Taking Endurance to the Edge

It’s one thing to plan a long bike ride, say 100 miles. Then there are those who push themselves to ride maybe 100 miles each day over a few days. And then there’s the guy who says, out loud, ‘Hey, let’s ride 430 miles and not sleep until it’s done.’”

That’s what Flanders resident Walter Olsen, 56, said to his cycling friends a few years ago, probably during one of the many century rides they have done together. The idea became a reality last August when he and a group of friends set out early in the day from a point just south of the Big Duck in Flanders to ride the entire perimeter of Long Island. In the saddle for 26 hours and 17 minutes, with stop time, the two cyclists who finished the entire distance, without sleep, were at it for 37 hours, pedaling for a total of 463 miles.

“The whole goal was to not sleep,” said Olsen, a guidance counselor with the Three Village School District. And although they lay down on a bench near LaGuardia Airport, no one could fall asleep, even after what most would consider a very long bike ride.

“It sort of evolved,” said Olsen about the genesis of the ride. “I did my first century with Andy Drake,” referring to a 100-mile trail ride traversing the Paumonak Path they did together in 2021. After that, “I realized I can ride for a long time.”

Once he got a road bike, it was with Drake that he rode to Manhattan (and back) during the COVID shutdown. “We knew there would be no one on the road. It was eerie,” he said of riding the avenues of the city without a car in sight.

“I did a couple 200-mile rides that were just fun,” he said. And then he started to think “how much can I take, how far can I go?” and the idea for the perimeter ride started to percolate.

The inaugural perimeter ride was actually in 2023. Despite starting out with the greatest intention of doing so, they did not circumnavigate the entire island but still put in a grueling 320 miles before succumbing to pain and fatigue.

The first time “we did the city part first,” said Olsen, with the group riding from Flanders, along the North Shore, to Queens, to the southern shore. “It was so slow, with a lot of climbing in the beginning. We thought it was a good idea to get the climbing done first,” he added, but that turned out to be a mistake. The riders were pretty much shot by the time they reached Flanders, but did a final push to Sapaponack.

“I was struggling with a neck problem. I just couldn’t take it any more,” recalled Olsen, “and then Roy rode up next to me and said, ‘Walter, I just fell asleep on my bike.” They knew then it was time to pack it in and regroup for next year.

With the first, failed, ride held in June, Olsen acknowledged that by doing the challenge early in the cycling season they just weren’t ready for the demands of a ride of that duration and the hills that pulled all the reserves from their muscles early in the ride.

“I picked June so we’d have a long day of light. But we weren’t ready, I didn’t have enough endurance miles, ” he said, and moved it this year to August, giving the cyclists two extra months to build miles. The drawback to doing it later in the year is that it results in more miles in the dark, but everyone was in much better shape heading out for the long haul. To train for the perimeter ride, Olsen did a 100-mile ride every weekend in July and the last weekend of the month he did a 200-mile ride. Chavez, the guy who fell asleep on his bike last year, joined him for the 200-mile training ride, as did local cycling legend Loretta Krivickiene.

For the second try at the ride, Thomas Houghton, a 33-year-old Calverton resident who is the director of municipal work and an engineer for the Town of Southampton, tweaked the route so that the cyclists would arrive in the city at night. Arriving in Brooklyn in the daytime last year was “a disaster” said Olsen. The traffic made it slow going, not to mention more dangerous.

It was Houghton’s idea to switch to a clockwise route. Although it added some hairy left turns, by riding all of the South Fork and Shelter Island, and hugging the south shore, they arrived in the city after dark. With no cars on the roads, for Olsen it brought back that feeling he had when he rode the streets of Manhattan during COVID.

“It was pretty lonely. I was shocked. It was a Saturday night and Brooklyn and Queens were quiet” said Olsen.

Despite the realization that the city actually does go to sleep, it was this part of the ride that Olsen describes as the most beautiful.

“When we hit the Brooklyn Bridge Park, the night views over to Manhattan were amazing. All of us had ridden through here more than once during the day but this was our first time at night. Going under the Verrazano at night was also very cool, said Olsen. Plus, it was “odd to be at LaGuardia with no planes coming or going. I never knew that they stopped flying at 1 or 2 a.m.” Not so beautiful, he noted, were the amount of rats along that stretch on the East River.

Houghton, although the architect of the city-at-night route, did not get to see it. Roiling stomach issues forced him to bail after 165 miles as the group rolled into Eastport.

Antonio Nieto hit the wall — an athlete’s expression for being so physically tired that you cannot continue — on the second day. He had been awake at that point for more than 24 hours with probably about 20 of them in the saddle. Fatigue got the best of him while riding through Oyster Bay and he hopped in an Uber. To his friends’ amazement, there he was sitting on the side of the road 40 miles later, in Stony Brook, having slept in the Uber, waiting to rejoin the group, and he finished the ride.

“Anyone else would have Ubered home. It was just incredible” to see him there, said Olsen.

To his credit, Houghton brought his rested legs and recovered stomach out the second day, meeting the crew in Shoreham and finishing the last 100 miles of the route. He said that he took those last miles at the front to help block some of the wind from the cyclists who had been pedaling all through the night.

Roy Chavez, one of the original group to start the perimeter ride who did the entire distance, is no stranger to endurance rides having completed many in the last 10 years, he said. And leading up to the August perimeter ride, he had already completed the Unbound gravel ride in Kansas, which is so demanding that it attracts pro cyclists from around the world.

A 46-year-old resident of Hampton Bays, who works as a construction manager, Chavez wrote in a Strava post after the ride, “So many awesome moments happen in these crazy adventures that at the time they are happening you don’t realize how meaningful all the memories [are] and [how the] flashbacks shape your thoughts for days, weeks and eventually years after.”

The last 30 miles were tough for Olsen. Besides saddle sores, one foot was “hot” and at times he could not use it to turn the crank. He nearly dropped out in Greenport but his friends wouldn’t hear of it. With 20 miles to go, again off the bike because of foot pain, Olson spied cyclist friends Steve Dorn and Andy Drake riding up the road. Drake was expected to turn up for the home stretch but not Dorn.

“Steve and I have ridden thousands of miles together and I’m sure what he was looking at with me sitting on the ground was nothing he had ever seen before. But in typical Steve fashion, the first thing he says to me is, ‘Get up, bitch, we gotta get home!’ I can’t explain what happened to me next, but I do know that I was overwhelmed at the amount of support that was around me at that moment. No one knew it then, so they’ll know now but there were tears behind my sunglasses,” wrote Olsen on his Strava page.

In the end, Olsen and Chavez completed the entire perimeter ride. Of those who didn’t complete the entire distance, besides Houghton, the guy with the stomach issue; Nieto, the guy who hopped an Uber for 40 miles, clocked 422 miles; Dave Cooke, 185; Jason Lee, 175; Joe Mordarski, 173; Jose Pena, 145, all riding on day one; Scotty Plushau, 80 the first day and 20 the second; Steve Dorn, 20 miles; and Andy Drake, 20 miles, were along on parts of the ride to help see their friends through the incredible challenge.

Both Olsen and Houghton described how they were filled with emotion after having finished the ride, and are already talking about next year, with Houghton adding that they have to work on beating their finish time.

“I highly recommend getting out there and pushing your limits to the max; you’ll be surprised how much more you can actually accomplish than you expected. The feelings of fulfillment make it all sooo worth at the end,” said Chavez.

Reminded of the question he posed to himself while thinking about the ride — how much can I take? — Olsen said this was probably it. “After 430 miles, I felt like an old car.”