The Quirkiest Town In Hawaii That You’ll Absolutely Love
By Megan Shute|Published November 16, 2017
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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.
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 killer beaches, art galleries galore, adorable shops, and stellar vacation rentals. It is also the quirkiest town you’ll find in Hawaii — perhaps due to its eclectic collection of shops and restaurants, or maybe it’s the plethora of street art you’ll find around every corner. Let’s take a look:
Serving as the gateway to Oahu’s famous north shore, this quintessential Hawaiian town established in 1898 when businessman Benjamin Dillingham opened a hotel on the north shore and named it Hale’iwa.
And while you’ll find countless stellar art galleries as well as the Annual Haleiwa Art Festival (which takes place every July), it is the street art that truly gives Haleiwa its quirkiness.
To truly appreciate the quirkiness that is Haleiwa, you’ll want to visit for yourself. Make a day trip of it: start your morning with a cup of joe from the Coffee Gallery or an acai bowl from Haleiwa Bowls.
Full of killer surf shops, cute clothing boutiques, souvenir shops and specialty stores, the Haleiwa stretch of Kamehameha Highway is home to some epic shopping.
Grab a bite to eat at one of the town’s many food trucks or sit-down restaurants, depending on your preferences.