Family Hikes on Oʻahu’s Windward Side – A Local’s Guide to Easy & Adventurous Trails

Explore Oʻahu’s windward side with these family-friendly hikes ranging from easy strolls to adventurous climbs. From waterfalls to pillboxes and jungle trails, this local guide highlights the best trails for every age, plus what to pack, safety tips, and where to eat after your hike.

Oahu Family Hikes for all Adventure Levels

If you’re on the hunt for Oahu family hikes, I’ve got your back. I’ve taken (ahem, dragged) my kids on hikes since they were babies so let’s dive in and explore some options on the windward side of the island. If you’re staying in Waikiki and want to stay close, this post lists family hikes on that side of the island.

Below I have family favorite hikes unofficially ranked from most adventurous – with a rating of “5” – to least adventurous with a rating of “1” (one being more of a stroll than a hike). Pick an adventure level and let’s go!

Crouching Lion Trail, Ka’a’awa: Level 5

Crouching Lion is a short but intense, slippery scramble to an outcropping with coastal and valley views. Big drop offs make it a hike best suited for older kids who are comfortable with heights.

Lanikai pillbox trail – The one hike to rule them all: Level 3

The Lanikai Pillbox Trail is a quick scramble up the hills above Lanikai and Kailua, and the payoff? Unbelievable views of the bluest ocean crashing around a smattering of rocky islets. My family and I have been hitting this neighborhood trail since our kids were still in diapers. This is one of the most popular Oahu family hikes (for good reason) and it tends to get crowded, but evenings are lovely if you want to avoid (most) crowds.

Maunawili Falls trail, Waimanalo: Level 3-4 (access changed)

The original neighborhood trailhead closed in 2021 and has no confirmed reopening date (if you have enough money and complain enough, you can get a trail shut down). The falls are still reachable via the Maunawili Demonstration Trail from the Pali Highway hairpin turn, but the route is now 6 miles round trip with serious elevation gain. Long-term parking isn’t permitted at the hairpin turn so plan to be dropped off. Hopefully, it reopens soon but in the meantime you can hike a 2-hour out and back stretch of the Maunawili Demonstration trail (that’s how long you can park in the lot off the Pali Highway).

Makapuu lighthouse + tidepools, Makapuu: Level 2-3

The hike to Makapuu lighthouse is an entirely paved, stroller-friendly uphill ascent that rewards you with views of the windward coast and whales in the winter. There’s a trickier side trail from the whale viewing areas that drops steeply down the sharp lava coast to tidepools below. When the seas are calm you can explore the flats and float in the oversized tidepools. More often than not the surf is rough on this coast, so stay back and observe before trying the pools and avoid them during rough weather.

Lulumahu Falls Hike: Level 2

Lulumahu Falls is a 1.7-mile hike through bamboo forest to a 50-foot waterfall, and one of the few legal waterfall hikes on Oahu. You need a $2.50 state permit booked at trails.ehawaii.gov before you go. Expect mud, stream crossings, and pink ribbons to follow when the trail gets unclear. Worth every bit of it.

Likeke Falls Trail, Kaneohe: Level 2

The Likeke Falls trail is another favorite. When the kids were little this was a regular family hike because it’s so short and the falls are fun to play in. Access is through a private parking lot at Ko’olau Ballrooms, which charges a $15 parking fee with the gate open 8am-4pm. Avoid parking along the narrow road outside the gates, which is prone to car break-ins. I say this from personal experience.

Kawainui Marsh trail, Kailua: Level 1

Kawainui marsh trail is popular with residents who you will find walking, jogging, or biking along the scenic route. If you’re staying in Kailua it’s worth a visit for a morning or evening stroll. You can even find some native waterbirds foraging in the marsh. Avoid during the middle of the day when its just too hot.

Preparing for your Hawaii family hike

Preparing for Oahu family hikes requires a bit of planning to ensure everyone’s safety and enjoyment. Here are some steps to help you prepare.

