Historic boardwalks and buildings of Old Kōloa Town

Walking Tour of Old Kōloa Town

Step into the past and discover the stories behind the buildings

Written by a Local Kauaʻi Expert

A Guided Walk Through Old Kōloa Town Today

The best way to experience Old Kōloa Town is to walk its streets. As you stroll under the shade of the broad-leafed monkeypod trees, I invite you to see the town through my eyes. Look past the modern storefronts and listen to the stories the buildings have to tell.

The Architectural Time Capsule: How to Read the Buildings

The buildings of Old Kōloa Town are a masterclass in plantation-era architecture, a style born of practicality and a touch of frontier bravado. Notice the characteristic false fronts on many of the one-story buildings. These were designed to make the structures look taller and more imposing from the street. The wide, covered boardwalks and verandas, or lanais, weren't just for show—they provided essential shade from the tropical sun and a place for neighbors to stop and "talk story." Most are built with simple wood-frame construction and topped with corrugated tin roofs, which create a soothing drumbeat during a passing rain shower. Each building is a chapter in the town's history, and many have plaques detailing their original purpose.

Let's take a walk. As we stroll through the Waikomo Shops courtyard, look up at that two-story building, the only one of its kind left from the old days. Each storefront has a story waiting to be discovered.

The Historic Buildings

As we stroll through the Waikomo Shops courtyard, look up at that two-story building, the only one of its kind left from the old days. That's the Okumura Building (Building 15), built in 1905. The Okumura family, who lived upstairs, ran a general store below, catering to workers from the nearby Lāwaʻi pineapple cannery. My grandmother told me stories she heard about Mr. Okumura, how he would personally take orders from families in the work camps and deliver them later, often extending credit to those who were struggling. It's said that years after the store closed in the 1950s, every single customer had loyally paid back their debt. That's the kind of community this was.

🌳 Yamamoto Store & Monkeypod Tree

Now home to Crazy Shirts, this was once the Yamamoto Store (Building 8), first built in 1898—the oldest commercial building in town. In the 1920s, Howard Yamamoto planted the giant monkeypod tree that now shades the courtyard. The store became the town's unofficial gathering spot.

🏨 Kōloa Hotel (Building 9)

Thought to be Kauaʻi's second hotel, it provided lodging for the traveling salesmen, or "drummers," who came to the island on business. Next door to the Yamamoto Store, it was a central part of the town's commercial life.

🍞 Chang Fook Building (Building 2)

Famous across the island for its bakery, started in the 1930s. The aroma of fresh-baked goods would fill the street, drawing customers from all over the South Shore.

🏥 Kawamoto Building (Building 6)

Once housed the Kōloa Dispensary, the only medical facility for the entire plantation community from 1900 to the 1930s. This building served as the lifeline for workers and their families.

And tucked away, there was even a separate building for the Kōloa Hotel O-Furo (Building 11), a Japanese-style communal bathhouse with a charcoal-heated tub, a testament to the cultural traditions the immigrants brought with them.

Every building has a similar story. As you walk through Old Kōloa Town, take your time. Read the plaques. Sit on the benches under the monkeypod trees. Feel the weight of history in these weathered boards and tin roofs. This is more than preservation—it's a living connection to the past.