Hana Highway History: Uncovering the Stories Behind Maui’s Legendary Road

That image — bodies suspended over rainforest ravines, dynamite in hand — is a long way from the sunscreen-and-playlist version of the Road to Hāna most visitors come with. Today, the 64-mile stretch of Highway 360 is known for 620 curves, 59 bridges, black-sand beaches, and banana bread stands. But the road itself is a layered artifact: a 20th-century infrastructure project built atop a 16th-century Hawaiian footpath, pushed through by plantation economics, and later transformed into a tourism corridor by a San Francisco entrepreneur. This article traces the forces — ancient and modern, Hawaiian and haole, sacred and commercial — that shaped the Hāna Highway, and asks what the road reveals about Maui’s contested history of land, labor, and access.

Quick-Reference Table: Four Eras of the Hāna Highway

Each era left its mark not just on the pavement but on the communities who live along it. The road was never neutral — it was always about who got to move, and why.

The Ala-loa: Footpaths of the 16th Century

Long before any automobile crossed East Maui, a network of footpaths known as the ala loa — “long road” — connected the villages scattered along the coast. In the 16th century, Maui’s ruling sovereign Piʻilani began constructing a lava-stone path to link communities across the island. His son later extended the trail into the Hāna district, creating a route that would, centuries later, guide the highway engineers. According to the National Park Service, the Ala-loa spanned roughly 138 miles and was about 4 to 6 feet wide, with vine ropes used to cross streams.

These trails were not merely utilitarian. They followed the contours of the land — past taro loʻi (irrigated terraces), fishing grounds, and heiau (temples) — and were embedded with spiritual and political meaning. The Ala-loa was a statement of a chief’s reach, a way to assert authority over a district as much as a way to move goods. For a deeper look at the role of taro in shaping Hawaiian land use and community life, see the guide to taro farming on IslandHopperGuides.

What remains debated among historians is the exact route of the original Ala-loa. Much of it was destroyed or buried by plantation agriculture and later road construction, and oral traditions from different ahupuaʻa (land divisions) sometimes describe overlapping or contradictory paths. The Hawaiian Trail and Mountain Club has worked to document surviving segments, but no single authoritative map exists.

From Wagon Road to Highway: 1910–1926

The modern road began not as a tourist initiative but as an industrial corridor. In the 1870s, plantation developers built an unpaved wagon road alongside the Hāmākua Ditch, an irrigation project that diverted East Maui’s abundant rainfall to the sugar fields of central Maui. The road served the cane industry first, and everyone else second.

By 1910, the Hawaii Territorial government decided to build a proper highway. The terrain was brutal: dense rainforest, sea cliffs, and deep gulches that required dozens of bridges. Workers — many of them prison laborers from the Oahu Prison, along with Native Hawaiians and immigrant workers from Japan, China, and Portugal — were lowered over the cliffs with ropes to drill and blast rock. The Honolulu Advertiser reported in 1926 that the road cost one worker’s life, though oral accounts from Hāna families suggest the number was higher; the official record is incomplete.

The road officially opened to cars in 1926. George Denison, general manager of the Oahu Railway and Tourist Bureau, told the Honolulu Advertiser at the dedication ceremony: “It’s just one more link in Hawaii’s chain of unexcelled scenic attractions… As the Governor Farrington said at the official ceremonies at Hana Saturday the new road means much to Hana, more to Maui but most to all Hawaii.” The road was added to the National Register of Historic Places in 2001, though only 59 of its original bridges remain, and many have been reinforced or replaced.

Paul Fagan and the Transformation of Hāna

If the territorial government built the road, it was a San Francisco entrepreneur named Paul Fagan who turned it into a destination. In 1929, Fagan married Helene Irwin, daughter of a Hawaii sugar pioneer, and the couple divided their time between California and Hawaii. Fagan purchased 10,000 acres of former sugar land in Hāna and established Hana Ranch. In 1946, he opened the six-room Kauiki Inn, which later expanded into a 70-room resort — the Hana Ranch Hotel.

Fagan was also the owner of the San Francisco Seals of the Pacific Coast League. He brought the team to Hāna for spring training and invited sports writers to cover it, generating mainland press attention that the territorial tourist bureau could not have afforded. “Hana offers the tourist and vacationist the finest facilities for pleasure and enjoyment,” he told the Honolulu Star-Bulletin in 1945. “The natural scenic beauty has all the loveliness for which Hawaii is noted.”

In 1950, Fagan realized another ambition: the opening of Hana Airport, a small airstrip on a field off Hamoa Beach that made it possible for visitors to skip the long drive entirely. After Fagan’s death in 1960, his wife built a 30-foot-tall stone cross memorial — known as Fagan’s Cross — on a ridge above Hāna, accessible by a one-mile hike at 500 feet elevation. The cross remains a popular sunrise viewpoint, though its presence sits uneasily for some residents who see it as a monument to a haole landowner’s legacy rather than a community landmark.

