The 2006 QuickSilverEdition Molokai to Oahu 32-Mile Paddleboard Race

By Ryan Pingree

Ryan Pingree carries his board up the beach after finishing the grueling 32-mile Quiksilveredition Molokai to Oahu Paddleboard Race, Sunday, July 30, 2006, at Hawaii Kai, Oahu, Hawaii. He paddled for six hours, 51 minutes and 21 seconds, after leaving Molokai. Photo Credit: Bob Cunningham/

I participated in the 10th Anniversary QuickSilverEdition Molokai to Oahu 32-Mile Paddleboard Race last July. The race, which began at Kaluakoi, Molokai and finished at Hawaii Kai, Oahu, is the world championship of long-distance paddleboard racing. A field of 128 paddlers struggled across the blue waters of the Kaiwi Channel, the highest number in the race’s history. Of these 128 paddlers, 36 watermen paddled alone. I was one of them. I trained for over a year for this one day. What follows is my race journal, synchronized to the music I was listening to on my waterproof MP3 player.

10 minutes before the start: Yellow Ledbetter, Pearl Jam

I say aloha to Bill, my captain, and Eric, my crew person, and carefully place my board on the sea. Entering the water, I slice off a dime-sized chunk of flesh from my left hand. I hope it isn’t an omen. Eric later tells me my hand bled the whole way across. I push off and make my way to the start line, the wind gently pushing me into a collection of the world’s finest watermen.

3 minutes before the start: Making Believe, Social Distortion

This is it. I float with my training partner, Jimmy Martindale, at the north end of the start line. It feels good to wear the yellow jersey marking me as a solo racer. It’s a badge of honor but it’s also a sign of high expectations. Yet I’m strangely calm, no butterflies. I smile at Jimmy, “See you on the other side my friend. Let’s do this thing.”

5 minutes: Behind Blue Eyes, The Who

It’s a long race but everyone sprints off the starting line anyway. After a few minutes, I temper my pace and start paddling my own race. On his way to an unprecedented fifth consecutive victory, reigning champ Jamie Mitchell quickly paddles into the building swells. It’s the last I’ll see of him on the water.

15 minutes: Rearview Mirror, Pearl Jam

The chaos and confusion of the start is fading as paddlers settle into their individual rhythms. The arid, rolling landscape of western Molokai falls behind as I drop into the vanguard of the open-channel swells. I look down at the picture of my beautiful, pregnant wife taped to my board, silently urging me on.

40 minutes: The Day I Tried to Live, Soundgarden

A school of flying fish glides ahead of me, escorting the field out of the bay and into the channel. These fish will be the only marine life I see the entire trip, though part of me wants to see a shark, strange as it sounds. When I’m paddling, I know they’re there, lurking in the depths below my belly, checking me out as I glide across their translucent ceiling. As long as I’m moving I have no fear. It’s when I stop and dangle my legs over the side of my board that the bone-chilling music of Jaws fame creeps into my consciousness.

45 minutes: Bro Hymn, Pennywise

Last year Eric and I team paddled the channel and finished in six hours and 42 minutes, good enough for seventh in our division. With a teammate, the Molokai crossing is a fun race. Stock solo, my division this year, is the opposite – a painful, lonesome test of will. Want to have fun? Go with a partner. Want to see what you’re made of? Go stock solo, and good luck to you, for you’re going to need it. A solid crew person is an often-overlooked critical component of a successful crossing. I’m lucky to have Eric in that capacity, keeping me on course, focused, hydrated, and motivated. He claims to have a bag of pebbles he’ll hurl at me if I lag. I don’t doubt it.

1 hour, 5 minutes: Real Situation, War Called Peace

I’m having a blast so far. The bumps are great and I’m connecting runs … two, three swells in a row. Up on my knees, stroke, stroke, glide, glide … six miles under my trunks already and I feel strong. I’m paddling near a team and we surf down the swells on our knees side by side. We share the energy and hoot, urging each other on. I remember reading somewhere that everyone has fun for the first three hours of Molokai. It’s the last three or four or five or – please, oh no, please no – six hours to be worried about … They certainly do me.

1 hour, 10 minutes: I Ain’t Wasting Time No More, Allman Brothers Band

For the first time I can see my goal, Koko Head, a prominent 642-foot high volcanic bump on Oahu near the finish. … Koko Head. Got to make Koko Head.

1 hour, 45 minutes: Leash, Pearl Jam

I wish it were wild enough so that I needed my leash today. But conditions have dampened dramatically from yesterday’s 25-plus knot winds and 6-foot waves. It’s going to be more of a shoulder-burning paddle than a surf-assisted glide to Hawaii Kai. I drop the leash and hope I prove to be man enough.

2 hours, 10 minutes: Three Little Birds, Bob Marley

“I’m still having fun!” I yell to Eric and Bill. Over two hours in and Eric tells me I’ve plied through 12 miles of deep blue Pacific water. I feel good and keep my energy output at about 80 percent of maximum. Anything faster and I’ll burn out; anything slower and I’ll lose focus and flail. Bob’s mellifluous voice relaxes me and I smile. “Every little thing, is going to be all right …”

2 hours, 40 minutes: Mutt, Blink 182

Eric calls out that I’ve covered 15 miles. I do some quick math and come out with an estimated total of just under six hours, much faster than my goal of seven. That’s hot, bruddah! I pop up to my knees again and lock into a nice bump.

