Blog: The Windward side calls constantly to this ‘townie’

Jamie Winpenny

Stubborn Boogie
with Jamie Winpenny

I’m a townie. I grew up on the waters and in the parks of East Honolulu between Diamond Head and Koko Head. I spent many weekends and long summer days as a ranch varmint on just about every paddock on Oahu while immediate, extended, and calabash family members rode in rodeos and equestrian shows. But for me, it was always a trip to the country no matter how familiar it became.

“Hawaii Kai,” the Kailua guys would scoff. “It’s the same as L.A. over there.”

“Those Kailua guys make like they’re from the North Shore,” we’d reply. “They’re closer to town than we are.”

So it is with some sheepishness that I now confess a love for the Windward Side. I’m sure my friends have similarly outgrown such provincial biases. Some of them have even defected to the Windward Side, themselves now homeowners in the land of the blond Huns that would occasionally make incursions into the surf spots along our Townie eastern frontier. We’d retaliate, invading their legendary parties and the Makapuu shorebreak. I remember when even inter-zip code dating was scandalous. More recently, I remember feeling a vague sense of betrayal when my sisters (My own sisters!) moved to Kailua.

My invasions into the Windward Side have increased in frequency and duration over the years, my most recent being consecutive afternoons at the Kaneohe Sand Bar aboard the Salty Krak’r. I’ll freely admit to felling like an outsider the first couple of times I went out there, which was only a few years ago. But now, bobbing out there in the pristine waters as people and dogs splash around in the sunlight, I only wonder why it had taken me so long to get out there in the first place.

With the Windward Side just a quick shot over the Pali Highway from where I live in town, I find myself often looking forward to making the trip. I’ve found people and places I enjoy seeing. And it’s about 15 minutes away. I no longer have to worry about some Kailua guy stealing my girlfriend. I golf, swim, and surf out there, visit with family, dine, and even perform out there (although, admittedly, I had a lot more gigs when I was still playing house parties for free beer). I’m a regular at Tamura’s in Aikahi and my aunty’s house is right around the corner.

I may well be a Townie for the rest of my life, but I still proudly reminisce about my days at the many skateboard and surf spots between Diamond Head and Makapuu. My adolescent provincialism is long gone, like a forgotten crush or my first speeding ticket—unless raging house parties ever return to chic for a Gen-X journalist, that is.