Pack essential hiking supplies

• Reef-safe Sunscreen. Many of Hawaii’s hikes are along exposed ridge trails. Hawaii banned several common sunscreen chemicals in 2021 for good reason.
• Rain protection. Rain can surprise you on the sunniest day. I bring a lightweight drybag to keep valuables and camera gear safe. A long-sleeved shirt and quick-dry clothing is usually enough to keep you comfortable if you get caught in a rainstorm, but layers or a light rain jacket will help in the winter and/or on long hikes.
• Shoes with grip. You can leave the clunky hiking boots behind. Most important for slippery Hawaiian trails is shoes with flexibility and grip.
• Alltrails.com. An excellent hiking app to help you navigate and prepare. You can also learn about current trail conditions and any closures, permits, or fees.
• Geocaching app. Speaking from personal experience, kids can get whiny on hikes. Our fail-proof anti-whine strategy is to hike with friends or, when that’s not possible, search for geocaches along the hike. Don’t forget to brink some trinkets to swap out.
• Water and snacks. Even short hikes can take longer than anticipated. Bring more water than you think you will need.
• Basic First aid kit. You can pick one up at Target or Long’s if you forgot yours
• Wipes and diapers. Wipes and diapers. I remember all too well the time my toddler had a major blowout midway through a 3-mile hike and I’d forgotten diapers, wipes, and a change of clothes.

Can you bring your dog on these hikes?

All of these trails welcome leashed dogs, Maunawili, Makapuu, Lulumahu, Likeke, and Kawainui Marsh and Lanikai all allow them. Crouching Lion doesn’t, but it’s so steep that’s you wouldn’t want to bring your dog anyway.

Can you swim in Hawaii’s freshwater pools?

If you stumble upon a freshwater pool, waterfall, or stream in Hawaii you’ll usually find people playing in the cool water. However it’s not without risk. Leptospirosis is a bacterial disease present in freshwater puddles, ponds, and streams, passed through open cuts or soft tissues. Decide where your comfort level is, but don’t go in with open cuts, avoid putting your head under water, and definitely don’t drink it.

After your Oahu hike – Windward family activities

Local Eateries

Fill your post-hike bellies with tasty local eats and then head back out for more.

• Waiahole Poi Factory. True Hawaiian food that you must experience. Excellent after a big hike and don’t skip dessert.
• Kahuku Superette. This unassuming convenience store serves up some of the tastiest poke on the island. Grab some poke bowls and head to the nearest beach for an instant picnic.
• Over Easy. One breakfast options for the early risers. Local, fresh and super tasty!
• Kalapawai Market. A friendly place to grab anything from a morning coffee to a deli sandwich, pizza, or a full dinner.

Favorite family beaches on the windward side

The windward side of the island is lined with protected bays making ocean conditions calmer and more family-friendly. Try out some of our family’s favorites below:

• Lanikai Beach. A great day starts with a sunrise hike to the Lanikai pillboxes followed by a swim in the cool blue below and then Over Easy for a well-deserved brunch.
• Kahana Bay Beach. A rustic, mellow beach with ample shade and few people.
• Kaiona Beach. Something a little different. Sea walls and shallow water make for perfect baby and toddler pools. A great spot to splash in the shallows or float and relax.

4 must do family activities in windward Oahu (that aren’t hikes or the beach)

1. Kualoa Ranch. Maybe the most majestic place on the entire island. We have done every tour as a family (ebikes are my absolute favorite tour followed by the ATV adventure) and jump at any chance we get to visit the ranch. This includes a painful half marathon we slogged through a few years ago.
2. Hoomaluhia Botanical garden. We used to live in Kaneohe minutes away and visited constantly, which tells you everything. 400 acres of tropical plants tucked against the Koolau mountains, free to enter, and genuinely beautiful even if you just drive to the end of the road and back. Kids can feed the ducks at the lake. There’s something for everyone, including the adults who just want to sit somewhere green and quiet for a while.
3. Kaneohe Sandbar. Sort of a beach, but more like an island in the middle of Kaneohe Bay. The views are unparalleled and it’s a great spot to snorkel with turtles, eagle rays, and colorful fish. If you can find a way out there, it’s worth the effort!
4. Byodo-In temple. A beautiful temple tucked back against the sheer Koolau mountains. A peaceful place to wander and feed the giant koi fish.

For the Family Who Hikes

Families who’ll do a sunrise pillbox scramble or bushwhack through bamboo to a waterfall are usually the same families who show up fully for a fun photo session, not a rushed five minutes in matching outfits but playing, exploring and connecting. If that sounds like your crew, a Lanikai sunrise session captures that same golden-hour energy as the pillbox hike, and a windward morning session leans into exactly this kind of wild, exploring feel. And if it looks like something your family would be into, here’s where to start.

Oahu Hike FAQs