With its white first- and second-story lanai encircling the building and set off by a field of plantation-green walls and a red corrugated metal hipped roof, the Pioneer Inn has anchored the harbor front of Lahaina since 1901 when it opened under the management of George Freeland. The original makai side of the building was substantially expanded in 1964, resulting in a landscaped interior courtyard. The addition contains approximately twenty shops and eateries on the first floor.
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