9 Towns In Hawaii With The Best, Most Lively Main Streets
By Megan Shute|Published January 15, 2018
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Megan Shute
Author
With more than 10 years of experience as a professional writer, Megan holds a degree in Mass Media from her home state of Minnesota. After college, she chose to trade in her winter boots for slippahs and moved to the beautiful island of Oahu, where she has been living for more than five years. She lives on the west side but is constantly taking mini-road trips across the island and visits the neighboring islands whenever she can getaway. She loves hiking, snorkeling, locally-grown coffee, and finding the best acai bowl on Oahu.
There is little better than strolling through one of Hawaii’s most charming towns on a bright and beautiful island afternoon. Even better, is strolling down a lively main street home to countless incredible restaurants, charming boutiques, eclectic galleries, and more. These nine towns found across the islands — from Kauai’s northern shore to Hawaii Island’s southeastern coast — are home to lively main streets perfect for a relaxing day of exploring.
Now, just to be clear: none of these 9 incredible towns have main streets that are actually named “Main Street,” but the traditional Hawaiian street names certainly contribute to their charm.
Located along Hawaii Island’s scenic Kona coast is Kailua-Kona, a historic seaside village full of natural beauty, royal history, and plenty of charm. Established by King Kamehameha I to be the seat of his government when he was the chief of Mona before he consolidated rule of the island chain. The historic town later became the capital of a newly unified kingdom, before it moved to Lahaina, and later, Honolulu. For the best shopping and collection of restaurants in Kailua-Kona, head to Ali'i Drive, park, and take a leisurely stroll along this seaside street.
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. The main highway that runs through town, Kuhio Highway, is home to many of Hanalei’s greatest destinations, including Wishing Well Shave Ice and Bar Acuda.
Once a crazy whaling town and the original seat of Hawaiian royalty, Lahaina has since been tamed and is now full of restaurants, surf shops, boutiques, and galleries lining the city’s Front Street. Oh, and did we mention that Front Street overlooks the beautiful Pacific Ocean as well? Yep, the views are pretty phenomenal!
Voted as the state’s favorite small town by Hawaii Magazine, Haleiwa seems like a world away from bustling Waikiki. This sleepy surfer town has a laid-back vibe and charming aesthetic, but also luxuries like great restaurants and adorable shops — all found along Kamehameha Highway, of course.
Often described as one of Hawaii Island’s best-kept secrets, Hawi is perched along the northern coastline of the Kohala coast, and is home to a pretty charming vibe. Two decades ago, a new generation of entrepreneurs and artists flocked to the former plantation village and, with the help of longtime residents, moved bookstores, galleries, boutiques and restaurants into the town’s decaying storefronts along Mahukona-Niulii Road. Now, this lively main street is one of the best places to shop and grab a bite to eat on the entire island.
Home to Hawaii’s first ever commercially successful sugarcane plantation, Koloa is a relic of days gone by. Home to less than 2,200 residents and shops that now occupy the plantation-style buildings, Koloa is located along Kauai’s southern shore. You’ll find all of the action on Koloa Road.
Just four miles from Kahalui on Maui’s famous Road to Hana is Paia, a small beach town big on charm. The town is not only known for its epic surfing and windsurfing waves, but is the epicenter of Maui’s north shore, and is full of artsy, bohemian vibes. While the adorable seaside town is gaining traction with tourists, it is still often seen as merely a spot to refuel, grab some food, and head out on the Hana Highway.
Nowhere will you find a more lively street than Honolulu’s Kalakaua Avenue. This bustling street that meanders through the heart of Waikiki is home to world-class restaurants, shopping, and hoards of tourists. It’s easily the busiest street on this list, and whether or not you like crowds, it’s one Hawaii destination you’ll want to check out at least once — if only to experience the infectious energy.
With a population of approximately 43,200, Hilo is the state’s fourth largest city. Unlike many big Hawaiian cities, Hilo has never experienced huge tourist draws, which means it has stayed true to the state’s pre-World War II persona, and is full of plantation-style architecture and historic storefronts, especially along the town’s main street, which is known as both Mamalahoa Highway and Kamehameha Avenue.
How many of these charming “main streets” have you visited? Are there other main streets you would add to this list? Share your thoughts and opinions with us in the comments below.
And if you’re more into sleepy rural communities than you are into lively main streets, you’ll want to visit these 13 rural towns in Hawaii oozing with charm.
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