2 hours, 55 minutes: Up Here in My Tree, Pearl Jam

I’m alone now with the bulk of the paddlers behind me. My nearest competitors are well north and south of me. It’s amazing how quickly the field separates as each takes their own course, convinced they have the perfect line when there is no perfect line. I’m no different. I trust my instincts and aim for just south of Koko Head, against the judgment of my crew and their trusty GPS.

3 hours, 15 minutes: Thunder Road, Bruce Springsteen

I’m paddling my hand-shaped custom Pang board, which I’m convinced has a soul. I’ve had it for more than two years and it seems to have been created just to reach out and glide over this channel. While on a training paddle earlier in the year, I hit a coral head and put a severe ding in it. At the time, I figured I’d never use my Pang for Molokai, as the foam had sucked up water. The board felt heavier and slower. But a skilled craftsman fixed it near as good as new. Today we are paddling as one.

3 hours, 45 minutes: Doesn’t Remind Me, Audioslave

My pace has slipped. The wind has slackened significantly, leading to a decrease in wave size and thus more paddling, less gliding. Whitecaps are few and the waves are down to two feet. I’m feeling the first waves refracted off Oahu. It’s getting messy. A mental wall of doubt is building, brick-by-brick. Koko Head heckles at me from afar, daring me to keep paddling. “Give up, son, you’re weak! Just paddle over to the boat and hop in. Quit!” I tell myself just make it to four hours and I’ll be fine. “I’m going to make it!” I yell at Koko Head in the distance.

4 hours: Mayflower, Homemade

Eric says I’ve hit the 20-mile mark; only 12 or so to go. My right arm has cramped up once and my left groin is sore, but other than that, I’m solid. A large bulk cargo ship cuts through the channel from north to south, sounding her horn. The tonnage rule is definitely in effect out here today and she sure as hell isn’t slowing or altering course for 12 feet of foam and fiberglass. In spite of all of her mass, the sea swallows her wake before it hits me. I look down at my wife’s picture and drop into a nice bump. The best bumps seem to come when I need them the most.

4 hours, 45 minutes: Big Strong Man, Clancy Brothers

The bottles clanking in the background of this song make me think of the Guinness awaiting me on the beach in Hawaii Kai … and how I’ve said “nay” to offers of beer all summer thinking it would make me a faster paddler. I questioned my strategy on many a Saturday night, but I stuck with it. If the Big Strong Man came along now, I’d surely let him drink all the water in the sea and I’d walk all the way to Oahu.

5 hours, 25 minutes: Need to Know, Pennywise

I have seven miles to cover to reach Portlock at the base of Koko Head. Once there, it will be a little over a mile to the finish. The chop is at its worst yet, but I’m dropping into more runs than I have in the previous two hours. According to Eric, I’m still alone; the nearest paddler is approximately a quarter mile south. Sensing that I have the energy to finish competitively, they’re urging me to reel ‘em in.

5 hours, 45 minutes: Getting In Tune, The Who

This is my paddleboard anthem. I read a few years back that hand position and technique is as important, if not more important, than brute strength and endurance. So in my training I’ve concentrated on proper positioning and technique. Doing so reduces the side-to-side motion at the nose of the board, and hence wastes less energy. By concentrating and creating muscle memory, I’ve gotten in tune and trained myself to paddle “straight and narrow.” … For the first time, I can make out the radio towers and individual trees of Koko Head. Now, I’m 100 percent confident that I’m going to finish. I pop up to my knees and sing aloud; I’m in tune.

6 hours, 11 minutes: STP, Sublime

I catch up to a few paddlers as we converge on Portlock. Paddlers to the north have run into the current pushing up channel and the groups to the south are fighting against the swells up to Portlock. I believe I’ve chosen a near-perfect course across the channel. I can smell the finish. All of a sudden, there are boats, paddlers, jet skis, and surfers everywhere. I should finish in 30 minutes, but …

6 hours, 14 minutes: Chumbawamba, Tubthumbing

Suddenly, the current is knocking me down. I’m almost around the corner at Portlock and I’m going backwards. Working at about 90 percent effort, with the wind and waves at my back, I expected to shoot around the corner and head for the finish. Instead, I’m watching the cliff face move slowly past – in the opposite direction! Paddlers just outside of me seem unaffected. After struggling stubbornly for a while and cursing up a storm, I finally get smart and paddle at a right angle to the current, toward the wall. Close to the wall, the current releases me. Energized by this final hurdle, I jam around the corner.

6 hours, 40 minutes: When I Come Around, Green Day

I’m in the calmer waters of Maunalua Bay, finally. The wind is light offshore, blowing in my face and kicking up small four-inch swells. I’ve taken an outside course to the finish, foregoing the risk/reward of catching a south swell into the beach. Damned if I’m going to paddle 31 miles only to wipe out so close to the finish. I want to beat seven hours so I pick up my pace.

6 hours, 54 minutes, 21 seconds: Click Lips, Blink 182

On my knees, I take a final stroke and cut my hand on a rock just beneath the surface. It seems appropriate that I’ve given the ocean a piece of myself at the start and finish of my crossing. A toll, perhaps, for my successful passage? … I’m tired but not exhausted. I let out a yell of pure stoke and glide to the beach. I stand on the beach and look for my wife. She’s in the crowd, smiling. I turn off my music, gently place my board in the grassy shade, and hug her, all pau. I walk away from the crossing holding Jaime’s hand, ready to begin my next challenge – fatherhood.

Much to his surprise, Ryan’s time was good enough for second place in the men’s 30-39 Stock Solo age group. His wife delivered their first child, a baby girl, 11 days after he crossed the Kaiwi Channel. She has the long arms of a paddleboarder and the future is hers.