Oliver Compton went from a weeklong sailing camp at Lake Nighthorse in 2018 to sailing nearly 450 miles on the open ocean in just over 28 hours. His boat set a new course record at a 120-year-old race in the process.
This journey is an impressive feat for anyone. Especially someone who hasn’t even had their 18th birthday yet and has a goal to be a professional sailor.
Compton, a Durango native, began sailing at a summer camp in 2018 with a small program called Sail Durango. He was part of a group of around six kids in the junior learn-to-sail program. After the week was over, Compton was hooked.
In 2021, Compton was entering eighth grade and wanted more. He was ready to race. Sail Durango director Katie James took a team to Park City, Utah, to compete in its annual fall regatta. It was a good start, but Compton wanted to take racing much further and be part of bigger racing crews.
Compton had a long road ahead of him if he wanted to compete in bigger events and keep progressing, especially as someone just entering high school. He joined a program called Oakcliff Sailing in Oyster Bay, New York, in May 2024.
Joining Oakcliff meant that Compton was 100% committed; he spent a month and a half sailing in New York from late May to early July. He needed to do extra work at school to be allowed to leave a week before the school year ended. Not only did Compton and his parents have to pay for him to be a part of Oakcliff, but travel and gear are also major expenses for any sailing racer. Compton estimated that his 1.5 months at Oakcliff cost $5,000.
Being part of Oakcliff gave Compton big racing opportunities, but it was no small task. Oakcliff members are training, repairing boats, working out and running errands from around 7 a.m. to 9-10 p.m. every day (later if they do a night sailing practice session). Compton was able to call his parents every couple of days, but he spent almost every waking moment doing something with his fellow sailors.
“We do team workouts and team dinner with tactics,” Compton said. “We’ll do runs together and lifting weights and all kinds of different things. Pretty much everything we do at Oakcliff is with the team. Growing the connections with people is really important because when you're offshore, you have to have a lot of trust in the people on your boat.”
Compton had never done something like Oakcliff on his own. He was homesick for a week as he got used to the new environment, but soon found friends and was caught up in the constant hustle and bustle.
The young sailor’s breakthrough came on June 21, 2024, in the Newport to Bermuda race, a 636-mile race that typically takes three to six days to complete. The Oakcliff boat, Siren, in which Compton was a crew member, won the Stephens Brothers Youth Prize. The prize is awarded to the highest-placing boat with at least half the crew aged 14-23. Siren finished 16th overall out of 150 boats that began the race.
For such a long race, crew members typically follow a four hours on, four hours off work schedule. Managing sails and lines below and above the deck, trimming sails, running hydraulics, steering and navigating are all jobs that must be done constantly and well during a race.
“Most sailboat racing, you don't really see a ton of kids on a boat,” Compton said. “With Oakcliff, you'll see a bunch of under-18 people on boats, so it's really cool that we can do that. It felt pretty special to win (the prize) because I know there aren’t a lot of kids in the world who are going out and doing big offshore races.”
Compton and the other crew members of Siren received a pin and recognition at the race awards ceremony on June 29 at the Pier 6 Complex in Bermuda. Winning the prize is also something Compton can proudly display on his resume as a sailor, which is important as he continues progressing.
Once Compton completed the 2024 Park City Annual Fall Regatta on Sept. 14, his offseason began. Training both physically and mentally is essential for competitive sailors. Compton bikes, skis and goes to the gym regularly at home. He also practices sailing with Sail Durango, setting up racecourses on Lake Nighthorse and staying sharp with the local team. He even traveled to South Carolina during Christmas break to practice ocean sailing and keep up his skills.
Summer 2025 arrived and Compton’s season began as soon as he returned to New York in late May. His breakthrough in 2024 carried over to his first race of 2025. The boat he was crewing, Temptation, took line honors at the Annapolis to Newport race, which began on June 6.
Line honors is a somewhat universal award across sailing that recognizes the first boat across the line before handicaps are applied to determine the overall winner. Temptation was crewed by 16 to 20 people, with Compton in the sewer role. He managed much of the activity below the deck, including lines, sails and water level.
A month later, Compton was back on Temptation on July 6 for the Marblehead to Halifax race. This time, he was the main caddy, an upgrade from the sewer role he played during Annapolis to Newport.
As the main caddy, Compton managed the hydraulics on the boat. A large boat like Temptation needs hydraulics to trim and adjust the sails, since a sail with thousands of pounds of load on it cannot be adjusted by hand.
Temptation had an excellent crew of 19 sailors, including two professional sailors from the America’s Cup, known as the world’s most prestigious sailing race series.
The crew sailed a race that the post-race press release described as “flawless,” breaking the previous course record by just over 45 minutes and setting a new fastest time of 28 hours, two minutes and 56 seconds at the 120-year-old event.
According to Compton, the wind for the race made for perfect conditions and the crew did an excellent job of meshing together to help the boat move as fast as possible. The two professional sailors, Gary Jobson and Dawn Riley (also the head of Oakcliff), did a large portion of the navigating and steering. Seeing them at work was a great learning opportunity for Compton, watching how they surveyed the conditions and made tactical decisions.
Compton is thrilled to add the accomplishment to his resume as he returns home to help run Sail Durango. Since Compton completed his first sailing camp, he has been able help the program grow. He is now a captain, teaching other kids how to sail.
“When I started, there weren't a lot of kids doing it,” Compton said. “I was in a group of maybe six kids doing this program and we had really old boats and everything was a little bit rundown. It’s grown a lot since then and now, when I teach a program or a class, we'll have multiple different programs going on at the same time. There are adult programs and kid programs and I'd say on average, there are about 15 to 20 kids in the weeklong junior sailing program.”
Compton likened his sail racing journey to playing football. Small races like Park City are like playing football in high school, with offshore races like Newport to Bermuda and Marblehead to Halifax being similar to college, the next step up.
His goal is to make it to the sailing NFL, building his resume and getting on a professional-level boat. He hopes to be in a bigger role, like navigator or at the helm on a high-level team, competing in races like the Volvo Ocean Race. The Ocean Race is a five-month, 36,000-mile race with a different course decided for every race. It is considered one of the sport’s ‘big three’ along with the Olympics and the America’s Cup.
However, as Compton continues racing and building his resume, he will also remain focused on the program that launched his sailing career.
“(Sail Durango) is a really cool community, and we're a pretty tight group of friends,” Compton said. “A few of us, we've been doing it together since we started six years ago. So growing the program is really something that makes me happy in life.”
ajbonanno@durangoherald.com
