Otillo Casco Bay World Series - When the Side Quest Interrupts the Main Quest
Since I started participating in endurance sports 18 years ago, I’ve had the single goal of becoming invincible. As silly as it sounds, I like to think there is no challenge that I can’t take on.
The last year has had me reevaluate this. Sometimes I don’t want to be the strongest person in the room … and it’s ok to lean on family and friends for support and to get you through tough times … and for that I will be forever thankful.
Two weeks ago, I took on a new challenge that I thought would test me to the core … but as life would have it I was able to grind this out without too much trouble. Even with severe tendinitis within my left wrist, I muscled through. Have I become too hardened for my own good? Only time will tell.
Three days after my race my left wrist was still really bothering me so I called the doctor. As luck would have it, I got an appointment that morning with Kaitlin, the physician assistant that I normally see. She is very familiar with my ultra exploits and says she even tells her other patients about me. Lol.
The diagnosis, tendinitis with the possibility of a bone spur. This wasn’t supposed to happen. This was the side quest. Since I started ultra running in 2011 I have been repeatedly told to cross train … and my first race that includes another sport and I injured myself? Are you kidding?
Below is the story of my first swim run: 27 legs with 5 miles of swimming and 16 miles of running through the islands of Casco Bay.
Becca wasn’t back to running yet but was happy to swim as much as possible. So we started hitting up the Mystic Lakes a few days a week. We started with some quarter mile swims, then progressed up to a ½ mile and eventually to 1.2 miles. To keep it interesting we also swam at Walden Pond and Pleasure Bay at Castle Island / Fort Independence). Keith started joining us and we got in a groove: Monday Mystics, Walden Wednesdays, and Fridays at Fort Independence.

The Otillo races include many, many legs. You effectively swim from Island to Island and then run across them. They get you off road as much as possible and often involve climbing over rocks. Since they generally take place in the ocean, wetsuits are required, and since you transition many times, you end up running in your wetsuit … a shortie wetsuit. And since you swim with your shoes on, you are allowed to use a pull buoy to help keep your feet afloat.
After a few weeks of swimming, I started my swim run specific training. I would swim across the lake, then run around, and then repeat. At the peak of my training, I swam a ½ mile twice and surrounded it with 3 by 2 mile running legs.
Race day was August 9th and Amy and I headed up to Portland the night before and caught some of the Heart of Pine’s soccer game. Race morning started very early as I had to catch a 4:30 ferry out to Great Chebeague Island.
On the ferry ride out, I met two long distance swimmers (really one has swum 24 miles around Little Cayman Island) and we chatted for a while. There is quite a bit of overlap in marathon swimming and ultra marathon running. They joked they would see me as I passed them on each run leg. I think I caught them 4 or 5 times before they finally got away on one of the longer swims.
After a short fog delay, we started the race at 6:20. The first leg was a simple 1 mile run with about half of it on the soft sand beach. The first swim was equally as short being about a quarter mile from one point to another.
The second run leg, about 2.5 miles, I found my stride and really started to run away from the crowd only to get caught by most of them on the following swim leg. This pattern repeated for the next few legs. While I wasn’t moving fast, I was solidly in the top half of the field and feeling pretty good.
When I estimated my time before the race, I figured I would be somewhere in the 6:30 range. I was probably in the top 10-15% of the runners, but in the bottom 10% of the swimmers. Most of these folks have been swimming for a long time or are doing Ironman triathlons. I was a bit of an outcast as the ultra runner that tried to pick swimming back up after a long hiatus.
Leg 10 might have been my favorite leg in the whole race. After just over a half mile swim, I got out of the water to realize that I had about a 25 yard crossing of sandbar before I had to swim again. Nonetheless, I tracked the super short leg on my GPS watch to which my friend Robbie said “Appreciate the commitment to accurate Strava records.”
Leg 11 was a circumnavigation of Vaill Island where you were 100% on the rocky shore and brought back great memories of rock hopping as a kid.
After finishing legs 12 and 13, I was feeling really good about myself. 2:20 minutes in and already almost half way there … but that doesn’t really tell the story. I had run about 9 miles so far, but only swam about 2500 of the 9000 yards. So, no, I was not half way there. Not by a long shot.
Leg 14 was the “long” swim leg clocking in at just under a mile. This is where my lack of swim training and experience started to get me. After 36 minutes, I finally reached the other side. This is also when my left wrist really started to bother me … but I was on an uninhabited island in the middle of the bay, so I soldiered on.
I got just a .72 mile run break before I had to swim over to Great Diamond. This is also when I became a little unsure of my ability to complete this race. There really was minimal support between islands and as I became tired, my sighting started to suffer and my ability to swim a straight path went down hill.
Thankfully, when I got to leg 21, I was greeted with the “long” run leg at 3.75 miles. After a quick wrong turn, I regained my composure and found a groove.
The last few legs were a bit of a bear; the run legs were short and the swim legs were long (or at least longer than I wanted). As I approached the final swim leg, I could see Peak’s Island and its ferry terminal. Unfortunately the time was starting to go out so I would have to fight the current.
After what seemed like forever, I finally stood up on the beach. Amy was there waiting for me and I had just a few hundred yards to go to finish.
– 27 legs, 5 miles of swimming (most in a day by ~1.5 miles, 16 mile of gnarly trails and rocks, 7 hours, 1 minute –
After a bite to eat and a cappuccino, Amy and I caught the ferry back to Portland and headed home.
All and all, a great and challenging experience. Was 5 miles of total swimming more than I was ready for? Yes. Was I able to lean on the grit I gained in ultra running and life in general? Absolutely.
- Scot
Addendum, after about two weeks of wearing a wrist brace and taking it easy my wrist is feeling much better. Doctor’s appointment to follow up soon.

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