Category Archives: Hiking

Your first Oahu hike


Your first Oahu hike

So, you finally made to Hawaii. Magic. And you want to go hiking on Oahu. There’s a surprising number of options. As someone who’s been hiking the island for decades, here’s my guide to deciding on your first hike, whether you are a beginner or a seasoned mountain climber. It (somewhat) assumes you are a tourist or visitor, and you’re staying in Honolulu. And I’ve left out a lot of details, you can Google the details of any of these trails for directions and the like.

Easy/Kids: Lanikai Pillbox Trail, Diamond Head, or Makapu’u Lighthouse.
Intermediate: Lulumahu Falls, Aiea Loop Trail, or
Advanced: Kuli’ou’ou or Olomana.

Easy Trails

Are you a relative beginner as a hiker? Want some great views without too much work?


Get yourself to the Lanikai Pillbox Trail. A short, 30 minute climb to some WWII pillboxes, concrete bunkers used for lookouts.

If you’re not staying on the windward side (few do), then make a day of it, combine it with a trip to Kailua Beach and a meal in downtown Kailua.

Pros: Short (30 min), Views (out of this world), Safe (wear real shoes though, don’t hike in your flip-flops (or “slippas”, as the locals would say — a friend broke an ankle as the trail is very eroded in spots).
Cons: You will be on this trail with a hundred new friends. Seriously. About 1000 people a day hit this. Don’t go on a weekend.

2. Hit Diamond Head. Another short (but steep) climb. Much of the “trail” is really concrete stairs leading to the lookout. But the views of downtown Honolulu are hard to beat.


Pros: Easy access from Honolulu, Awesome views. Doesn’t take long.
Cons: Crowded. Lots of concrete and stairs.

3. Makapuu Lighthouse trail

The Makapu’u area is awesome. Makapu’u beach is one of our favorite beaches on the island. Mostly a locals beach, great waves for bodysurfing, and not too crowded. The Lighthouse hike is an easy stroll with amazing views. It’s easily accessible from Honolulu (30 minutes from downtown), or from the Windward side. The trail is mostly paved, and you’ll get a amazing views of the famous Lighthouse as well as the entire windward shore. Do yourself a favor and combine this with a stop at Makapu’u beach and lunch at Keneke’s, a local plate lunch shop.


Pros: Quick & easy, awesome views, only “moderately” crowded.
Cons: Mostly paved. Somewhat crowded.


  1. Lulumahu Falls

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Lulumahu falls are also easily accessed from both downtown Honolulu and and the Windward side.

Head up the Pali Highway, near the top you will see a bunch of cars parked in a dirt area, right where Nuuanu Pali Drive runs into the Pali Highway. There’s an entrance there to the trail. Just follow the people :). The trail to the falls will take you maybe 45 minutes (assuming no wrong turns — the trail is not extremely well marked). The trail is ok for smaller kids who like to hike. If you have a bit of extra time the bamboo forest and the ruins of Kamehameha III make for an Indiana Jones style experience. To find the path to the ruins, stay to the right as you come into the bamboo forest. There will be a side trail (looks a foot or two wide) that starts a gap in the bamboo. Just follow it west through the bamboo and you’ll find it eventually :)).

Pros: Indiana Jones. Waterfalls. Nuff Said.

Cons: Can be crowded. Not hard to get off the trail. Not a sanctioned state trail, but tons of people on it.

2. Aiea Loop Trail.

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Pros: An ancient Hawaiian heiau (religious temple built from rocks). Gorgeous hawaiian Ohia flowers. A commanding view of the H3 highway and Halawa valley. A lost WWII bomber (I’ve not found it —  yet — but it’s there). Relatively flat, 5m round trip hike.
Cons: It’s not much of a workout, pretty flat. But fun


  1. Kuli’ou-’ou Ridge Trail


This trail is a workout. You start in a Honolulu neighborhood and end at the top of the Koolau mountain range, looking down into Waimanalo, with commanding views in all directions. Along the way you’ll go through a number of different “zones” of differing vegetation.

Pros: Great workout, amazing views, high quality trail.
Cons: A stairmaster section at the end. But it’s worth it.

