Looking for some moderate or challenging day hikes on Oahu? Below is a list of some moderate and challenging hikes. Some are challenging due to steepness, others because of the condition of the trail. Either myself or close friends have completed the hikes listed below. There are many other challenging hikes on Oahu, please use caution on trails that are unmarked and/or cross into trespassing zones. Googling “challenging hikes on Oahu” will also bring up a host of hikes where you can be cited for trespassing. Do your research before heading out and make sure you bring supplies. These are not hikes to attempt on your own.
Koko Crater Trail
Length: 1.8 miles Elevation Gain: High Terrain: Little shade, dry and Hot Parking Lot: Yes
Also known as the “Koko Head Stairs”, this 1.8 mile (1,050 steps) out and back trail will test your endurance and strength. This trail takes you along the abandoned railway that used to lead to a pillbox bunker at the top of Koko Crater during WWII. You can park at the Koko Head District Park. The trail starts out easy, but gets progressively tougher. One of the tough things about this hike is that it follows the railroad ties straight up the crater, with an area where you have to cross a “bridge” with a steep drop below. If you make it to the top, you are treated to gorgeous, panoramic views of Hanauma Bay and Pork Lock Peninsula.
Olomana Trail
Length: 4.4 Miles Elevation Gain: High Terrain: Wet, some shade Parking Lot: No
Also commonly referred to as “three peaks”, this is a trail to make sure you are well prepared for. Do not attempt this trail if it is currently raining, is going to rain or rained the day before. There is no parking at the trailhead, check out All Trails for information on finding street parking. The trail is accessed from the intersection of Maunawili Road and Auloa Road. Mount Olomana is the first peak, and is about 1.5 miles up the trail. It offers wonderful views of the Windward side of the island. You can continue on the trail to the second peak, but it is not recommended to continue on to the 3rd peak, as it is extremely dangerous. Be aware that there are steep drops and rock climbing throughout this hike. While there are ropes tied along many of the steep and rock climbing portions, only experienced hikers and climbers should attempt this hike. When I hiked to the second peak in 2014, I actually brought along my own guide rope and climbing shoes in case they were needed (they were not). This is an exhausting but rewarding hike that is best tackled with a small group.
Maunawili Falls Trail
Length: 2.4 Miles Elevation Gain: Moderate Terrain: Tropical, Covered Parking Lot: Street Parking
If you are looking for a fun trail to a waterfall that you can jump off of, look no further than Mauanawili Falls Trail. The difficulty with this hike comes from walking over eroded tree roots with some muddy areas. There are areas where there are steep man-made steps as well as boulders. At one point in the trail there is a small fork: after climbing up a few steep stairs, where you will reach a brief plateau, make sure you follow the trail down to Maunawili Falls. When you get to the falls, you will see the falls and the pool area. Many people will swim in the pool and jump off the rocks. However, be aware that there are dangers with taking this jump and swimming in the water. Some water and streams may be contaminated with leptospirosis bacteria, as well as the dangers of jumping into water.
Length: 4.4 Miles Elevation Gain: Moderate Terrain: Varied, Forest through open ridge Parking: Street Parking
This is a moderate to challenging hike that travels through a variety of environments. The trailhead is located in a residential area, at the end of Kalaau Place. Please be considerate of the residents if you street park. While the trail is 4.4 miles, it can take 5-6 hours to complete, depending on your hiking speed and due to the rocky terrain and steep inclines. There are a few places along the trial where you get gorgeous views, first of the Kuliouou valley, and then of the Kailua coastline and Koko Crater. I completed this trail in 2017 as part of a hiking challenge, while carrying my toddler in a hiking backpack. I recommend leaving young kids at home for this one, but older children who are experienced hikers might enjoy it.
Length: 7 miles Elevation Gain: Moderate Terrain: Forest, Muddy Parking: Laie Park
This is part of the Laie Ridge Trail, also a moderate hike! This trail gives you the views of a ridge trail mixed with a two-tiered water fall. This hike is on private land, and you should request a permit from Hawaii Reserves, Inc. As of this writing, it does not look like Permits are being issued due to safety concerns over a dog attack, however, check their website for more information regarding hiking permits. One of the trickiest parts of this hike comes from the descent down to the falls, there is a rope to help with this descent, and it can be dangerous when muddy.
If you are in for a longer adventure, complete the 12 mile hike on the Laie Ridge Trail. This is a strenuous ridge hike that merges off from the Laie Falls Trail and connects to the Ko’olau Summit Trail (KST). For more information about connections and segments of the Ko’olau Summit Trail, read this article about completing the trail from North to South.
What are some of your favorite hikes on Oahu?
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