The Quirkiest Town In Hawaii That You Ll Absolutely Love

The Hawaiian Islands are home to countless incredible towns, from tiny towns with less than 500 residents to those with thousands of residents that somehow still feel charming and quaint. And while all of these Hawaiian towns and cities are fantastic, there is no greater town than Haleiwa, a charming surfing community located on Oahu’s famous north shore.

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.

tdlucas5000/Flickr

This little Hawaiian town is not only full of history — but a vibrant creative spirit that makes this surfing mecca something special.

Anthony Quintano/Flickr

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.

Marko Forsten/Flickr

From the iconic angel wings found in front of Anahulu’s Shave Ice…

Nadine C./Yelp

…to this Bob Marley mural and everything in between, nothing beats Haleiwa’s art scene.

Suzanne W./Yelp

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.

Haleiwa Bowls/Facebook

Coffee Gallery Hawaii/Facebook

Stroll down Kamehameha Highway and visit all of the shops your heart desires.

Igiss/Flickr

Anthony Quintano/Flickr 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.

Brian D./Yelp

Katherine A./Yelp Two of our favorites are the Haleiwa Beach House for epic sunset views and Dat Cajun Guy for mouthwatering shrimp.

Paddle board down the Ahahulu River in the afternoon.

Tyson C./Yelp

Sample shave ice at the famous Matsumoto’s.

Albert Lynn/Flickr

And as with any day in paradise, end your quirky day trip with a sunset over the Pacific Ocean.

Kanaka Rastamon/Flickr

Did you know that Haleiwa is also home to countless mouthwatering restaurants? Come for the food, stay for the quirkiness.