2. Olomana

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Probably the best known Windward side hike. It’s not for the faint hearted. You’ll climb 1600 feet up a knife edge ridge, climbing with the assistance of ropes for 10–15′ in a few places. There are three peaks. The first is a workout but doable. The 2nd peak is not too much further, but you don’t get that much extra out of it, so I’d skip it. Don’t go to the 3rd peak. People die there. About once a year. Including experienced hikers. Just don’t.

Pros: Great workout, Amazing views, easily accessible.
Cons: Ropes. Mild danger. Extreme danger on 3rd peak. Just don’t.


  1. You will have heard of Stairway to Heaven, aka Haiku Stairs. I don’t advise it. The stairs have been heavily damaged by recent storms, and you’ll expose yourself to tresspassing charges and a fine. Not fun.
  2. The definitive guide to Oahu hiking is David Ball’s book, highly recommended.

The Hikers Guide to Oahu: Updated and Expanded (A Latitude 20 Book)

Experienced and novice hikers alike will benefit from the information in this updated and expanded edition of the best-selling The Hikers Guide to O’ahu. The author describes in detail 52 trails that will take you to O’ahu’s lush valleys, cascading waterfalls, windswept ridges, and remote seacoasts.

3. If you are a deeply experienced hiker and into extreme hiking, check out this site for (dangerous) adventures. (what I call “advanced” here, they call “easy” or “intermediate”. You have been warned.)


Hiking the Kamiloiki Ridge Trail

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Windward Oahu

Was going to hit the Makapuu Summit trail and look through the puka (that’s hole to you haoles). But, sigh, the trail is now “No Trespassing” (people not treating the mountain with respect and getting hurt on a trail where nobody needs to get hurt). So, I decided to try the Kamiloiki Trail that starts in the Hawaii Kai area of Oahu. This trail  is similar to Kuli’ou’ou Ridge Trail and Wiliwiliniu Trail (both of which I’ve hiked), in that it starts low on the Honolulu side and ascends to the ridge of the Koolaus, offering breathtaking views of the entire windward side of Oahu.

Key facts and tips:

  • 4.0 hours round trip to the summit, for me, a 50+ guy who’s done a fair bit of hiking and is in ok shape. If your legs are younger you can probably do it faster. I hit the trailhead at 9am in December and was back by 1pm. But, I spent an hour fooling around at the summit walking the ridge, you can do it less time if you need to.
  • Find the trailhead off to the left of the Heiau on Makahuena Place in Hawaii Kai, right next to the fence between the Heiau and the house nextdoor.
  • Much of the hike is overgrown – you’ll be walking at times in grass over your head with spiderwebs and such from time to time. Consider long pants (I wore shorts and was fine, but your mileage may vary). If you’ve got a bug thing, consider Kuli’ou’ou or Wiliwilinui if you want to get to the summit. In fact, if you haven’t done those trails, those are better  to do first.
  • It’s hot with not much shade. I brought 2 liters of water and drank it all.
  • Watch your step. Much of the trail you are walking in tall grass and can’t always see your feet, especially if you are on the lookout for spiderwebs. It’s easy to trip. Sprain an ankle up there and it’s a helicopter ride for you. And when you get to the top, please don’t be an idiot and fool around. Pay attention. People fall off up here and die.

The trail starts near a Heiau (an ancient hawaiian rock structure that had religious purposes). The Heiau is nestled right at the end of a residential cul-de-sac on Makehuena Place. Just sitting right there. Very cool.

The trail is a little hard to find – when looking at the Heiau, walk to the fence that borders the house on the left. Keep walking along the fence and you will find the trail – it’s a bit overgrown as of this writing (Dec 2015), but still visible.

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The grass is as tall as I am.

In contrast to both Kuli’ou’ou and Wiliwilinui, this trail is not used much (I saw no other person on my hike), and the trail is pretty overgrown, especially near the bottom. Pay close attention to ribbons strung from the trees – but in spite of that you’ll feel like Indiana Jones bushwhacking through the forest for the first half mile or so.  Then you’re up on the ridge and trail is much easier to follow, as it runs right up the ridge. It’s still pretty overgrown though. From the ridge you’ll quickly have great views of Honolulu, the ocean, and the back side of Koko Head.

