By jake goldman

The author (left) and Tim, his friend of 15 years, lost on an outing in Downsville, NY

This piece is part our "I Did It!" series, a collection of first-person essays celebrating outlandish means and wild achievements. Submit your own story by emailing The Airship’s editor at

We hit the trail around 9 A.M., already three hours behind schedule. The air on this July morning was thick and still, the grinding drone of cicadas crowding the soundscape. The trail was the Farmington Canal Trail, a non-motorized, multi-use path that stretches from New Haven, Connecticut to Northampton, Massachusetts. I'd been living in New Haven for close to a year, and ever since I'd been there, the trail called to me. I can't exactly put my finger on why. It's not as if riding the trail's length is some monumental feat. Eighty-four miles in one clip, while impressive, isn't exactly jawdropping.

But my friend Tim was game. We've been friends for nearly 15 years and try to cram in an assortment of outdoor excursions each summer. By the end, we generally annoy the hell out of each other and end up not speaking for a few days. The annoyances tend to come from our shared disposition towards not planning a goddamn thing. It's not that the lack of forethought comes from of a certain ideology, it's more a combination of laziness and an unwillingness to admit that we don't actually know what the fuck we're doing. Previous plan-less excursions resulted in getting lost several times in the woods with a lack of water and the sun sinking behind us, as well as me falling about 11 feet from an ATV and splitting my knee wide open.

Here is how we planned for an 84-mile bike trip: we bought eight Clif bars, a little granola, some bike shorts and three spare tire tubes. Shoved those items, plus a Camelbak pouch of water, into tiny backpacks. Dusted off an old map of the canal trail. Emailed a guy named Norm, president of the Farmington Canal Rail-to-Trail Association. Norm said: "Bring a lot of water!" Well, well. According to Norm, we were ahead of the game.

An entryway to the Farmington Canal Trail near the Hamden-New Haven border

Back to the trail: We made good time through New Haven and Hamden, the first two uninterrupted segments. The trail is wide and tree covered, with slats of sunshine coming through here and there. The scenery changes rapidly from the desolate New Haven projects of Newhallville to Sleeping Giant, a gorgeous mountain that looks exactly like a man lying on his back.

In Cheshire, the trail comes to a halt for the first time, running right into a two-lane road. As we'd later learn, this happens in three or four other areas along the way, something the map I had doesn't exactly account for. We fiddled around with Tim's iPhone, but couldn't find anything concrete as far as reconnecting with the trail. On the shoulder of the road, I spotted two thinly spraypainted arrows, one green and one white. I looked at the less-than-helpful trail map in my hands, noticing the primary color scheme was green and white. This was somehow a good enough connection for us both. We followed the arrows.

A bridge on the trail nearby the Hamden-Cheshire border

Said arrows took us through sizable hills and tony Cheshire and Southington neighborhoods, rows of gigantic colonials with oversized garages and sprawling pristine lawns. The wind picked up a little here, and 25 miles in, we felt pretty good getting misted by sprinklers.

In Avon, we came to a sign: "Farmington River Trail," which gave way to a paved path. But the word “river” was throwing me off. The river wasn't the canal. Or was it? Fuck. This is where some research would have helped. And then there were the green arrows. They'd been leading us so well. I'd convinced myself they were somehow here just for us — mystical messages maybe from Norm, showing us the way. The compass Tim had told us we were headed Northwest, where we wanted to be. I voted for arrows, which looped to the left of the trail up a hill. Tim, frustrated, took off ahead of me. I wasn't in the best shape and chose to walk my bike up.

The only remaining original canal lock in Cheshire; the lock house to the right is still functional, and opens its doors as a museum once a month.

At the hill's crest, the road split in two and I couldn't see Tim. I reached for my phone, but it wasn't there. I realized Tim had it in his backpack, along with the extra water and our weed. After slapping my forehead for a bit, wishing I'd done a better job planning or at least asking Norm some more specifics, I continued on with the arrows, hoping Tim had done the same.

Turns out the arrows weren't some sort of mystical, secret message, as they took me right onto an onramp. I skidded to a stop and turned around. A few miles later, I came to a farm stand and ask to borrow a cellphone from the kindly man underneath a tent hawking pies and jams. He heard the message I left for Tim and said: "Northampton? Why in the heck would you want to ride your bike there?" I laughed nervously and bought a jar of jam.

