Best Hikes On Oahu: The Pillbox Trail (Ka’iwa Ridge)

Basic Information

• Name: Pillbox Trail
• Where: Kailua, Oahu
• Distance: 1.7 miles (one way)
• Elevation Gain: 822 feet
• Time: 1-2 hours
• More Information: Yelp.com

Topographic Map of Pillbox Trail

Google Map of Pillbox Trail

Narrative

One of the most popular hikes on Oahu that I recently completed was the Pillbox Trail.  This hike which is also known as the Ka’iwa Ridge hike I would find out is popular for good reason.  The trail is located in Kailua on the Windward Coast of Oahu.  The trailhead is accessed from the posh Lanikai neighborhood:

Before tackling this trail I decided to recon the parking situation in Lanikai the day prior before driving to hike up another trail on Oahu’s Windward Coast.  As I passed the Lanikai Beach Park at about 9:00 AM I could see all the parking was filled up.  I then drove into Lanikai and could see that it was a parking nightmare with people fitting in their cars in any open spot they could find.  As beautiful as Lanikai is it must be a nightmare dealing with the crazy parking situation in that neighborhood every day.  I decided I would wake up early and get to the trailhead at 6:00 AM in the morning to make sure I could find parking.  As it turned out the parking situation was not much better; the Lanikai Beach Park was completely full forcing me to drive into Lanikai to find parking.  Fortunately I found an open spot at a small park in Lanikai not far from the trailhead.  From there I walked up to the trailhead located on Kaelepulu Drive:

I had read the trailhead is hard to find, but it is actually quite easy; just walk up the road to the Mid-Pacific Country Club and across the street follow the small access road towards the hill where this trailhead sign is located:

The other option to find the trailhead is to just follow the crowd of people heading that way.  From the trailhead is where a highly eroded path up the side of Ka’iwa Ridge begins:

Considering the amount of foot traffic this trail receives it seems the City of Kailua should invest some money into constructing a properly maintained trail:

Fortunately it did not rain the prior night on Kailua thus causing the trail to be dry.  I could see how a wet trail could be a frustrating and slippery mess to ascend.  The first section of the trail is also quite steep and I passed a lot of people who were slowly making their way up it.  I don’t mind steep trails because that means I gain elevation more quickly.  Before I knew it I was high up on the ridgeline with stellar views looking over Lanikai with the Mokulua Islands in the distance:

To the north I had a good view of Kailua and the golf resort down below:

Here is a panorama of Kailua from the Pillbox Trail:

Even though I already had good views I still had some elevation gain to make to get up to the first of three bunkers along the Pillbox Trail:

Up on the ridgeline the trail was much better than the initial steep climb, but it had a few rough section that would be a sloppy mess to hike up if wet:

Here is the final approach to the first bunker:

The pillbox bunkers along this trail are a legacy from Hawaii’s World War II past.  After the initial attack on Pearl Harbor there was a general fear that a landing operation would be next by the Imperial Japanese.  The US military turned Oahu into “Fortress Hawaii” due to the fact that it was the island where it was able to project military power from.  All around Oahu abandoned bunkers can be seen on prominent ridgelines like this.  Even the world famous Diamond Head Crater is covered in bunkers.  On the final approach to the first bunker there are a few rocky sections that I had to be careful ascending, but nothing difficult:

Here is a picture of the first bunker which my Garmin Fenix had as being 527 feet above sea level:

Speaking of the sea, the view from the first bunker was amazing:

Here is a closer look at the Mokulua Islands which were quite a sight:

In the distance to the south I could now see Makapu’u Point:

At the below link you can read about the great hike I took to the lighthouse on Makapu’u Point:

• Best Hikes On Oahu: The Makapu’u Lighthouse Trail

I did not spend too much time at the first bunker and continued to follow the horde of hikers up to the second bunker:

The walk over to the second bunker was pretty easy:

The views at the second bunker were just incredible:

Here is once again a closer look at the Mokulua Islands:

Here is a panorama of the view:

I spent more time soaking in the views from the second bunker which while still crowded was not as bad as the first bunker.  After about 10 minutes I began to survey the rest of the route along the Ka’iwa Ridge:

