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Dwarfing the mountain ranges of Oahu in elevation, the West Maui Mountains summits at 5,788 feet on Puu Kukui. The largest valley on the windward side of the mountains, Iao watershed, borders another sizable valley on it's leeward side, Olowalu, by a saddle known as the Iao-Olowalu Pass. The pass was used as an ancient Hawaiian route to crossover the West Maui Mountains, which may have considerably shortened travel between the districts of Lahaina and Wailuku. The pass has particularly been known as the escape route used by the King of Maui when attacked by King Kamehameha during the battle of Kepaniwai in 1790. It was then used by missionaries until the mid 1870's when erosion made it unpassable by most. Other documented records of successful attempts occurred in 1917, 1966 and 1978, however it is possible there are several other more recent undocumented accounts. Note, there have also been several documented attempts of that have failed, which have either resulted in injury and/or death of the attemptee(s). After much discussion and planning by an experienced group of local hikers (Pete Clines, Chase Norton, August Smith, Laredo Muredo, Joshua "Nectar" Nipp, Nate Yuen and myself), we set out traverse the Iao-Olowalu Pass and succeeded safely in May 2012.