Chris Barry started running at 6:23 p.m. Friday.

He logged 23 miles before going to sleep that night, a heavy workload for even the most seasoned long-distance runners.

The next day, the Keene resident ran 67 more. And he wasn’t done.

By mid-morning Monday, Barry, 40, had covered 150 miles in all — roughly the distance from Keene to Boston and back, as the crow flies.

The effort earned him a top commendation in Satan’s Sidewalk, a first-time event organized by Berkshire Ultra Running Community for Service in which participants can choose to complete either a 66.6-kilometer race or as many miles as possible in 66.6 hours. The event takes its title from a nickname for the treadmill, which is how runners typically complete BURCS’ winter challenges, according to Barry.

However, the Pittsfield, Mass.-based organization added an outdoor option this year, with many gyms closed or at limited capacity due to COVID-19 — though it encouraged people to stay within a mile of their homes. BURCS describes Satan’s Sidewalk on its registration website as a run “through fire, brimstone, and masochistic purgatory.”

Barry, who chose the timed option, where the clock does not stop while participants sleep, eat or use the bathroom, said his biggest challenge was battling boredom during nearly 300 laps of a 0.52-mile loop near his Page Street home.

That included “lots of funny looks from the neighbors,” he said.

“They know I’m a runner. I don’t think they knew how crazy.”

An English teacher at Keene High School, Barry said he has always enjoyed running and began competing in ultra-marathons — longer than the standard 26.2-mile marathon — about six years ago. At the time, he taught at Keene Middle School and coached track and cross country.

One of his first events, in July 2015, involved running a 3.2-mile loop as many times as possible in 24 hours. Barry ran for 14 hours and covered 64 miles, according to previous reporting by The Sentinel.

Since then, he has completed four 100-mile races — three of them the Vermont 100, a prominent ultra-marathon that starts in West Windsor, Vt. He planned to run three events last year, including the Vermont 100 again and the Drummer Hill Trail Race, a 50-kilometer run in Keene, but they were canceled due to the pandemic.

BURCS is well-known among local ultra-marathoners, according to Barry, who said Satan’s Sidewalk appealed to his fondness for absurd challenges. (The event mascot, “Wally,” is a humanoid watermelon.)

“When I saw this one come up, I was like, ‘This is totally stupid and pointless, and I’m totally going to do it,’ ” he said. “… It’s written to appeal to idiots like me.”

Although Barry prefers trail running to paved surfaces and treadmills, which put more stress on his body, he stuck to the road over the weekend: His route went down Page Street and Beaver Street, up Washington Street and past Franklin Elementary School on Greenlawn Street.

Knowing that the 66.6-hour challenge would include two nights, no matter how he scheduled it, Barry began running Friday evening in an effort to log some miles before kicking into gear over the weekend and finishing by noon Monday. (Keene students are on vacation this week.)

Barry explained that after years of training, he can run long distances and wake up the next day without too much soreness — though that was more difficult Sunday and Monday, he acknowledged.

Satan’s Sidewalk differed substantially from other ultra-marathons, Barry said, largely because he had total control over his schedule. He estimated that he was active for about 40 hours and spent 36 of them on the road.

“Basically if I wasn’t sleeping, aside from a few breaks, I was running,” he said.

He spent some of the other waking hours eating a diet that included cheese quesadillas, avocado wraps, cookies and the occasional slice of pizza, in addition to water and Coca-Cola, plus his post-workout favorite: pickles.

BURCS is donating the Satan’s Sidewalk registration fees to Moments House, a Dalton, Mass., nonprofit that provides support and healing services to cancer patients, and Barry also used the challenge to highlight another cause. Noting that his running feats typically garner interest from friends on social media, he encouraged Facebook followers to contribute to Pedaling for Prevention, a fundraiser to generate awareness and resources for suicide prevention, which two Keene High students organized last year. (The students, both of whom Barry has taught, planned to bike across the country last summer for the fundraiser but postponed their trip to this summer due to the pandemic.)

The Page Street loop, Barry said, was a familiar one because it is where he typically walks his family’s dogs.

In fact, the dogs — Oscar and Rex — joined him for a portion of Satan’s Sidewalk. So did his daughter, Clara, 7, who ran some of the early laps and joined him for the final one.

Other local runners also kept him company, including a couple of friends training for their own attempts at Satan’s Sidewalk, which participants can try any time in February. (Noting the clear weather over the weekend, Barry said a friend in central Vermont did the challenge earlier this month during a stretch of sub-zero temperatures.)

Barry said he began noticing the “patterns of the neighborhood” after a while, like who walks their dogs frequently, but added that he also zoned out for stretches and went “on autopilot, in a meditative way.”

“It went from being one of these events where it’s not fun while you do it but it’s fun after, to, ‘You know … it’s actually kind of fun now,’ ” he said.

He called it quits at 10:30 a.m. Monday, when he hit 150 miles.

Several hours later, Barry said he was feeling better than expected. He was looking forward to a couple days off and spending some time with his family.

Then, a return to training, with an eye toward the Vermont 100, which Barry hopes will proceed as scheduled in July.

“Hopefully, things can resume [in the] summer and fall,” he said. “No matter what, I’ll probably get up into the White Mountains and do some runs up there.”

Caleb Symons can be reached at 352-1234, extension 1420, Follow him on Twitter @CalebSymonsKS.