation gain and/or treacherous sections on ridges. Here are my 6 picks for short hikes on Oahu plus one popular one you should skip.

Diamond Head – 1.9 miles, 515 ft EG

Diamond Head is probably the best known hike on Oahu. The crater is part of the system of cones, vents, and their associated eruption flows from the Koʻolau Volcano. These eruptive events created many of Oʻahu’s well-known landmarks such as Hanauma Bay and Koko Head, the next hike on this list. Hiking up the tallest side of the crater is just under a mile one way with 500 ft of elevation. You will be rewarded with 360-degree views but solitude will be elusive, unless you start early in the morning. Please note that parking and entry now require advance reservations.

Koko Head – 1.5 miles 1,200 ft EG

The hike to the top of the Koko Head crater is short but by no means easy. The 1,048 steps to the top of the crater climb 1,200 ft over less than a mile, which is quite steep. There is also a section of stairs with a big drop underneath. There is a bypass for it but that is also steep and a little scary. I took the stairs in that section on the way up but the bypass on the way down. The stairs are old railroad tracks that the military once used to transport equipment and supplies to the pillbox style bunkers on top of the crater. This hike is less crowded than Diamond Head because it’s more difficult, and it doesn’t require reservations. I loved seeing Hanauma Bay and Diamond Head in the distance as I was climbing. This hike seemed like a smaller version of the Manitou Incline in Colorado to me.

Pink Pillbox – 1.6 miles with 679 ft EG

This hike is also known as Maili Pillbox or Puʻu O Hulu Trail. It’s on the west side of Oahu, in Waianae off of Farrington Hwy. This is an under-rated part of Oahu that not many tourist come to. If you have extra time, be sure to go up the west coast until the road ends and get some poke from Aloha Poke. The hike itself is pretty steep but short. You will have fabulous views of the west coast on the way up. If you start super early like me, you might even encounter some wild goats! There are several pillboxes at the top, but I spent time exploring only the pink one. The rest of the time I marveled at the fabulous sunrise I observed at the top.

Lanikai Pillbox – 1.7 miles with 626 ft EG

This is the pillbox hike made famous by Instagram. Because the trailhead is in a neighborhood with no designated parking, finding a spot has become an issue. Be sure to pay close attention to the signs, don’t block driveways/other cars and arrive early. There are 3 pillboxes on this hike. Lanikai is the second one. I encountered many people here for sunrise, so don’t expect to have it to yourself even with an early start. Although it rained a little while I was hiking, the clouds did part for another amazing sunrise and I even saw a rainboW

Ehukai Pillbox – 2 miles with 275 ft EG

This is the pillbox hike I skipped and I wished I didn’t. It’s on the North Shore of Oahu and is best at sunset.

Makapu’u Lighthouse Trail – 2 miles and 500 ft EG

This is the easiest trail on the list because it’s paved! Parking can get busy but the views from the top are absolutely worth it. You will be looking North up the east coast of Oahu. You can combine this with Lanikai Pillbox if you have the time and don’t want to drive to this area on two separate occasions.

Skip: Manoa Falls – 1.7 miles with 633 ft EG

Manoa Falls was very underwhelming for me. The 150-ft waterfall was barely flowing when I was there. There were also plenty of mosquitoes that even bug spray did not deter. Add in the $7 parking charge and it’s all just a little too much. There is a beautiful section of the rainforest in the beginning and a random shipping container you go through, but those are the highlights. All the other hikes on this list are a much better use of your time.

One Comment on “Best Short and WFH-friendly Hikes on Oahu

  1. Pingback: One Perfect Day on Oahu - Balabanova All Over

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