Eight Years in the Making
Back in June 2018, a bunch of us were waiting at the Orcas-to-Anacortes ferry terminal after ToorCamp, a hacker camp at Doe Bay. A guy walked up with a long sea kayak on wheels, packed for a multi-day trip. Of course, I had to ask about it. He told me that every year he parked in Anacortes, paddled around the San Juan Islands for a week or two, and then caught a ferry back.
I loved the idea. From that moment on, I wanted to walk my own kayak onto a ferry.
Fast forward eight years. My paddling buddy Jim, Team Wind and Waves and Water from the Seventy48, asked if Mary and I wanted to spend the weekend in the San Juan Islands on his big boat. Oh, and while we were there, Jim and I could race the Round Shaw Race. It is a 14-mile loop around Shaw Island, and each racer gets to choose clockwise or counterclockwise. Rough water and strong tidal currents are usually part of the fun.
Mary and I had been talking about paddling in the San Juan Islands for a couple of years. She had never been, and I had not been back since last year’s WA360. A weekend on a boat, a new race, and finally getting to put our kayak on a ferry? We were in!
Getting There
Jim and I would race in our matching Stellar S18 Expedition G2s, so I took mine down to his house and loaded it onto his boat. He planned to motor north early Friday morning. Mary and I would drive up separately, which meant we could head home Sunday afternoon.
Taking a car onto a San Juan Islands ferry means getting a reservation or taking your chances with standby. Walking on with a bike or kayak is much easier. No reservation required! On Friday, August 21, Mary and I drove to Anacortes, unloaded our Delta Traverse 17.5T tandem and all our gear near the walk-on building, bought two tickets to Orcas Island, and paid the extra fee for the kayak. I parked the car in Upper Lot D, and then we waited.
Only eight years after meeting that kayaker on Orcas Island, I was finally walking my own kayak onto a ferry. Better late than never! :)
When we arrived at the Orcas Island ferry terminal, we were the last people off the boat. The ferry employees helped us at every step and made the whole process incredibly easy.
There is a public boat ramp right beside the Orcas Island ferry terminal. Getting a 17.5-foot kayak, wheels, and all our gear down the ramp took a little work. Okay, maybe more than a little. But we got it into the water!
From there, we paddled 3.5 miles to Deer Harbor, where Jim and his wife were waiting on their boat. Not a bad place to call home for the next two nights!
About halfway to Deer Harbor, we paddled through Pole Pass.
Race Morning
Saturday morning came way too early. Before we could race 14 miles around Shaw Island, Jim and I had to get our boats from Deer Harbor on Orcas Island to the starting line at Indian Cove. That added a 4.5-mile paddle before the race even started. It took us 1 hour and 9 minutes.
We paddled across to Blind Bay, which gave us a shorter crossing. From there, we put the kayaks on their wheels and walked them a mile and a half across the narrowest part of Shaw Island to the starting line. Because apparently a pre-race paddle was not enough of a warmup.
At the starting line, we caught up with Tom and Lock. Tom is half of Team OctoCosta from the Seventy48. He and Lock paddle together often, and they had entered the race in a tandem sea kayak.
The race started at 10:15 AM on Saturday, August 22. First, we signed the obligatory “the race organizers are not responsible, and I definitely know what I am doing” form. I got boat number 3, and then we attended the race meeting to go over the rules and hazards. The big decision was which way to go around Shaw Island. Clockwise or counterclockwise?
Picking a Direction
The tidal currents made counterclockwise look like the obvious choice. The current would be in our favor for about 8.3 miles. That left roughly 4 miles against as much as 1.8 knots of current along the southwest side of Shaw Island.
Then there was the wind. It was coming from the south at around 10 knots, with gusts up to 15. Those four miles against the current were also going to be straight into the wind. Fun!
When the organizers asked which way everyone planned to go, the teams split about evenly. Jim, Tom, Lock, and I all chose counterclockwise. Time to find out if we had done the math correctly.
Around Shaw Island
For the first 8 miles, counterclockwise was a blast. There was barely any wind, and the current pushed me along at more than 7 mph at times. I was feeling pretty smart about my choice! Around the halfway point, I started passing the teams coming the other way. There was also plenty of motorboat traffic to keep things interesting.
Then I rounded the westernmost point of the island and turned straight into the wind and current. So much for feeling smart. My speed dropped fast. I tucked into the bay to get away from the current, but that only helped so much. The wind was still waiting for me.
Around the south point of the island, the water got squirrelly in a few places. At one point, I was moving about 4 mph when I hit a patch of current that felt like a wall. I paddled as hard as I could and watched my speed drop to 2 mph. Then, just as suddenly as I had entered it, I broke free.
Then I hit a section of huge standing waves. I had never paddled through anything like them before, and it was so much fun!
The Finish
By the final two miles, I was spent and slowing down more than I wanted. Then I saw the two OC6 teams coming toward the finish from the other direction. Nothing finds a little extra energy in tired arms like seeing two fast boats about to beat you to the line. I pushed hard and crossed just before they did.
I am pretty sure the only reason I beat them was that I went counterclockwise and they went clockwise. Those fast boats would have left me in the dust under equal conditions. I will still take the win. :)
I finished in 2:52:17.8, 10th out of 17 teams. Not bad after paddling 4.5 miles and walking another mile and a half just to get to the start! The full Round Shaw 2026 results are available on Webscorer.
| Place | Finish Time |
|---|---|
| 10th of 17 teams | 2:52:17.8 |
Back to Deer Harbor
After the race, Jim and I caught up with Tom and Lock for a bit. Then it was time to put the boats back on their wheels and walk another mile and a half to Blind Bay.
From there, we paddled another 4.3 miles back to Deer Harbor. That took about 57 minutes. Between the race, the paddles to and from Shaw Island, and all the walking, my arms and legs had both gotten their money’s worth.
That night, Jim’s wife made us an amazing dinner. Afterward, we took a walk around Deer Harbor. Much better than sitting in a kayak!
Heading Home
Sunday, August 23, Mary and I got up early, packed everything, and got back on the water in time for the 8:55 AM ferry to Anacortes. Somehow, the wind and rain stopped right when we needed to launch. We had a calm paddle back to the Orcas Island ferry terminal.
We rolled the kayak up to the walk-on area just as the ferry came into the terminal. Perfect timing!
Huge thanks to Jim and his wife for inviting us and letting us call their boat home for the weekend. We had such a great time!
And, as always, a huge thank you to my amazing wife. Mary, I love being on the water with you so much. Even hauling a 17.5-foot kayak through a ferry terminal and down a boat ramp is fun when we do it together. I cannot wait for our next adventure!