About 2/3 of the way up, you’ll come out of the scrub and tall grass and into 3 shaded groves of Ironwood and Pine with a carpet of pine needles.

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Ironwood Grove

The shade feels wonderful and it’s nice not to be wondering how many spiders I acquired in the last hundred yards (none, as it happens). These three glades are your warning for the final ascent. The trail is a little hard to follow here, I picked the trail up off to the left after the 3rd glade. From there, you scramble up some inclines and into what looks like a small creekbed or water run off. Up, up, up, no switchbacks to break it up. In 30 minutes or so you’ll see blue sky break through, and then you are onto the ridge.2015-12-07 12.06.01

From the ridge you have breathtaking views of Waimanalo and the entire windward side of Oahu. From the ridge if you follow the trail to your right, in about 50 or 100 yards you’ll come out on another peak, where you have an amazing view of Makapuu Beach, Makapuu Lighthouse, and various Civil Defense radio towers and the area where the infamous Dead Man’s Catwalk is located. Not wanting a brush with local law enforcement, I decided to skip that part of the tour.

2015-12-07 11.18.00A powerbar and some water, and then back down the trail. Down is easier than up. But then you knew that. Without time for pictures and such at the top, you can do it in 2 hours up and 1 hour down.

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Rabbit Island looking back towards Makapu’u.

It’s right under your nose…

Ancient castles set in lofty cliffs. (Game of Thrones, right?). Mountaintop signal fires communicating to settlements a hundred miles away. (Lord of the Rings movie, right?). Ancient roads running miles in a straight line, now hidden to all eyes except experts. And supporting a system of empire and tribute. (Ancient Rome, you’re thinking…). Hybridized Corn. (X-files, anyone?). Ritual cannibalism (New Guinea?). Pottery that will steal your breath it’s so beautiful. (Ancient Greece?). Use of geologic features and stone construction to support Astronomical events guiding religious ceremonies? (Stonehenge???). Underground rooms, home of rituals and dances, and settlements lost in the wilderness for a thousand years, found pristine by ranchers looking for lost cattle…..all this and more is right under your nose here in America, in the southwest near “4 corners”, where Utah, Colorado, New Mexico and Arizona meet, the home of the Chaco culture, aka the Anasazi, aka “the Ancestral Puebloans”, as they are now called. It’s amazing how many Americans don’t know about this truly unique aspect of the history of the country they live in.

We’re just back from a duo of great trips. The first was my daughter’s wedding, which was simply awesome. Enough said.

Immediately following, Michelle and I went on an exploring trip with our old friends Thomas Jensen and Lynn Thorsen-Jensen. Both accomplished tech executives, published fiction writers, fencers, and amazingly well-versed historians. It’s enough to give a person an inferiority complex. Thomas in particular seems to know everything there is to know about English history (especially the medieval period), as well as being a near-expert (and I’m not sure about the qualifier) on the history of the ancient Southwest, the purpose of our trip.

We saw an amazing set of things. Flying into Durango, we were wisked off to Mesa Verde, home of the most famous of cliff dwellings, Cliff Palace (which is closed for renovations). First up is Balcony House. A couple of ladder climbs (30′ and 60′ !!!) later, we’re looking out over the valley from our own cliff house. Amazing that people lived here. Indiana Jones features: a tunnel leading both into and out of the cliff-house – this would not have been easy to attack, and indeed it’s believed that the move into cliff houses (from the mesa top) was primarily a defensive move, during a time when drought made competition for food an ugly business.

Through a happy set of circumstances, we were able to get a tour through Square Tower House, only open 5 times a year. Underneath a huge cliff overhang, with a natural water flow into the compound, Square Tower is an incredible fortress. (see the crow’s nest up there?).

Then it’s off to Spruce Tree House, and enormous complex with 130 rooms that goes back into a cave nearly a small city-block. And had 130 rooms and 8 kivas (underground rooms for ceremonies and living space.)

