Looking for the best trails around Kailua?

Explore the best rated trails in Kailua, HI, whether you're looking for an easy walking trail or a bike trail like the Ka'ena Point Trail and Keoneula Boulevard Bike Path . With more than 12 trails covering 33 miles you're bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.

Recent Trail Reviews

Malaekahana Bike and Pedestrian Path

Great link between Laie and Kuhuku

April, 2024 by daviddemartini

Great trail for cycling or walking. It’s off Kam hi way and has a nice open country feel. From Kuhuku I continued on down the road shoulder to Turtle Bay.

Ka'ena Point Trail

spectacular Ocean &Mountain Views

July, 2023 by reggie.flesvig

This is my favorite Oahu hike. The ocean and tide pools are amazing and your walking right along the mountainside. We hiked from Ka’ena State Park and went all the way out to the western-most point of Oahu. Free, ample parking is available in the park at the end of the road. Lock you car. Closed toe shoes are a must as the trail is rocky. Bring plenty of water as it is a hot, dry hike. The trail is 99% flat with one up-and-around that is a bit challenging (see photo).

Pearl Harbor Bike Path

A perfect representation of Oahu

July, 2023 by seanymcsean

I’m seeing a lot of reviews about the houseless community on the trails. To the folks leaving those reviews, are you doing anything to help?

I enjoy riding this trail w the 9 year old that I mentor. Beautiful views of the harbor, cool neighborhoods, old farms, houseless communities… golf courses (the irony). I’ve never once felt anymore unsafe then anywhere else in Pearl City.

Highly recommend for a unpolished representation of this beautiful place that we get to live.

Accordion

Waialua Beach Road Bike Path

Great route to cycle to Haleiwa

March, 2022 by malcolm_fawcett

A nice safe route (even in the dark) to get to Haleiwa town center. The bike trail ends at the traffic circle before you get to Haleiwa but there is sufficient pavement on the left hand side to allow you to cycle safely from that point into Haleiwa. Best to take it easy, as we encountered quad bikes, motocross bikes, cyclists, joggers and pedestrians along the trail.

Ka'ena Point Trail

Great walk with some amazing sites

March, 2022 by malcolm_fawcett

We walked from North Shore trailhead to Kaena Point. Easy walking but recommend closed toe shoes and plenty of water. We were lucky enough to see the Laysan Albatross performing their mating dance and soaring through the skies. At the Point we saw three Hawaiian Monk seals and another had just landed at 10-minute beach. With mountains on one side and big surf on the other it was a breathtaking walk, we’ll worth the effort.

Ala Moana Park Path

Ala Moana

October, 2021 by jaleonard9

Beautiful oceanfront park with awesome views, it is very popular with locals. There are many paths, however some have holes, cracks, etc. The beaches off protected ocean swimming.

Ka'ena Point Trail

Sunny, breezy good fun

March, 2020 by mcvinneys

Great trail for those just out for an adventurous afternoon walk. The old railroad was turned into a hiking path that varies in width from 4 to 12 feet. A little bit rugged in some places as volcanic boulders litter the path. I think the park people do that on purpose to keep trucks out. In one place the trail is washed out and a sort of billy goat trail gets you by for a hundred yards. There are no railings or ropes along the cliffs so watch where your children are running around and don’t back up to get that perfect shot. That said, I saw kids as young as 7-8 on the trail. Mainly level the whole way. From the parking lot at the end of Rt 93 it’s about 2.25 miles to the point. Bring water and wear a hat. Don’t forget your sunscreen as you’re getting the rays directly plus indirectly off the water. You’ll have fun on this walk so enjoy the day!

Pearl Harbor Bike Path

update on Pearl Harbor trailway

June, 2018 by seakayaker

This used to be such a nice, safe ride, but with all the homeless and increase in crime, do not recommend this pathway to the East Loch. You are better off riding at Ala Moana, but then again, it is quite crowded with tourists.

Kailua and Kane'ohe have some nice areas to ride. Happy Trails.

Ka'ena Point Trail

How can I describe this

November, 2017 by thomasmarquette

It's my first time out mountain biking but I found this trail too difficult for a bike. At least with my level of experience. It looks easily walkable.

Pearl Harbor Bike Path

ran from work to home

September, 2017 by tavina8884

I tracked the distance on my run and only came up to 7 miles not sure how they came up with 10. Did encounter three areas with a handful of homeless, but they kept to themselves, no biggy. There are about 3 miles with absolutely no shade, so the heat at 4pm was a challenge. The are around The Neil Blaisdell park was very pretty even had a water fountain. The best thing about this trail is that it allowed me to run from work all the way to Waipio.

Pearl Harbor Bike Path

Don't bother with this trail

June, 2017 by dustinlevalley

I started by the entrance by the base. The very first thing I have noticed was the homeless camps set up under an underpass. I kept riding a few more miles thinking it would improve and it was like that the whole way, nothing but homeless camps, sewage, garbage piles and very rough pavement. I was on a penny board and there was some spots I had to get off and walk a couple hundred yards until I found a decent patch of pavement. There was nothing scenic about this trail.

Pearl Harbor Bike Path

Commuter run

June, 2017 by steve.larsen0804

I commute from Royal Kunia to the airport, picking up the PHBP at the Waipahu dump to the end at Kam Highway near Pearl Harbor Memorial. As others have said scenery is not great, there are a couple homeless camps (some have been decorated really nice), a lot of street urchins fishing next to the contaminated seafood signs and of course a small sewage plant. It is not for sightseers although it does take you near the Navy's boneyard in Middle Loch if you like old ships.

But the trail is generally safe, most peds will give way if you ring a bell and it makes quick work of the worst transit chokepoint on the island. My ride is often as fast as a drive would be when traffic is backed up.

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