Scenic view of Hanalei Beach in Kauai, Hawaii. Image credit jerzy via AdobeStock.

9 Oldest Founded Towns To Visit In Hawaii

Be immersed in the rich history and captivating charm of Hawaii's oldest towns while embarking on a journey that unveils the island's ancient past. From the vibrant streets of Lahaina on Maui, to the colonial architecture of Paia on Kauai, these enchanting destinations offer a glimpse into Hawaii's cultural heritage and diverse communities. Walk along weathered wooden storefronts, explore historic landmarks, and savor the flavors of traditional cuisine. Whether it is the remnants of sugarcane plantations in Waimea or the royal palaces of Hilo, each town holds stories of a bygone era offering a captivating and unforgettable experience for every visitor.

Lahaina

View of the Lahaina Marina and the West Maui Mountains
Lahaina marina. Image credit stevengaertner via AdobeStock.

Lahaina, located on the western coast of Maui, holds a rich and captivating history. In the early 19th century, Lahaina became a bustling whaling port, drawing hundreds of ships worldwide. Today, Lahaina preserves its rich heritage through its historic landmarks. The Baldwin Home Museum, Lahaina Courthouse, and the Wo Hing Museum are a testament to its past. Explore Front Street's lively charm, where vibrant shops and eateries coexist with historic landmarks. Feel the pulse of Hawaiian culture as you witness traditional hula performances and listen to the sweet melodies of ukuleles. Let the scent of plumeria and the rhythm of crashing waves transport you to a world of pure bliss. 

Honolulu

Rainbow over Honolulu skyline and city.
Rainbow over Honolulu, Hawaii. Image credit Mike Liu via AdobeStock.

Honolulu became the capital of the newly formed Territory of Hawaii after the United States annexed Hawaii in 1898. The infamous attack on Pearl Harbor in 1941 led to the United States' entry into World War II, and today, visitors can pay homage to the events that shaped the war by visiting the Pearl Harbor National Memorial. Dive into Hawaiian culture by exploring historical sites downtown, such as Iolani Palace and the Bishop Museum. Satisfy the taste buds with local cuisine, including fresh poke bowls and melt-in-your-mouth shave ice. Embark on endless adventures in this tropical paradise, whether hiking up the majestic Diamond Head or a scenic drive along the North Shore. 

Waimea

Beautiful tropical waterfall in Waimea Valley park on Oahu island
Waimea Valley Park in Waimea. Image credit ricktravel via AdobeStock.

Captain James Cook first contacted native Hawaiians in Waimea during his Pacific expedition. His encounter with the native Hawaiians marked the first recorded contact between Western explorers and the indigenous people of Hawaii. Today, Waimea is a charming town that blends its rich history, natural beauty, and agricultural heritage. Visitors can enjoy Waimea Canyon, also known as the "Grand Canyon of the Pacific," a stunning sight with red cliffs, green valleys, and waterfalls. Visit Pu'ukoholā Heiau National Historic Site to learn about King Kamehameha I and Hawaiian culture. Local eateries offer fresh seafood and traditional Hawaiian dishes, including attending a luau. Outdoor enthusiasts can hike, explore beaches, and snorkel in Waimea.

Hanalei

Hawaiian canoe sits on the shores of the Hanalei Pier
Hawaiian canoe on the Hanalei pier. Image credit steheap via AdobeStock.

In the mid-1800s, Hanalei Bay became a busy port for the sugar industry. The surrounding areas contained sugar plantations, with workers using the bay to export the valuable commodity. Chinese, Japanese, Filipino, and Portuguese immigrants flocked to Hanalei to take advantage of the economic opportunities. Today, the town has preserved its history and offers enjoyable activities such as surfing, kayaking, hiking, and exploring the Napali Coast. A must-see attraction is Hanalei Falls, where a beautiful cascade of freshwater flows through tropical foliage. The Hanalei Valley Lookout provides panoramic views of the lush taro fields that have sustained the community for centuries and the iconic Hanalei Pier. In Hanalei, every moment is a celebration of island life.

Kohala

Hapuna Beach on the Big Island of Hawaii's Kohala Coast
Hapuna Beach on the Big Island of Hawaii's Kohala Coast. Image credit Kyo46 via AdobeStock.

