When it comes to hiking, Maui and the Big Island famously have volcanoes to scale, while Kaua‘i has the sheer sea cliffs of the Na Pali Coast. But O‘ahu has equally exhilarating, lesser-known footpaths that let you glimpse Hawaii’s traditional culture and history. Circle the ruins of heiau (temples), climb to the point where souls leap into the afterlife or walk atop the cliffs where ancient warriors battled. Military history fans can hike past 20th-century bunkers and forts or view plane wrecks in the hills above Pearl Harbor. Whichever trail you pick, the Pacific Ocean panoramas will be postcard-perfect.

Diamond Head

A cinematic backdrop to Waikiki Beach, this extinct volcanic landmark requires a hike of less than a mile to reach its summit. From the top of Diamond Head, 360-degree views of the ocean and verdant mountains might knock you off your feet, if strong winds haven’t toppled you first. The trail itself was built in the early 1900s by the US military, which once had observation stations atop the crater rim. Today, the largely unpaved trail passes through concrete tunnels and by leftover military installations, now preserved inside a state park. Wondering about the name? It was given by British sailors who mistook the sparkling of common calcite for more precious gems.

Maunawili Trail network

As you drive from Honolulu over the Pali Highway, one of the most scenic drives in the Hawaiian Islands, pull over at the Nu‘uanu Pali Lookout. It was here, in 1795, that the forces of King Kalanikupule were overwhelmed by the forces of Kamehameha the Great and hundreds of O’ahu warriors were pushed over the cliffs to their death. After snapping a few photos and hanging on to your hat (it’s windy and often chilly!), start walking down the Maunawili Trail, which winds in and out of lush valleys and past waterfalls. The trail extends for 10 miles below the jagged Ko‘olau Range. Most people hike only partway, making a side trip to lacy Maunawili Falls, before returning the way they came to the lookout parking lot.

Lanikai Pillboxes hike

A Windward Coast outing that locals like to keep to themselves, this steep, often muddy trail scrambles to the top of Ka‘iwa Ridge above ritzy Lanikai Beach. The main motivation for making this 2.5-mile round-trip climb is for the boundless ocean views that encompass peaked offshore islands, which paddlers can kayak to from Kailua Beach. But for anyone curious about O‘ahu’s WWII history, it’s the hilltop ‘pillboxes’ (concrete bunkers) along the way that may be most fascinating.

Ka‘ena Point State Park

To really feel the mana (spiritual power) of Hawaiian traditions, as well as the raw power of the sea, drive north along the Wai‘anae Coast to Ka‘ena Point State Park. To get to the point, it’s an easy, level hike of 2.5 miles each way along an abandoned railway track, which used to transport weekenders from Honolulu until just after WWII. Expect to get splashed by the rollicking surf during this walk and bring plenty of water and sunscreen. If you’re lucky, you’ll spot a rare and endangered Hawaiian monk seal hauled out on the rocks or on sandy pocket beaches. From Ka‘ena Point, at the far northwestern tip of the island, the ocean vistas are wildly dramatic. Hawaiian legends say that wandering souls who weren’t met by their ‘aumakua (guardian spirit animal) here would leap into the afterlife, never to return.

Kea‘iwa Heiau State Recreation Area

In the hills of ‘Aiea, west of Honolulu, this state park gives athletic hikers a peek at both ancient Hawaiian culture and modern military history. Near the park’s entrance, you can walk around the lava-rock walls of a centuries-old Hawaiian medicinal temple, still used by lapa‘au (traditional healers) and kahuna (teachers) today. Past the park’s shady picnic area, head off on the almost five-mile loop trail that has sky-high views of the mountains and Pearl Harbor down below. On the east ridge, keep your eyes open for the wreckage of a WWII-era plane.

Sara Benson is a travel writer, digital media creator, all-seasons outdoor enthusiast and former national park ranger. When she's not roaming around Asia, the Pacific and the Americas, she makes her home in coastal California. Follow her on Twitter @indie_traveler.

This article was first published in May 2012 and was refreshed in August 2012

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