Enjoy time in the outdoors with your ohana! (And check my CafePress site for buttons for your little peakbaggers! Not all trails have buttons yet, so feel free to contribute your artwork for any missing buttons and I’ll make one!)

Judd Memorial Trail, Nuuanu Great 1 mile hike with only 250′ elevation gain, just off Nuuanu Pali Dr. This shady loop hike includes a large pool and stream. A side trip just up the road from the trailhead includes a bamboo forest walk to King Kamehameha III’s summer palace.
Pu’u Ohia, Tantalus Great 1.5 mile walk through a bamboo forest on a gentle grade. Mt. Tantalus summit.
Pu’u Ualaka’a This 1.7 mile shaded forest loop starts out with a great overlook where you can see Honolulu, Waikiki and Diamond Head. Then head into the forest and smell eucalyptus! Shaded, gentle grade.
Likeke Falls, Kaneohe Wonderful, shady, 1.7 mile (roundtrip) hike up a gradual grade to a waterfall and a view of Kaneohe Bay.
Pu’u Pia, Manoa Valley Great 2.4 mile (roundtrip) hike for kids! Shady 90% of the way, good lunch spot, no treachery! Beautiful views of Manoa Valley from the summit. Also a great vantage point to see Honolulu and the ocean beyond. Highly recommended.
Bellows Loop Trail, Waimanalo - Great hike for families! This 2.8 mile trail is stroller/hiker/biker/jogger friendly with good shade for about half of the trail. No elevation gain. Playground and snack bar at the Registration building. This is a military base, however, so it is closed to the general public.
Ho’omaluhia Botanical Gardens, Kaneohe - lots of shady trails among collections of plants from other Pacific islands.
Friendship Garden, Kaneohe - this is a great hike to do with a little one, either in a carrier or hiking by your side. The trail is comprised of two small loops, about 1 mile total distance. It is shaded and there is a little covered picnic spot and a garden, along with great views of K-bay. Map, links and directions provided at the link above.
Makapuu Lighthouse, Hawaii Kai - paved trail 1.5 mi one way up a gradual incline. Stroller-friendly. Good for whale watching in the winter months. Totally exposed, windy, potentially hot.
Manoa Falls, University area - This shady hike to a waterfall is about 2 miles roundtrip with very moderate elevation gain. This is doable for kids but caution needs to be exerted near streams and over roots, boulders, etc. as with any hike.
Hau’ula Loop Trail This 2.7 mile shady hike provides 600 ft of elevation gain at the beginning of the lollipop route, some scenic views of the windward beach and lush forests. Great hike for families with kids of all ages.
Waimea Falls, North Shore - This hike is paved, and about 3 miles roundtrip, slight elevation gain. It’s run by the Audobon Society so there is an admission fee. It’s beautiful and easy for families. Stroller-friendly. (Tel. 808/638-9199)
Waihe’e Falls, Kahalu’u This gentle, 3.6 mile (roundtrip) hike takes you to the base of a large waterfall set deep in the Waihe’e Valley. Gravel road the whole way, about 500 ft elevation gain. Good for the whole family if you have avid walkers or pack-riders. Gravel road is stroller-friendly until you get to the steeper sections along the second half of the trail to the falls.
Maunawili Demonstration Trail, Pali Hwy - relatively level hike that hugs the Ko’olau Mountains from the Pali to Waimanalo. Go as far as you want and turn back. Great views offered along the way, and a connector trail to the Maunawili falls (0.7 miles long) can be found 3 mi into the trail from the Pali trailhead.
Aiea Loop Trail - This 5 mi loop trail is great for kids. There is some elevation gain but it’s shady and well-traveled.
Mariner’s Ridge, Hawaii Kai - This hike is a good one for kids. It’s 3 miles roundtrip with 850′ elevation gain to a great view of both the windward and leeward sides of the island. You need to use caution at the summit, but the trail itself is well-suited for kids.
Lanikai Pill Box - This hike is a bit more challenging to do with a child, but possible. It is about 3 miles total length if you do the entire loop, or about 1 mile total if you just head up to the second bunker and back. The footing is slippery at first (ropes are in place now) and the ascent is steep (500′ in 0.25 mi). See full write-up at link above for detailed review and directions to the trail head.
Kuliou’ou Ridge, Hawaii Kai - 5 miles roundtrip with 1800′ elevation gain to sweeping views of the windward side. The first half is shady and has well-graded switchbacks to lessen the impact of the rapid elevation gain. The second half to the summit is exposed, slippery in some areas, and somewhat narrow. No room to play at the summit! I recommend Mariner’s Ridge for kids.

Let me know if you have other suggestions that meet my “choosy mom” criteria!