The Road Today: Between Preservation and Pressure

Between 400 and 600 people drive the Hāna Highway on an average day, according to Hawaii News Now. The road is fully paved, and the journey takes 2 to 3 hours without stops — though most visitors stretch it to 8 to 10 hours with stops at Waiʻānapanapa State Park, ʻOheʻo Gulch (the so-called Seven Sacred Pools), and the Keʻanae Peninsula. The phrase “Seven Sacred Pools” was a marketing invention, not a traditional Hawaiian name; the site is known in Hawaiian as ʻOheʻo Gulch, a series of cascades and pools within Haleakalā National Park. Paul Fagan helped popularize the English name through media campaigns in the 1940s.

Waiʻānapanapa State Park, with its black sand beach, sea arches, and blowholes, now requires a timed-entry reservation system — a direct response to overcrowding and parking issues. The reservation system, managed by the Hawaii Department of Land and Natural Resources, has reduced daily visitor numbers but has also created a new problem: visitors who cannot secure a reservation sometimes park illegally along the highway, creating safety hazards on the narrow, winding road.

The road’s popularity has also intensified long-standing tensions between residents and visitors. Hāna residents have repeatedly voiced concerns about disrespectful behavior — visitors trespassing on private property, leaving trash at roadside fruit stands, blocking driveways, and treating the town as a drive-through attraction rather than a living community. The 2021 visitor boom, which followed pandemic lockdowns, prompted a coalition of East Maui residents to call for a temporary moratorium on tour permits. The request was not granted, but it highlighted fractures in the tourism model that the road sustains.

Context & Comparison: Travel Then and Now

The comparison reveals something obvious but worth stating: the road has always been a boundary between worlds. For ancient Hawaiians, the journey was part of a seasonal cycle of movement and exchange. For mid-century drivers, it was an adventure requiring grit. For today’s visitor, it is increasingly a managed experience — timed, ticketed, and curated. None of these modes is inherently better or worse, but each reflects a different relationship to the land.

Questions Readers Ask

How many people died building the Road to Hāna?

The official 1926 Honolulu Advertiser account reported one worker’s death. Oral histories from Hāna families suggest the number was higher, but no comprehensive record survives. The road was built by prison laborers whose deaths were not always officially recorded. This remains an unresolved historical question.

Is the “Seven Sacred Pools” a real Hawaiian name?

No. The name “Seven Sacred Pools” was a 1940s marketing invention promoted by Paul Fagan and taken up by travel writers. The site is called ʻOheʻo Gulch in Hawaiian, and the pools are not seven in number — there are more than 20 cascades and pools along the stream. The National Park Service refers to the area as the Pools of ʻOheʻo.

Why does the road have so many one-lane bridges?

The 59 bridges were built between 1910 and the 1930s, when the road was carved through deep gulches and streambeds. Widening the bridges would require major engineering work and would likely damage the stream ecosystems. Many of the bridges are considered historic structures as part of the road’s National Register listing, which limits modifications.

Can you drive the Road to Hāna without a reservation?

You can drive the road without a reservation, but you cannot stop at Waiʻānapanapa State Park without one. The park requires a timed-entry reservation, and parking is strictly limited. Other stops — like Keʻanae Peninsula, Halfway to Hāna Stand, and Twin Falls (with a $10 parking fee) — do not require advance booking but can be crowded.

The Road as a Record

The Hāna Highway is not just a route to waterfalls and black sand. It is a physical record of Maui’s layered history — a 16th-century footpath that became a plantation supply line, then a territorial highway, then a tourism corridor. Each layer is still visible if you look: the narrow bridges built for horse-drawn wagons, the cliff faces still scarred by dynamite, the taro patches that predate the pavement, and the reservation system that tries — with mixed success — to protect the community from its own popularity. The road reveals something uncomfortable about the relationship between mobility and displacement: the same infrastructure that connects outsiders to a place can also disconnect the people who live there from their own land. For a deeper look at how Hawaiian communities have maintained their cultural practices through similar pressures, the guide to lei making and the art of giving and receiving aloha offers a relevant perspective.

Sources and further reading

National Geographic. “The Road to Hāna.” 2024. 🔗

SFGate. “The Road to Hana and its San Francisco origins.” 2023. 🔗

Hawaii Activities. “The History of the Road to Hana.” 2024. 🔗

Stardust Hawaii. “From Past to Present: The Evolution of Hawaii’s Road to Hana.” 2025. 🔗

Related reading on IslandHopperGuides

The Spirit of Aloha in Native Hawaiian Chants — explores the oral traditions that have carried Hawaiian history and identity across generations, including the chants that reference the Ala-loa and the landscapes of East Maui.

Luau Decoded: A Deep Dive into the History, Rituals, and Authentic Flavors — provides context for the food traditions travelers encounter at roadside stands along the Hāna Highway, from banana bread to huli huli chicken.