Eventually, I reconnected with the trail, just before hitting the Massachusetts border in Southwick. I stopped there at a cafe that looked like a barn. They had shitty turkey sandwiches and lukewarm coffee, but also a porch with rocking chairs. I sat out there, chewing on dry turkey in the late afternoon, watching families glide by on bikes, cursing to myself. Inside the cafe, the very bored staff gladly filled my Camelbak in the slop sink. They asked me: "Why do you want to ride your bike that far?" I just laughed and bought two really big cookies.

I sped, sweat soaked into Westfield. The trail there just sort of ended and gave way to a ditch. I stopped and screamed FUCK!s into the forest. I was punching my handlebars when an older man on a beat up road-bike stopped me and asked me what was wrong. I told him I had no idea where my friend was and that I was out of water, and he just started rubbing my shoulders. I let it happen. It was weird. He went to his rucksack to fish out a phone, still keeping a hand on my right shoulder. Then, out of nowhere, Tim appeared. He looked pissed, but handed me a Gatorade. I introduced him to my new pal who said he'd lead us to Route 10, which we could take all the way to Northampton.

Route 10 through Western Massachusetts is halfway between a rural road and suburban sprawl. Cars zipped past us pushing 60. We hugged the shoulder hard. We passed by vacant motels and pool supply stores, F-150s barreling beside us. This wasn't part of the fantasy. Where were the waterfalls and the rare birds?

In Northampton, we stopped for mediocre Mexican food. When we were finished, we hopped back on our bikes and headed for a KOA (Kampground of America) cabin we’d rented in Easthampton. On the ride there, many miles south of Northampton, the skies opened and the deluge came, pissing on us for an hour. Inside the main KOA lodge, the married co-owners handed us keys and asked: “Tell us again why you rode all the way here from Connecticut?” I laughed, bought a Charleston Chew and asked for some towels.

In the morning, over instant coffee and stale granola, Tim tried to find a better route back home. We were southeast of Northampton and needed to continue in that direction. Tim found a bike-map-specific phone app. Someone from Portland, Oregon made it. Seemed reasonable enough.

On the way back, we came to a rocky portage road. According to the app, the road was the way to go, despite its clear inaccessibility. Still, we'd already come three miles, and the compass still pointed south, so we hoisted our bikes onto our shoulders and walked. After a mile, we came to a rusted metal gate. There was barbed wire around the top. No Trespassing. It looked like a driveway to a large private estate. Surely, there'd be shotguns, probably dogs. To the right was a small trail, some stamped down branches and leaves to the left of the gate leading to a shallow river. We decided to take it, not wanting to admit we'd fucked up once again.

We walked south along the river. It wasn’t actually a trail —& it was a forest. We were walking through a forest now. Tim walked through an entire briar patch, and when he stepped out, his shins were dripping with blood. I worried about poison ivy and ticks and death.

After three hours, we came to a clearing in someone’s backyard. There was a swingset and freshly mowed grass and station wagons in the driveway. We were howling and hugging. Tim was still bleeding.

Then, the crashes came: We rode along the gravelly shoulder of Route 10 at this point, abandoning any hope of reconnecting with the trail. I wiped out in Avon, flying into a tangle of branches. In Plainville on a main road, I flew too fast through a red light, slammed on the brakes and skidded half a foot on my ass. In Southington, I crashed again and fell into a ditch.

“I think your body is telling you something,” Tim said.

“I think I hate this,” I said.

Thankfully, a friend from New Haven was free and came to rescue us. We sat in silence on a long lawn, watching hawks and turkey vultures trace the sky.

By the time I got home, my extremities were bright red. I itched like crazy. When I went to see my physician about it a few days later, he just scrunched his nose looking at me with his little light and stethoscope.

"Didn't you know what you were getting into?" he asked.

I laughed and snatched the prescription for Prednisone out of his hands.

Jake Goldman is a writer. He lives in Providence, Rhode Island, where he’s probably drinking coffee milk.

Have a first-person essay celebrating your own outlandish means and wild achievements? Submit it to our "I Did It!" series by emailing

(Image credits: from Lauren Kirchner; all others from author)

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