Pioneer Inn was constructed at the dawn of the 20th century, in which the United States had started to emerge as a global superpower.

One of the nine contributing buildings that constitute the Lahaina Historic District, the Pioneer Inn has been among Maui’s most prestigious destinations since the early 20th century. Originally built in 1901 by George Alan Freeland, the Pioneer Inn debuted as a first-class destination for travelers passing through the island. The Pioneer Inn was also the first lodging to ever open in the community of Lahaina. When Freeland constructed the building, he used Hawaiian Plantation-style architecture as the source of his inspiration. This was done so those visiting Maui could experience the island’s rich historical past. Freeland even added a movie theater that featured a massive organ, which one of his children regularly played for guests.

During the 1980s, Howard Lennon of Dallas, Texas, managed to acquire the lease to the Pioneer Inn. He then immediately began an expansive series of renovations that both modernized the inn, and preserved its historical integrity. Lennon’s family continued to operate the location over the next several decades, even as the Pioneer Inn joined the Best Western Hotels & Resorts in 1997. Today, the Pioneer Inn remains one of Maui’s most outstanding vacation getaways.