From Hawaii’s first residents and the first Europeans visiting the islands in 1778 to the establishment of the Kingdom of Hawaii in 1795 and Hawaii’s admittance to the United States of America in 1959, the Hawaiian Islands are steeped in history, heritage, and culture. And nowhere will you find more history than in the Aloha State’s oldest towns. Our beautiful islands have undergone monumental change throughout history, and these old-fashioned towns only get better with age. From vibrant shops set up in plantation-style storefronts to historic landmarks and everything in between, there is certainly something special about these 9 old-fashioned towns.
The largest town on the small island of Molokai, Kaunakakai is full of history. When pineapple and sugar exports were huge in Hawaii, Kaunakakai was a bustling port town. King Kamehameha V’s royal summer residence was once in this ancient canoe landing, and now the Old Western-style storefronts paint the picture of a town stuck in time.
Like much of Hawaii, Hilo was once the site of major sugar production, and because the city never experienced huge tourist draws like other Hawaii locals, it has stayed true to the state’s pre-World War II persona, which vintage storefronts, and plenty of charm.
While Wailuku is home to popular local shops, restaurants, and bakeries that have been around for generations, the town also features emerging boutiques and laid-back cafes and coffee shops. Conveniently located just 10 minutes from Kahului, Wailuku also serves as the gateway to the lush Iao Valley. Wailuku is the perfect blend of old and new, and it’s sure to please.
With the greatest concentration of artists on the island, Hanapepe is known as “Kauai’s Biggest Little Town.” Its historic, plantation-style buildings are now home to charming shops, eateries and a surprising amount of art galleries — and it’s a beautiful place for a weekend retreat.
5. Lanai City
Sitting approximately 1,600 feet above sea level is this small city, settled in the 1920s when sugar cane and pineapple production was king. A collective of pastel-colored, tin-roofed cottages dates to the town’s settlement. Not only was the first sugar mill in Hawaii founded on Lanai in 1802, but the town was once home to James Dole’s pineapple plantation, which employed thousands.
Located in upcountry Maui on the rural northwest slopes of Mount Haleakala is a charming little town worthy of a visit — and a little recognition. With a population of approximately 7,100, Makawao is one of Hawaii’s biggest little towns. The town is famous for its Hawaiian cowboy, or paniolo, history, and is a haven for artists of all kinds.
7. Old Koloa Town
Home to Hawaii’s first ever commercially successful sugarcane plantation, Old Koloa Town is a relic of days gone by. The Koloa Sugar Mill opened in 1935, and by 1898, was producing approximately 225,000 tons of sugar each year. The mill moved in 1912, but production remained strong until 1996.
Located on Hawaii Island’s Hamakua Coast, Honoka’a was once the third largest town in Hawaii but is now home to less than 2,300 residents. Like many towns on this island of Hawaii, Honoka’a grew due to the prolific and profitable sugarcane industry. But the largest sugar company near Honoka’a closed in 1994, resulting in a charming, quiet town that will make you feel a million miles away from it all.
Though Hanalei is located just north of the Princeville resort area, it feels like worlds away from the Hawaiian tourism scene. With a small one-lane bridge leading into town, and an unusual mix of shopping and dining options, the very small town — approximately 0.8 square miles — is full of old world charm. We hope the town retains its charm after the recent flooding that has caused devastation across Kauai’s north shore, but more importantly, we hope Hanalei’s residents are safe.