After doing more hiking and touring, we’re off to Hovenweep, one of the loneliest places I’ve ever been. (Hovenweep is Ute for “deserted valley”, so it seems appropriate). The Anasazi fled here from Mesa Verde and other places, fleeing the drought and conflict from further south. I’ve been here twice, and the first time I was literally the only one there, miles and miles. Closest I ever came to hearing ghosts. This time, the sun is up, and I have people with me. A bit less spooky but still amazing. And it’s spring in the desert – I’ve been out here a lot and I’ve NEVER seen the flowers like this before. And lots of turkeys! The Anasazi kept domesticated turkey as a food source.

Finally we’re off to Chimney Rock. Settled in the early 900s, a Chacoan Great House was built on the peak likely near 1076 AD, as the northernmost outpost of the Chacoan empire. I used the term empire advisedly as not every agrees there was an empire. But it seems likely. It’s established that signal fires, smoke and mirrors were used to communicate between the Great House and Chaco canyon 85 miles away ( And the imposing presence of the Great House at the top of the mountain, when green and fertile river earth was available in direct sight, clearly indicates an imposing presence (military / religious empire?), rather than simply a good place to live. In addition it’s also established that the moon rises between the twin spires of Chimney Rock every 18.6 years during the Lunar Standstill, likely guiding religious ceremonies as well as planting seasons. (

Finally, after our fill of ancient history, we’re back to the “modern” era – a last night at the Strater Hotel in Durango. The Strater is a old west hotel – the Diamond Belle saloon, period furniture and history of unique guests. Louis L’Amour wrote a number of his novels here. We content ourselves with a last night of bridge (we’ve been playing every night and I’ve been getting cards like I’ve never seen before). The hotel graciously finds us a room in the basement to play – wow – it’s filled with green velvet, vintage photos and mirrors – I feel like I’ve wandered onto a an old-west poker movie set. And, there’s a bluegrass band warming up next door. Too cool!

Struggling with a conundrum? Looking for insight? Take a few days off. The answer might be right under your nose….

And if you want insight into the Ancestral Puebloans, you could do much worse than House of Rain, by Craig Childs.

The Snow Leopard, by Peter Matthiessen

Mourning the loss of his wife to cancer, Peter Matthiesen joins George Schaller on a trek to Nepal to study the Himalayan blue sheep and in hopes of glimpsing the rare Snow Leopard. His trek will take him from the slums of Varanasi to the roof of the world, both literally and figuratively, in Nepal.

Part contemplative travelogue, part Buddhist primer, The Snow Leopard reminds me often of [Zen and the Art of Motorcycle Maintenance], with the constant switching between observant travel writing and the pursuit of deep ideas. But it has a lot more zen than Pirsig’s book. He has a way of writing about Zen that encompasses both the deep philosophy of Zen and the esoterica that surrounds it, but also captures Zen in the daily moment:

My foot slips on a narrow ledge: in that split second, as needles of fear pierce heart and temples, eternity intersects with present time. Thought and action are not different, and stone, ice, sun, fear, and self are one. What is exhilarating is to extend this acute awareness into ordinary moments…for this present – even while I think of it – is gone.

The Snow Leopard is a deep book, by turns joyous, philosophical and melancholy. Matthiesen’s preoccupation with death runs through the book, starting on page 2 as he crosses paths with a dying old man in Varanasi.

The old man has been ravened from within. That blind and greedy stare of his, that caved-in look, and the mouth working, reveal who now inhabits him, who now stares out.

I nod to Death in passing, aware of the sound of my own feet upon my path. The ancient is lost in a shadow world, and gives no sign.

Matthiesen’s writing is evocative throughout. “There are no roads west of Pokhara, which is the last outpost of the modern world; in one day’s walk, we are a century away“. If I measure my interest in a book by dog-eared pages, my copy of the Snow Leopard might be one of my winners. Every 10 pages there’s something I marked when I read it. The book is all omens, dreams, portents, and deep thoughts, interspersed with the day to day minutiae of hiking, wet boots, blisters and snow blindness, together with encyclopedic descriptions of flora and fauna of his trip. He captures the dynamic of being on the trail with someone for an extended duration perfectly. After a particularly exhausting climb one day on a cliff, Schaller says something only mildly annoying, and Matthiesen remarks, not entirely joking one suspects, “How easy it would be to push him over“.

