HALEAKALA TRAIL’S RICH CULTURAL PAST
Below is a brief summary of some of the vast evidence and documentation of the cultural history of the Haleakala Trail, including a chronology of significant events. In general, the cultural significance of Haleakala –including the trails used to reach Haleakala—has been well documented by a number of archaeological and cultural studies. One such study summarizes Haleakala’s cultural significance as follows:
The cultural significance of Haleakala—as a place where ceremonial observances were undertaken, the gods communicated with, and loved ones interred, or even taken for transformation into the ‘aumakua realm—dates from antiquity. This is true of Kalialinui, and the lands of Hamakua, Ko‘olau, Hana, Kipahulu, Kaupo, Kahikinui, Honua‘ula and Kula-Makawao regions, where the ala hele [trails] allowed people access to sacred and storied landscapes, as well as access to natural resources only found on the mountain lands. 
Historically, one of the main pathways taken into Haleakala Crater was a permanent overland route from Kaupo, through Haleakala Crater, and down to Makawao/Olinda. The Haleakala Trail (shown in red below ) was part of this overland route (shown in blue below). The other portions of this route were the “Halemau [Halemau’u] Trail that traversed the Crater and the “Kaupo Trail” that descended down Kaupo Gap.
The portion of the overland route identified as the “Haleakala Trail” crossed Crown lands, as depicted in this Hawaiian Government Survey map from 1885  (Crown lands are depicted in yellow; Government lands are depicted in green)
Excerpt from 1885 Hawaiian Government Survey Map
As explained by Martha Fleming in her 1933 book, Old Trails of Maui (which was based on kama‘aina knowledge of the time), the overland route from Kaupo to Makawao/Olinda was one of the permanent pathways on Maui, and it was said that man could travel it in one day:
Besides the encircling paved trail [the alaloa], there was another permanent pathway on Maui, which led from Kaupo across the bed of the crater of Haleakala and up its eastern exit, known as the Halemau [Halemau‘u] trail. This continued on toward Olinda, and provided a short cut across East Maui. A man by this route might reach Olinda from Kaupo in one day.
Below is a chronology that includes some of the vast documentation and evidence of native Hawaiian use of this historical and cultural overland route, including Haleakala Trail:
- At the Holua cave, which is in Haleakala Crater along the Halemau (Halemau‘u) portion of the trail, a well-known archaeological study dates human activity to as early as 1000 A.D., based on an early radiocarbon date. 
- Around 1500, Kiha-a-pi‘ilani, a Makawao chief who unified Maui, is said to have built not only the alaloa that encircled Maui but also a paved stepping stone road in Haleakala Crater that appears to have paralleled the Halemau’u Trail and then ascended to the fresh water pond, Wai Ale, on the east slope of Haleakala. 
- Around 1791, King Kamehameha I likely travelled up the Haleakala Trail and is said to have camped with his troops near the Halemau‘u pali during his Maui campaign. 
- In 1828, native Hawaiians guided up the missionaries Lorrin Andrews, William Richards, and Jonathan Green up the Haleakala Trail from Makawao to the Summit of Haleakala along a route that was described as “long but of easy ascent.” The missionaries documented evidence of previous travel, specifically ancient rock shelters which they assumed were built by native Hawaiians when they travelled from one side of the island to the other. 
- The missionaries frequently returned to the Summit of Haleakala along the Haleakala Trail. Lorrin Andrews made a number of excursions accompanied by his Hawaiian students from the Lahainaluna Seminary on a trail that was described in 1838 as very narrow and “only good for one horse.” 
In 1850, David Malo, the famous Native Hawaiian historian, led C.J. Lyons (who later worked with the Hawaiian Government Survey on the maps shown above) and Father W.P. Alexander on overland route from Kaupo to Makawao/Olinda through the Crater, on a trip “never before undertaken by white men”:
It is an interesting reminiscence of mine that in 1850, Father [W. P.] Alexander, David Malo and myself were a party to make a trip, never before undertaken by white men, from Kaupo, Maui, through the crater of Haleakala to Makawao. Malo was an old man, and it devolved upon me to lead his horse for him as on foot by winding ways we climbed the, for animals, almost impassable steep out of the crater. 
- During his reign from 1855 to 1863, King Kamehameha IV (Alexander Iolani Liholiho) visited Haleakala, almost certainly traveling by way of the Haleakala Trail. The royal excursion was recounted by a friend of the King in the Thrum’s Annual for 1906 as follows:
In my recollection Kamehameha IV was the most of a gentleman in his manner of the five kings I was favored to be acquainted with. He was so from boyhood. On one occasion I was permitted to be a guest with him and the queen and their party on an excursion to Haleakala. The king was the life of the party, very carefully looking after the comfort of the ladies particularly. He roasted the steaks on a long stick for them over the fire for supper, and saw to their sleeping quarters for the night, under the stars. 
