STONEHAM, Mass. – David Sinclair was hot on the heels of Patrick Caron for nearly every step of 32 miles at the Fells Winter Ultra on Saturday, Dec. 1, at the Middlesex Fells Reservation.

For the better part of four eight-mile loops of the rugged Skyline Trail at the more than 2,500-acre public wildland seven miles north of Boston, Sinclair followed a few strides behind Caron. It was smart strategy. The 26-year-old resident of Peru, Vt., was running at the Fells for the first time. Meanwhile, Caron, a 21-year-old from Needham, Mass., knows the loop as well as anyone, having won the event’s 40-mile race in 2015 and 2016.

Although they ran in close contact for so many miles, a fierce battle wasn’t taking place. Caron opted for the 32-mile race this year; Sinclair was entered in the five-loop, 40-miler. What unfolded was a display of teamwork that worked to the benefit of both trailblazers. Sinclair pushed Caron for four loops while the local standout helped the newcomer learn the course’s twists and turns. In doing so, both hammered the rocky, root-covered singletrack trails ahead of course-record pace and helped each other rewrite the history books at this classic New England ultra.

Caron and Sinclair both began the day with records in mind. Caron knew Kyle Pietari’s 32-mile mark of 4:43:52 from 2015 was beatable; the two ran most of their miles together that day when Caron was a young 18-year-old racing just his second ultra. Meanwhile, details of the true 40-mile course record required a bit more digging as the event has roots as an unofficial race in its pre-TARC Race Series days. Josh Katzman set the standard with a scorching 5:48 during those “old school” days, a mark that was challenged but not surpassed when Scott Traer hammered a 5:57 at the 2011 event. Those were the only two sub-6-hour performances prior to Saturday.

Katzman shared his record-setting splits (1:02; 1:02; 1:06; 1:17; 1:21) with Caron and Sinclair to help them strategize. In addition to Katzman’s statistics, Sinclair benefitted from a quick tutoring session from Caron regarding the course. Sinclair admitted that he didn’t realize exactly what he was getting himself into when Caron informed him the night before the race that runners are allowed to choose which direction they want to run the course.

“He said he was going to go counterclockwise, so I decided I was going to go with him,” Sinclair said.

Homework done, the two got to work bright and early Saturday morning when race director Jeff LeBlanc sent the runners down the trail. Caron led the way; Sinclair followed close behind.

“I let him take it out, so he pretty much led the way for the first four laps and I was just trying to follow along with him,” Sinclair said. “He was moving really fast and knew most of the turns; we took a couple 30-second detours when we missed the white blazes, but it was nice to run behind him. He was flying out there today, so I was just trying to hang on.”

They wasted no time moving ahead of record pace.

“The first two laps (Katzman) went out in 1:02 and I was like ‘damn that’s fast,’ and then we went out in 59 minutes,” Caron said. “I was surprised by that just because I never really felt like going fast before because I figured I was running further and should pace myself, but it just made the miles fly by running with David.”

They rattled off nearly even splits, finishing the first loop in 59 minutes, the second in a few seconds shy of an hour, and the third in 1:03.

While they were out in front, they unknowingly faced some close competition for front-runner status for a few loops. In the 40-mile race, defending champion Isaac Burleigh and Ryan Wooley ran together in the clockwise direction. They rolled through the first loop in 1:03 and the second in 1:06, putting them 10 minutes behind Caron and Sinclair. Both fell off the pace in the third loop, however, and ultimately dropped after completing 24 miles.

While Caron had the 32-mile record well in his sights heading into loop four, Sinclair wondered whether he could hang on for two more laps of the challenging course with its rolling hills and rocky climbs amounting to around 1,700 feet of gain per loop.

“From a fueling standpoint I figured I might run out of energy on that last lap,” Sinclair said. “Sure enough, about 3 1/2 laps in all of a sudden it got way tougher to get up those hills. I knew if I got dropped by Patrick it would get a lot tougher mentally, so I was able to just stay right behind him until the end of that fourth lap.”

They once again stuck together on loop four, this time covering the course in 1:07. Caron led by a few strides and dashed across the finish line in 4:09:53, smashing the 32-mile course record by 34 minutes.

Sinclair finished the loop 10 seconds later, refueled and headed back out for more.

“It got tough that last lap,” Sinclair recalled. “The fifth lap I was on my own and I didn’t know where any of the competition was anymore. I sat down once or twice and took a minute breather, got in an extra little bit of food and water and tried to keep on moving.”

Ultimately, Sinclair’s final loop took 1:19. It was his slowest of the day, but it was still plenty fast enough to achieve his goal. As he covered the final 50 yards to the finish line, he raised his hands to the sky with an exhausted smile on his face. Katzman was there to greet him and congratulate Sinclair for his record-setting effort of 5:29:48.

The win was the fourth of the year at an ultra distance for Sinclair. His prior wins came at the Speedgoat 50K in Utah, the Ragged 50K in New Hampshire, and the Killington 50K in Vermont.

The race for second place in the Fells 40-miler was a battle of attrition. While Burleigh, 28, of Socorro, N.M., and Wooley, 29, of Brighton, Mass., were in the hunt for a few loops, once they dropped it became a three-person race for the runner-up spot between 31-year-old Christopher Watson of Cambridge, Mass., 30-year-old Christopher Knighton of Allston, Mass., and 34-year-old Johan Keller of Malden, Mass. Watson and Knighton also dropped after three loops, leaving Keller to endure a fourth loop and secure second place in 7:09:46. Austin Black, 28, of Intervale, N.H., rounded out the men’s podium by finishing third in 8:06:41. Of the 31 runners, including 23 men, who started the 40-mile race, 14 men were among the 19 runners who ultimately finished.

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Meanwhile, the race for second place in the 32-miler was determined early. Defending champion Michael Pulli, 42, of Medford, Mass., ran a 1:06 first loop and a 1:08 second loop, putting him 15 minutes behind Caron but 11 minutes ahead of anyone else. He continued to expand the gap during the second half of the race and went on to finish as the runner-up in 4:54:14. Pulli’s time was good for third on the course record board, and it was a 16-minute improvement on his winning effort from 2017. Iain Ridgway, 38, of Grantham, N.H., rounded out the men’s podium in 5:08:01, followed by 25-year-old Davis Cutter of Brookline, Mass., in 5:19:43. They were the lone men to finish in less than six hours. Of the 67 runners who started the men’s race, 54 finished within 10 hours.