Staying Power


Story by Sarah Ruppenthal

Pioneer Inn
Photo by Ron Dahlquist

Est. 1901

What do Jack London, Frank Sinatra and Katharine Hepburn have in common? Apart from being American icons, all three were once overnight guests at The Pioneer Inn.

Built in 1901, the Pioneer Inn is the oldest hotel on Maui and the longest continuously operating hotel in Hawai‘i. The two story plantation-style establishment overlooks Lahaina Harbor in the Lahaina Historic District. It became affiliated with Best Western Hotels & Resorts in 1997, and in 2016 was inducted into the Historic Hotels of America program as part of the National Trust for Historic Preservation.

Over the decades, many luminaries have stayed or dined there, including Spencer Tracy, Mark Twain, Jerry Lewis, Peter Fonda, Jacqueline Kennedy Onassis and Sun Yat-sen. The Inn was immortalized on screen in the 1961 film The Devil at 4 O’Clock, and also has been featured in episodes of Hawaii Five-0, Baywatch, Hawaiian Eye and Adventures in Paradise. A long history also means lots of tall tales and legends. One of the more popular ones is that a horse — yes, a horse — was once kicked out of the bar for unruly behavior.

Pioneer Inn
Pioneer Inn in the 1920s

There’s also a rumor that the man who built the hotel, a Canadian police officer named George Freeland, initially came to Maui in hot pursuit of a wanted fugitive. Freeland never caught him, apparently, but instead fell in love with the Island and decided to stay. But Freeland wasn’t the only one reluctant to leave: Hotel staff recently discovered that a crab, whom they affectionately named Louie, had been happily residing under the floorboards of the bar. Jim Lennon, coproprietor of the Inn with wife Becky, scooped him up and carried him to the ocean, but Louie came skittering back into the bar just a few hours later.

Step inside, and you’re surrounded by turn-of-the century architectural details and the decor whispers tales of sea and sailing. The Inn also has plenty of quirky charm, including Alex, the wisecracking house parrot, and a life-size wooden sculpture of a sea captain at the front entrance.

But perhaps more remarkable than any fable or Hollywood fame is the fact that the Pioneer Inn has never closed — not once in its 120-year history. Even during the pandemic, its doors remained open, despite all the rooms being vacant, and the reasons for that were twofold. “First, to retain as much staff as we could justify, and second, to protect and preserve an iconic property in a very public location,” says Becky Lennon. In 1982, Howard Lennon (Jim’s father) acquired the master lease for the Inn and worked diligently to renovate and modernize it without compromising its historic integrity. The Lennons took the reins in 1998 and have since maintained the property, which is a near-constant endeavor, given that the Inn is more than 100 years old.

Regardless of its age, the hotel meets modern day standards, and all 40 rooms have amenities such as complimentary WiFi, flat-screen televisions, coffee makers and mini fridges. And in 2020, the Lennons brought in Lee Anne Wong as executive chef of Papa‘aina, formerly the Pioneer Inn Grill and Bar (and before that the Old Whalers Grog Shop). If her name sounds familiar, here’s a hint: Wong was a fan favorite on Bravo’s Top Chef series and on the Food Network’s Iron Chef America. (Wong is also featured in this issue’s “Chef’s Kitchen”.)

A lot has changed in the last 120 years, but one thing remains constant at the Pioneer Inn: “We will always preserve the history and hospitality of plantation-era Hawai‘i while updating with modern amenities for today’s travelers,” say the Lennons.

The Best Western Pioneer Inn, 658 Wharf St., Lahaina | 808.661.3636 | | IG/FB @pioneerinnmaui



  1. We were sorry to see the Old Whaler’s Grog Shop go away. That was a REAL bar, nothing frou-frou about it, and the naked lady over the bar made it even cooler


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