- From 1869 to 1885, W.D. Alexander, with the Hawaiian Government Survey, documented the Haleakala Trail on a number of government maps (including those shown above).
- In 1889, the Kingdom of Hawai‘i improved the Haleakala Trail in a significant public works project. In 1905, the Territory of Hawai’i again improved the Haleakala Trail in another significant public works project with the increase in tourism to Haleakala. The 1905 public works project added switchbacks and guideposts at each fifth of a mile that were painted white with black lettering. The remnants of these guideposts still remain today.
- In 1921, Thomas Maunupau, a native of Kaupo who accompanied Kenneth P. Emory in his famous archaeological survey of Haleakala, described the Halemau‘u trail travelling through Haleakala Crater as follows:
Beside the old road made by the ancients [the paved royal road of Kiha-a-pi‘ilani], there was a latter one, Halamauu [Halemau‘u] road. This road went up the other side of the mountain toward Olinda. By following up this road the first noted place we came to was Keahuakaholo [in the center of Haleakala Crater]. There were rock piles everywhere standing here and there like people. This place had more stone piles in one place than at any other place on the mountain. We left Keahuokaholo and came to [Na] Piko Haua. This is the place where the umbilical cords of babies of old and the babies of this later time are deposited … Close to a ridge on the mountain is a place called Hoolua [Holua cave]. In other words it means that this is a place of the wind and from here the Hoolua breezes blow far and wide. 
- The kama‘aina testimony of Jacob R. Mau, who worked for the Department of Land and Natural Resources in the 1960s, also recounts how his elders told him about the overland route from Kaupo to Makawao:
He learned from his elders that:
At times in the past, they traveled the old trails from Kaupo to Paliku, Halemau (Halemau‘u), and out to Makawao. It was a difficult trip, and in the early ranching days, one that was made until the ranch resorted to shipping the pipi (cattle) to Nu‘u, or driving the cattle around the mountain instead… 
 Kepa and Onaona Maly, Cultural-Historical Study of East Maui—The Uplands of Kalialinui, and the Lands that Lie Below, Island of Maui (2006), pp. 99-100.
 Maui, Hawaiian Islands. 1885, brought up to date in 1903 by John M. Donn. Hawaiian Government Survey. W.D. Alexander, Surveyor General; Primary Triangulation by W.D. Alexander and S.E. Bishop; Boundaries and topography by W.D. Alexander, C.J. Lyons, M. D.. Monsarrat, F.S. Dodge, S.E. Bishop, E.D. Baldwin, and W.R. Lawrence; Map by F.S. Dodge. Scale 1:60000. (Collections of the Hawai‘i State Survey Division).
 Maui, Hawaiian Islands. 1885. Hawaiian Government Survey; W.D. Alexander, Surveyor General; Primary Triangulation by W.D. Alexander and S.E. Bishop; Boundaries and topography by W.D. Alexander, C.J. Lyons, M. D.. Monsarrat, F.S. Dodge, S.E. Bishop, E.D. Baldwin, and W.R. Lawrence; Map by F.S. Dodge. Scale 1:60000. (Geography and Map Division, Library of Congress). RM No. 1268.
 Martha Foss Fleming, Old Trails of Maui (1933), p. 86.
 Lloyd J. Soehren, An Archaeological Survey of Portions of East Maui (1963), pp. 111-116.
 Kenneth P. Emory, An Archaeological Survey of Haleakala (1998), p. 249.
 Fleming, op. cit. p. 86.
 Anon., “Sandwich Islands—Tour around Maui” in The Missionary Herald, Vol. XXV, No. 8 (August 1829), pp. 246-251.
 The 1838 account of the Summit expedition is from a Hawaiian language newspaper, Ke Kumu Hawaii (June 20, 1838), and is republished and translated by Maly, op. cit. p.29.
 C.J. Lyons, “David Malo’s Lament for Kaahumanu” in The Friend, Vol. 53, No. 8 (August 1895), p.1.
 “The Kamehameha IV. – Neilson Tragedy,” Hawaiian Almanac and Annual for 1906, p. 90.
 Maunupau, Thomas K., A Visit to Kaupo, Maui (1923), pp. 145-46.
 Maly, op. cit. p. 158.