How the Pali Highway Came to Be

The Pali Highway: From Rough Trail to Daily Commute

 By Kristen Pedersen

Those of us who live on the windward side of Oahu zip back and forth to Honolulu on the Pali Highway without a moment’s thought. The 11 miles of highway that we now know so well is actually the third roadway constructed across and through the Koolaus and Nuuanu Valley. It connects Kailua and Kaneohe with Vineyard Boulevard in downtown Honolulu. Not so well known is that getting across this expanse wasn’t always so easy.

Before the highway or road existed, you had several options: take a canoe around the island; trek through the back of Kalihi Valley; or hike the most direct (and dangerous) route on a trail over the Pali cliffs.

In the early 1800’s, the cliffs trail was the main route farmers in the Kailua area used to bring produce to sell in the city and transport necessary goods back to the windward side. According to Kailua archaeologist Paul Brennan in his book KAILUA, the route was a scary series of “ropes and ladders where travelers had to climb straight up or down. Still, they trekked the trail every day, taking poi, fruits, sweet potato and pigs to residents of the city.”

In 1845, the narrow trail was widened to six feet and paved with large stones, allowing easier passage for horses and carts. This first Pali Road was a critically important improvement to the lives of farmers and their families, but as late as 1877, even with continued enhancements, was still not considered a safe passage.

In 1896, the legislature authorized the use of dynamite to widen the road for paving. A young engineer, Johnny Wilson, headed up the much-needed project. (Interesting side note: Wilson, a civil engineer and co-founder of the Democratic Party of Hawai‘i, would later be elected mayor of Honolulu.) Another widening and paving project just after 1900 allowed for automobiles and trucks to travel the road. By 1931, more than 2000 cars were navigating the 22 hairpin turns of the Old Pali Highway every day.