With the fascinating history and some of the best hiking in the world, Hawaii is home to a variety of hiking trails that will also teach us lessons in history and culture. From old military bunkers to ancient Hawaiian fishing villages, these 13 hiking trails found throughout the Hawaiian Islands will lead hikers on an unforgettable journey back in time.
1. Pu’u Loa Petroglyphs Trail, Hawaii Island
Found off the breathtaking Chain of Craters road within Hawaii Volcanoes National Park, this petroglyph site is both gorgeous and culturally significant. More than 23,000 petroglyph images can be found in this expansive field, and you will see many of them along the 1.5-mile (round trip) boardwalk trail.
2. Diamond Head State Monument, Oahu
This iconic Hawaiian hike is perhaps the state’s most popular destination, known for its sweeping views of Honolulu. But not everyone knows that the crater was once home to Fort Ruger, the first United States Military reservation in Hawaii. At one point, hikers will find themselves ascending a spiral staircase inside a coastal artillery observation platform built in 1908. Today, only the Hawaii State Civil Defense and a National Guard facility remain in the crater.
3. Lapakahi Village Interpretive Trail, Hawaii Island
Found within the rugged 262-acre oceanfront park is this easy one-mile loop trail through the partially restored remains of an ancient coastal fishing settlement with a variety of historic structures to check out throughout the carefully-placed footpath.
4. Iao Valley State Park, Maui
In the late 15th century, Maui’s ruler, Kaka’e, designated Iao Valley as an Ali’i burial ground, and in 1790 Kamehameha the Great defeated Kalanikupule and the Maui army during his quest to unify the islands during the Battle of Keaniwai. With a variety of hiking trails leading through the park, you’re sure to find one that suits your skillset.
5. Aiea Loop Trail, Oahu
Approximately halfway through this relatively easy 4.8-mile loop trail in Aiea, the wreckage of a B-24J bomber lies in a valley not far from the trail. The plane crashed here in May 1944 and is often considered to be one of Hawaii’s most well-known crash sites. While the wreckage is hard to spot, it makes for a fun game about halfway through your hike.
6. Ala Kahakai Trail, Hawaii Island
Traversing nearly 175 miles of pristine coastline on Hawaii Island is the Ala Kahakai Trail, established to access the traditional Hawaiian culture and natural resources. The section of trail between Pu'ukohola Heiau National Historic Site and Anaeho'omalu Bay is the most popularly-traveled.
7. Nualolo Cliff Trail, Kauai
A small beach and untouched valley surrounded by towering cliffs, Nualolo Kai is not only home to a large barrier reef, but also to one of the most extensive and well-preserved archaeological sites in all of Hawaii. Nualolo Kai is the site of an ancient Hawaiian fishing village, as well as an extensive Heiau (Hawaiian temple). While you can only visit the valley floor via boat, you can catch a glimpse of this historic site from the Nualolo Cliff Trail.
8. Lanikai Pillboxes, Oahu
This short one-mile hike not only provides stunning views of Windward Oahu — but a glimpse into World War II history as well. During the 1940s, the structures were equipped with telescopes, and soldiers would keep watch for enemy ships and send all relevant information back to Kaneohe Bay Naval Air Station. The pillboxes are now home to a variety of bugs — and a great deal of graffiti.
9. Kilauea Iki, Hawaii Island
This four-mile loop trail, which is the remains of a massive 1959 eruption, is wildly popular among Volcanoes National Park visitors. The trail — which takes hikers through lush rainforests, near active steam and sulfur vents, and across a solidified lava lake — was voted as the Big Island’s favorite scenic hiking trail by Hawaii Magazine. Though this trail doesn’t lead to man-made history, it is perhaps Hawaii’s most significant trail showcasing the islands’ geological history.
10. Pearl Harbor Historic Trail, Oahu
December 7, 1941: A day that will live on in infamy, the Japanese airstrike against the Hawaii naval base killed 2,400 service members and civilians, and injured another 1,200. All eight United States Navy battleships were damaged, and the attack is considered the event that triggered America’s involvement in WWII. Today, a paved trail meanders around the harbor and is the perfect spot for an afternoon stroll full of history. The entire trail is proposed to run 18.6 miles from Halawa Landing to Nanakuli, linking neighborhoods, historic sites, and recreational areas.
11. Captain Cook Memorial, Hawaii Island
On January 17, 1779, Captain James Cook, of Great Britain, sailed into Kealakekua Bay. The native Hawaiian welcomed the Captain and his crew with open arms, believing them to be returning gods. A massive feast was held in their honor, however, a month later, upon realizing that the Captain and his crew were mere mortals, Cook was killed in a conflict. Approximately 99 years later, a 27-foot white obelisk was erected to honor the famous seafarer who first set foot on Kauai a year earlier. It is on the northern tip of the bay that you will find the iconic Captain Cook Monument. The 3.7-mile Ka'Awaloa Trail is one of only a few ways to actually visit the Captain Cook Monument. While you could opt for an easy boat tour or kayaking excursion, this trail will not only lead you to your destination but is quite picturesque as well.
12. Kalaupapa Leper Colony, Molokai
In order to prevent the transmission of leprosy, the Kingdom of Hawaii passed a law in 1965 to send leprosy patients to an isolation settlement on Molokai. At its peak occupation in 1890, approximately 1,100 individuals who suffered from leprosy lived in the colony. Operations seized in 1969, and in 1980, the Kalaupapa National Historical Park was established in order to preserve the culture and physical settings of this former leper colony. While most people choose to take a mule ride to visit Kalaupapa, hiking tours are also available.
13. Haiku Stairs, Oahu
Though this hike is extremely difficult, illegal, and dangerous, it is hard to deny the incredible view. We clearly don’t endorse this hike but it wouldn’t be a list of historic Hawaii hikes without at least mentioning the most famous — after all, the stairs were built to access the Haiku Radio Station, a top-secret facility that was used in order to transmit radio signals to United States Navy ships in operation throughout the Pacific Ocean.