At the very end of the ridge I could see a prominent pointy hill with a trail running down the front side of it back into Lanikai:

I decided that was the direction I would go and continued down the trail away from the second bunker:

After the second bunker the Pillbox Trail becomes much more overgrown:

The trail was still easy to follow, but I could tell that few people hike pass the second bunker.  In fact I saw one other hiker during the timeframe I hided pass the second bunker despite the mobs of people hiking up this trail.  Here is a picture looking back at the second bunker where some of the hiking mob could still be seen:

Here is a panorama that shows the second bunker on the left with the Mokulua Islands in the distance:

Here is another panorama centered this time on the second bunker:

Despite the overgrown trail I was actually moving much quicker now since I did not have to stop to let people go by me or get stuck behind slower hikers:

I next came to the third bunker on the Pillbox Trail which I had all to myself:

From the third bunker I had much better views compared to the other bunkers of the area to the south of the Ka’iwa Ridge:

Here is the view from the third bunker looking down towards the final stretch of the Pillbox Trail:

I could also see the rugged slopes of the Ko’olau Range covered in an early morning cloud cover:

Directly across from me the very steep Olomana Peak which is considered Oahu’s version of the Matterhorn due to the difficulty of climbing it:

After spending about five minutes taking in the views I continued down the trail as it descended towards the last major hill along the ridgeline:

Here is a picture that shows the view looking back towards the highest hill where the second bunker was located on:

It also would not be a hike in Hawaii without spotting at least one rainbow:

After a short, but steep final stretch I found myself on top of the final hill that appeared that it may have also had a bunker on it at one time as well:

The hill of course had yet another view of the Mokulua Islands:

Here is a closer look at these two islands:

I could also see the entire Ka’iwa Ridgeline that nearly encircles Lanikai down below me:

Here is an even wider angle panorama of the view:

On the opposite side of the hill I was able to look down into Bellows Air Force Station:

The base is Morale, Welfare, & Recreation (MWR) facility for the US military in Hawaii along with being a Air National Guard facility.  The base has a beautiful beach and small bungalows for US military servicemembers and veterans to rent:

After I finished taking in the views are started the steep descent down the hill and back into Lanikai:

I had to very careful with my footing here.  Fortunately there were plenty of trees to hold on to help keep my balance as I descended the hill.  After a short descent I found myself exiting the Pillbox Trail and back into the Lanikai neighborhood:

The trailhead on this end of the Pillbox Trail is located at the intersection of Luika Place and Poopoo Place:

From the end of the trail I measured the complete traverse of Ka’iwa Ridge as being 1.-7 miles long.  Due to all the pictures I was taking it took me 1 hour and 15 minutes to traverse the ridge.  After completing the traverse I still had to get back to my car parked near the trailhead.  I decided to go ahead and do a jog through the Lanikai neighborhood.  Fortunately Lanikai has one major one-way loop road with a wide bicycle lane to jog in:

While jogging down the road I got a good laugh at seeing this car of someone who is a serious Raiders fan:

I also had some nice views of Ka’iwa Ridge that I had just hiked that were soaring high above :

Here is a closer look at the second bunker on the highest peak above Lanikai:

During my jogged I also made sure to stop and walk down one of the beach access trails:

Here is a closer look at the sign highlighting the rules for Lanikai Beach:

Here is the view of the coastline bordered by multi-million dollar homes:

Once on the beach the views of the Mokulua Islands in the early morning light was almost mesmerizing to see:

Here is closer look at both islands:

Conclusion

Normally I tell people to get to a popular location in Oahu early to avoid the crowds.  With the Pillbox Trail it almost doesn’t matter because even early in the morning there are crowds hiking up the trail to watch the sunrise.  For anyone wanting to get away from the crowds do what I did and hike pass the second bunker.  I almost had the entire ridgeline pass the second bunker to myself.  However, hiking the entire ridge had turned what is normally a 2-mile round-trip hike in to a 3.7 mile hike instead.  I did not mind the extra mileage and thoroughly enjoyed the hike.  The Pillbox Trail is popular for good reason and I highly recommend that everyone check it out, that is if you can find parking first.