My 6 Favorite Hikes on Oʻahu: What to Expect, Difficulty & Practical Tips

Oʻahu packs a huge variety of hiking experiences into one island — from steep railway steps to gentle paved coastal paths and leafy waterfall walks. Here are six favorites, with quick facts (difficulty, length, terrain) and where to go.

1. Koko Head Crater (Koko Crater Railway Trail)

Location: Hawai‘i Kai / Koko Head Park

Difficulty: Hard — very steep, strenuous

Length: ~1.6 miles round-trip (about 1 mile one way depending on start)

Terrain: Very steep railroad-tie steps, rocky near summit, exposed to sun and wind

Koko Head is the classic “stairmaster” — a straight, steep climb up hundreds (commonly cited ~1,048) of old railway ties used during WWII. It’s short but brutal: expect heavy breathing, strong legs, and outstanding sweeping views of Hanauma Bay, the southeastern shoreline, and the crater rim. Go early for cooler temps and fewer people; note that sections can be uneven and there have been closures and safety advisories at times, so check current status before you go.

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2. Kuliʻouʻou Ridge Trail

Location: Windward side (Hawai‘i Kai / near Waimanalo side)

Difficulty: Moderate — steady climb with switchbacks

Length: ~4.5–5 miles round-trip (varies by route)

Terrain: Forested singletrack, roots and rocks, ridge panoramas

Kuliʻouʻou Ridge is a favorite for a longer, scenic ridge hike without technical scrambling. The trail starts shaded and climbs through switchbacks before opening to ridge-line viewpoints over windward Oʻahu. It’s a satisfying workout with enough length to feel like a proper hike but not so steep as to require scrambling. Bring water and expect some muddy patches after rain.

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3. Waimano Falls (Pearl City)

Location: Waimano Valley / Pearl City foothills

Difficulty: Moderate (can be muddy and slippery)

Length: ~2.5–3 miles round-trip (depending on path and approach)

Terrain: Valley trail, stream crossings, uneven/muddy sections, waterfall pool

Waimano Falls is a popular local waterfall hike that takes you up a scenic valley with stream crossings and lush vegetation before you reach the falls. The route can get muddy and slippery, especially after rainfall, and some sections are steep on the return. It’s a great option if you want a waterfall destination without a full-day commitment — bring sturdy shoes and be prepared for wet footing.

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4. Makapuʻu Point Lighthouse Trail (family-friendly)

Location: Southeast coast — Makapuʻu / Waimānalo area

Difficulty: Easy to Moderate (gentle steady incline)

Length: ~2 miles round-trip

Terrain: Paved path, exposed to sun, gentle grades

Makapuʻu is the go-to family-friendly coastal walk: a paved trail with manageable incline and dramatic ocean views. It’s an excellent sunrise or morning hike and offers seasonal whale-watching from the overlook during winter. Parking is available at a small lot near the trailhead; bring sunscreen and water because there’s little shade.

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5. Lanikai Pillbox Hike (Kaʻiwa Ridge Trail)

Location: Lanikai / Kailua (windward side)

Difficulty: Easy–Moderate (short but steep in places)

Length: ~1–1.7 miles round-trip depending on route and how far you explore

Terrain: Narrow dirt/rocky ridge, some steep and crumbly sections, old military pillboxes (concrete bunkers)

Short and iconic, the Lanikai Pillbox (Kaʻiwa Ridge) trail delivers big tropical views for relatively little distance. The trail climbs quickly to a pair of WWII-era concrete pillboxes that make great lookout spots for sunrise or photos of the Mokulua islets and turquoise water. Because the ridge is narrow in spots and parking in the neighborhood is limited, arrive early and be respectful of local residents.

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6. Lulumahu Falls Trail (near Pali / Nuuanu)

Location: Nuuanu / near the Pali lookout (windward side of Nuʻuanu Valley)

Difficulty: Moderate (watch for route splits and muddy sections)

Length: Short — typically ~1–2 miles round-trip depending on route taken

Terrain: Forested valley paths, streamside walking, some uneven/muddy footing, reservoir area near trailhead

Lulumahu Falls is a short, jungle-feeling hike that rewards you with a pleasant waterfall and pool. The trail can be a little confusing at one split (take care not to head onto the longer, more difficult alternate routes), and some sections cross near stream or reservoir structures, so solid footwear is recommended. It’s a peaceful, green escape close to the Pali corridor.