While The Snow Leopard is a book about a journey with an objective (seeing the Snow Leopard), as is usually the case, the journey IS the objective. It is a gorgeous book. If you have any interest in zen, hiking or travel, read it.

A day in Marin county and the Palomarin trail

Had one of my regular visits to California for work, and managed to spend a weekend with my daughter and her boyfriend. Friday night we went to a nearby bar in San Francisco (Paragon, a great place), to watch the Red Sox in the NLCS. We were planning on taking a trip to Marin County for some hiking, but weren’t really sure where we were going.

Paragon proved to be a source of many co-incidences. Waiting outside the bar (which didn’t open til 5:30), happened to be someone living in SF but who grew up the a few towns away from where I live in Massachusetts. Shortly they were followed by a horde of red sox fans. Game on! Sitting at the bar, some Detroit fans joined, sitting next to us. We had some friendly conversations – they were actually from Marin County, and recommended we hike the Palomarin trail. I’d been thinking about that as one of many choices but their recommendation confirmed that as the plan. As the game went on the Detroit fans were replaced with a different couple. Turns out, one of them worked in tech, and both my daughter and I had a number of number of mutual acquaintances. Weird. Last but not least, the Sox came through in the end with grand slam by Shane Victorino to win the game and head to the world series!

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Next day we headed out to Marin. We drove to the Palomarin trail, about an hour and half from downtown San Francisco. After heading around the Bolinas Lagoon, you’ll drive down a dirt road (passing the Point Reyes Bird Observatory along the way), continuing 10 minutes or so after that to the trailhead.

IMG 2773The trailhead has restrooms (as does the bird observatory). When we were there the trail was well used but not over-crowded (there was what looked like a teen venturing group headed out to camp on the beach as well as many hikers and trail runners).

The trail is about 9 miles total (4 1/2 miles each way). It’s relatively flat, about 600 feet elevation gain over all. We hit the trail around 11am or so. The trail starts in a grove of fragrant eucalyptus trees, then opens onto a mesa with wonderful views of the ocean.
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The trail continues to follow the ocean for awhile, then turns inland. You’ll briefly go through a variety of ecosystems including an almost rain-forest like section, pines, another foggy mesa, a rocky pass that would have felt at home on a greek isle, and finally a few mountain lakes (there were some folks swimming the day we went).
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After about 4 miles there’ll be a spur trail to the left (there’s a sign) that will take you down to Alamere Falls. The spur is about 0.4 miles long. Other blogs have mentioned poison oak, but we didn’t have any trouble with that.

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At the end are a wonderful series of small waterfalls and pools. Then there’s a mildly tricky rock scramble down onto the beach. Then, your prize from your labors. A neat, moss covered waterfall, 40 or 50 feet high. And waves crashing on the beach, seals and birds in the water. A great place for lunch! Then we’re back on the trail and back in the parking lot by about 2:30. On the way back you’ll get gorgeous views of the coastline, you didn’t notice on the way out because it was behind you 8).

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From there we headed up through Point Reyes and on to the Tomales Bay Oyster Company. IMG 2843It’s kinda out in the middle of nowhere, but well worth the drive. You buy your (raw) oysters from them. Everything else is up to you. There’s picnic tables and grills, you can each your oysters raw, grill them, or both. You’ll want to bring picnic supplies (we brought Brie, crackers, fresh avocados for guacamole, and other goodies. It’s kind of a motley crew there – we bought extra orders from the Sacramento Assassins, a friendly bunch of motorcycle riders down from the day. The staff is friendly and helpful and with a location right on the bay in the sunshine, it couldn’t be more beautiful.
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We stopped on the way back in Point Reyes for some book shopping, my addiction, at Point Reyes Books, while sipping on some great coffee from next-door, the Bovine Bakery.

All in all a classic Marin County late summer day.

(more photos here: