We nearly always hike alone, but we changed it up a bit this time! We were researching trails on Saturday night when we found out our good friends were also planning to head out on Sunday morning. When they suggested Keālia Trail, we checked it out and asked to join them!

This trail is near Dillingham Airfield towards Ka’ena Point on Farrington Highway on the North Shore. It’s rare that we don’t head windward for a hike, so this was a nice treat. And this was only our second time exploring the Wai’anae Mountains. (The first was a short walk with the YMCA at Camp Erdman.)

Once you pass the runway, you’ll see an opening that displays the ‘Keālia Trail’ sign. You’ll turn left and follow the drive around until you see another trail sign with instructions on where to park.

We unloaded from our minivans and got ready to go. They have three children like we do, but one of theirs is a toddler. That means he gets carried. The dad is a beast!

Then it was time to get started! The first bit is just a flat road. I think it’s there to lull you into a false sense of ease about the upcoming switchbacks. DSC02458 DSC02459 DSC02462 DSC02464 Our girls were born just a few days apart, and they have become incredibly good friends in the last few months.DSC02465 After just a bit, the fun really began. We didn’t see any falling rocks, but I’m always thankful for the warning!
DSC02468 DSC02471 Audra took a little shortcut that ended up taking longer than the normal path would have.DSC02479 We didn’t count the switchbacks, but at some point, we came into a bit of exposed path. (Supposedly, there are 19 altogether though.)DSC02481 DSC02485 Even if there is an easy way to walk, Austin always finds a harder one.DSC02495 It got a little steep in parts, but it never really felt scary.DSC02496 Love this kid and his facial expressions!DSC02498 And Miss M – she didn’t want to pose for me at all. It’s alright though. I love these shots too.DSC02502 Even with the pack, he was still out ahead! I don’t think I adequately explained my slow speed to him prior to the hike.DSC02503 DSC02505 I couldn’t decide which one of these to share of E and I, so you get both. How gorgeous is that ocean?!DSC02511 DSC02512 I love this girl!
DSC02513It took us about an hour to make it up to the end of the Keālia Trail. The end was marked by a nice flat pine-needle-y area near a covered picnic table. So we stopped for a snack.


Just like his sister, I got a shot of D, but on his own terms. Works for me!DSC02519

Sibling love.DSC02523

So at this point, you could turn around and head back. But we’d read about a great lookout that was at the end of this dirt road. We didn’t really know how long the access road was, but we were all on board.DSC02526


It became a pretty steady incline, and the men weren’t interested in taking it slow. Can you see them? They were waaaaay up there.DSC02530

The boys had a good time chatting.DSC02536

Austin found some sticks and couldn’t resist playing with them. DSC02538

The girls took their sweet time. The road ended up being a lot longer than we anticipated. It was tiring.DSC02540

Love this shot of E and M!DSC02544

Kuaokala Trail is a separate path you can take, and the lookout is just up the hill from the trail sign. There’s access to this trail from the Wai’anae side, but it requires a vehicle with 4WD and a permit.DSC02595


According to our GPS, the trek in was a bit over 4 miles. I’m not sure if that’s accurate, because another site said it was 5 miles roundtrip. But our Fitbits all concurred with our estimation.

But the view of Makua Valley? So very worth it.


There was another group that reached the lookout just behind us, so we left them to it and went back to a safer point so little L could run around and we could have a snack.

But then we went back so we could all get our pictures.DSC02560e




A panoramic shot. I really didn’t do it justice!DSC02576e

The boys had some fun back at our ‘safe spot’.DSC02580

Then we switched off with the baby and got more pictures.DSC02583eDSC02590e

And then it was time to head back down. Downhill wasn’t difficult really, but it was slippery in parts. I’m still learning to trust myself not to fall. Until then, I’m as quick as an elderly turtle.DSC02593




But we made it back to the picnic table eventually. That’s a good looking group right there.DSC02609

And then we hit the switchbacks again. Not exactly the most fun, but the views of the north shore were pretty.DSC02613

We were just a wee bit behind OB, L & Austin.DSC02614

Love this lady.DSC02618e


By this point, she had already changed her mind about this hike roughly 5 times. She hated it, then she loved it, then she remembered the switchbacks and hated it again, but then she looks pretty great here.DSC02620

Aidan got my scaredy-cat gene, but he has come so amazingly far. Even if going up is difficult, he just rocks it on the way back down. Once he feels familiar with an area, he has less fear. He’s learning to trust himself in a way that makes me so proud. I hope to learn from him!DSC02626

The hike went a bit longer than we planned, so poor James missed the beginning of the Colts game (we’re from Indiana). So in between the slippery spots, he checked his phone for updates.DSC02631

And then we were done. I don’t know who was happier to be done with the hike – L or his dad. I can’t imagine carrying around a toddler for 5 hours! As we were walking out, L decided to grab all the rocks he could find for souvenirs. And he couldn’t be rushed. It was adorable.DSC02639

As we were leaving, we asked a fellow hiker to grab this shot for us. It was E’s idea, and it turned out so beautifully. DSC02646e

So 5 hours and a little over 8(?) miles later, we were exhausted but filled with so much joy about a great day together. This was our longest hike with the kids, and I was super proud of how well all of them handled it.

This hike is pretty kid-friendly, and I love that you can tailor the distance to your family’s preference. You could even do Kuaokala Trail if you were feeling super adventurous and energetic!

Hamama Falls Trail
Hanauma Bay Hike & Rock Bridge