A region divided into two districts: North Kohala (Kohala's birthplace) and South Kohala (known for its resorts and natural beauty), Kohala carries a rich history that spans centuries. Experience the dramatic volcanic landscapes from above with an exhilarating helicopter tour, ride horseback through lush valleys, or zipline through the trees. Delve into the rich history and culture of the region at the Puukohola Heiau National Historic Site. Hike through the verdant Waipio Valley with cascading waterfalls and taro fields. Discover the awe-inspiring beauty of the Kohala Coast, where pristine beaches meet crystal-clear turquoise waters—snorkel or scuba dive in the vibrant coral reefs, encountering a kaleidoscope of tropical marine life. 

Hilo

Rainbow Falls in Hawaii's Hilo
Rainbow Falls, Hilo. Image credit SCStock via AdobeStock.

An area that established thriving agricultural communities, cultivating taro, sweet potatoes, and other crops in the fertile volcanic soil, Hilo faced its share of natural disasters, including devastating tsunamis in 1946 and 1960, causing significant destruction along the waterfront. However, the resilient spirit of the community led to the reconstruction and revitalization of Hilo. The Lyman Museum features natural history exhibits and cultural artifacts depicting Hilo's heritage. Enjoy a relaxing atmosphere at Hilo's Bayfront and picnic while watching the fishing boats pass by. Hike through lush rainforests along the Hamakua Coast and take in the breathtaking views and waterfalls. The natural beauty, traditions, and customs make Hilo a unique destination.

Kailua-Kona

Hawaiian outrigger canoe at Kamakahonu Beach Kailua-Kona, Big Island, Hawaii
Hawaiian outrigger canoe at Kamakahonu Beach, Kailua-Kona. Image credit Damien via AdobeStock.

Relax on the golden sands of famous beaches like Magic Sands Beach or Kahaluu Beach Park, where you can soak up the warm Hawaiian sun. Embrace the rich history and culture of Kailua-Kona by visiting historical landmarks. Take a stroll along Alii Drive, the town's main street, lined with charming shops, art galleries, and restaurants offering local flavors, or visit the former royal residence, Hulihee Palace, now a museum displaying Hawaiian artifacts and royal memorabilia. Catch prized fish like marlin or tuna during a deep-sea fishing excursion, or if you're feeling adventurous, you can hike to the summit of Mauna Loa or visit the Volcanoes National Park, where you will find volcanic wonders.

Paia

Row of colorful surfboards against palm trees on the beach in Paia
Surfboards on the beach in Paia. Image credit Michele via AdobeStock.

The Paia Sugar Mill became one of the largest sugar mills in Hawaii after being built in 1880. However, in the ’60s and ’70s, Paia quickly became a destination for surfers and others embracing a more alternative lifestyle. Today, Paia offers multiple beautiful beaches for visitors, like Baldwin Beach Park, for swimming, sunbathing, and picnicking, and Hookipa Beach, windsurfing, and kiteboarding. For food enthusiasts, Paia offers an eclectic dining scene from traditional Hawaiian fare to international cuisine. Visitors can either enjoy a peaceful park experience at the Kanaha Pond State Wildlife Sanctuary or study the history of Paia at the Maui Historical Society and the Paia Mill. Discover the magic of Paia!

Koloa

The towering roots of the Moreton bay fig banyan trees from jurassic park in the Allerton Gardens in Koloa, Kauai , Hawaii
Banyan trees in Koloa, Hawaii. Image credit Nina via AdobeStock.

Located on the south shore of Kauai, Hawaii, Koloa established the first sugar cane plantation on the island back in 1835, with visitors able to walk the Koloa Heritage Trail and learn about Koloa’s cultural and historical significance. Adventurous visitors can enjoy a helicopter ride or boat excursion along the Na Pali Coast, whose lush valleys and hidden waterfalls will leave visitors speechless. Nature enthusiasts can visit the stunning Waimea Canyon State Park, which offers beautiful views of the canyon and its vibrant colors. Wind down in the charming historic district of Old Koloa Town with unique shops, art galleries, and delicious restaurants. Koloa is a paradise getaway that offers something for everyone.

Conclusion

Hawaii is like stepping back in time and immersing oneself in a captivating blend of history, culture, and natural beauty. From the picturesque streets of Lahaina, Haleiwa, and beyond, these towns offer a unique opportunity to connect with the island's past and gain a deeper understanding of its roots. Whether exploring ancient landmarks, interacting with friendly locals, or indulging in traditional delicacies, each town presents stories and experiences that will leave a lasting impression.

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