Mon. Jul 15th, 2024

While your Hawaii itinerary likely includes some of the best beaches and popular spots like Waikiki, spending some time in a small town offers the chance to experience another side of island life — one where you can learn about the area’s history and culture, shop at local farmers markets, sample Kona coffee and island wine, engage with the arts scene, and even live like a Hawaiian cowboy for the day.

Here are eight of the best small towns in Hawaii with a population of 11,000 or less — handpicked by locals.

Old Koloa Town, Kauai

The Eucalyptus Tree Tunnel on Maluhia Road towards the town of Old Koloa, Kauai, Hawaii

Home to Hawaii’s first successful sugar mill, Old Koloa Town on Kauai’s South Shore offers visitors a slower pace and interesting history. Take a self-guided stroll along the 14-stop Kōloa Heritage Trail, shop locally made products at quaint, clapboard-front stores, and cool off with an icy treat made of all-natural, locally sourced ingredients at The Fresh Shave. Tip: Schedule your Old Koloa Town visit for the third Saturday of the month for a chance to taste food truck fare and listen to live music at the night market in Waikomo Courtyard. Or, plan your summer travels to coincide with the Koloa Plantation Days festival in July — a 10-day event that includes cultural activities, sports, and events to honor the diversity of cultures that arrived here during the plantation era.

Haleiwa, Oahu

Twin arched bridge over the river Anahulu in Haleiwa on Oahu

No list of the best small towns in Hawaii would be complete without mention of renowned surf destination Haleiwa. Luckily, you don’t have to be a pro athlete to appreciate the beachy vibes of this town. Located on the legendary North Shore of Oahu, in close proximity to some of the world’s best waves and surf competitions, Haleiwa is just 30 miles — yet worlds away — from the hustle of Honolulu, Hawaii’s state capital. Beginners will feel welcome in the water with expert instructors from North Shore Surf Girls, and spectators can watch locals shred waves from one of the many popular nearby beaches. Spend an afternoon eating and shopping your way around town, bouncing from souvenir stores and art galleries to shave ice stands, food trucks (crispy fish tacos at Surf & Salsa are a tasty way to refuel), and back again before returning to the beach (or an outdoor lanai, like the one at Haleiwa Joe’s) to catch a spectacular North Shore sunset.

Holualoa, Island of Hawaii

Sunset in the area of Holualoa, Kona, Hawaii

If you’re visiting the Island of Hawaii, be sure to schedule a coffee break in Holualoa. Situated between Kailua-Kona and Keauhou in the heart of Kona coffee country, this upcountry small town is surrounded by nearly 600 coffee farms.

“Cradled in the bosom of Hualalai is historic and sleepy Holualoa, remnants of a town where coffee farming families once gathered to enjoy the theater and each other,” says Cindi Punihaole, an Island of Hawaii native and the director of Kahalu’u Bay Education Center, a program of The Kohala Center on the Island of Hawaii. Punihaole notes that Holualoa is one of her favorite small towns in Hawaii. “Today, the narrow country street lined with art galleries shares the artists’ beauty of Kona in all its glory. Let us remind ourselves that this is the Kona we cherish and visit this special place with respect and gratitude.”

Take a guided tour and learn about the Kona coffee beans, from seed to mug. A visit during harvest season (August to December) affords the opportunity to pick coffee cherries from the trees. Visitors can also enjoy art demonstrations and cultural performances during the Kona Coffee Cultural Festival in November.

Makawao, Maui

Historic Village of Makawao in Upcountry, Maui, Hawaii, USA

At the crossroads of paniolo (Hawaiian cowboy) country, this small town is best known for its cowboy culture, friendly locals (which include horses and other ranch animals), active arts scene, and beloved bakery, T. Komoda Store. The fresh pastries and sweets here sell out quickly, so be sure to visit first (except for Wednesdays and Sundays, when it’s closed) for some of their famous cream puffs, guava malasadas, and donuts on a stick before checking out the local art galleries or attending an art workshop at Hui No’eau Visual Arts Center. The upcountry area is also home to long-standing stables, so consider booking a horseback ride to the pasturelands and forests of Haleakala volcano’s slopes, or plan your visit for the Fourth of July, when the Makawao Rodeo, Hawaii’s largest paniolo competition, takes over the town.

He’eia, Oahu

View of the H3 freeway and Koolau Mountain Range on Oahu from east side, He'eia Street in Kaneohe.

Native Hawaiian chef and cultural practitioner Kealoha Domingo says one of the best ways to experience Hawaii and understand the intricate relationship between culture, indigenous food, and management of resources is by “getting to the literal root of it, spending time in a taro patch or an 800-year-old traditional fishpond.” He says this is possible in He’eia, an ahupua’a (a traditional Hawaiian land division that spans from mountains to sea) on the eastern side of Oahu where several community-based organizations, including Papahana Kuaola, Kako’o’Oiwi, and Paepae O He’eia, invite volunteers to support their restoration efforts. In addition, He’eia includes views of Kaneohe Bay and the verdant Ko’olau Mountains.

Volcano Village, Island of Hawaii

Scenic Mauna Kea landscape with paved road to summit between old craters and view on Mauna Loa in clouds.

If you didn’t know this tucked-away town was here, you could easily miss it. Located in a peaceful forest at the doorstep of Hawaii Volcanoes National Park, Volcano Village is home to artists and adventurers looking to be immersed in the powerful energy of the volcanic activity. Take a guided hike through the park, sample some local wine at Volcano Winery, or attend an art or cultural workshop at Volcano Art Center. If you’re in Volcano Village on a Sunday, stop by the farmers market for some locally sourced treats from 6:30 to 10 a.m.

Lanai City, Lanai

Retail Pharmacy in Lanai City of Lanai Island of Hawaii

Although it’s the biggest town on the island of Lanai, Lanai City — a former pineapple plantation village — is very much a small town with just around 3,000 residents. “Lanai is one of the best places in the world to disconnect,” says Lanai Tabura, TV host of Cooking Hawaiian Style and cohost of It’s a Hawaii Thing podcast. Born and raised on Lanai, Tabura says, “It’s not just about the peaceful serenity and endless miles of empty beaches on the island — the quaint town will transport you back in time.” Browse local art or take a class led by a local artist at the Lanai Art Center, drop by the Lanai Culture & Heritage Center to plan a tour (or contact the Four Seasons Resort Lanai for additional cultural activity options led by local experts and practitioners), or simply take a seat at a restaurant and ease into the laid-back pace of this special place.

Honoka’a, Island of Hawaii

Wooden storefronts, such as these in Honokaa, were built during Hawaii's sugar era, as seen on the Big Island of Hawaii.

Wander the main street of this former sugar plantation town on the Hamakua Coast of the Island of Hawaii, and pop into boutiques, eateries (Gramma’s Kitchen is the spot for all-day breakfast), and an antique store. You can also stop by the People’s Theatre, one of the only surviving theaters from the plantation era, as well as Honoka’a Heritage Center, a recently opened museum where you can learn more about the history of Honoka’a and the surrounding Hamakua Coast region. On your way out of town, pick up some sweet malasadas (Portuguese donuts) at Tex Drive In. If you’re in Honoka’a on a Sunday, head to the Farmers Market at Hamakua Harvest at the intersection of Mamane Street and Highway 19 for some delicious food and fresh island produce.


By Lala