Patchwork

How the promise of a prize inspires us to do crazy things outdoors

In case you haven’t heard yet, something BIG has been cooking in Boston lately. The Walking City Trails network of cross-town urban hiking trails, which I founded in 2022, is just a few weeks away from welcoming a new addition: a trail around Boston’s leafy and salty perimeter that will be somewhere between 80 to 100 miles long! Cambridge Day published the scoop the other week, and at the moment, a small of crew of us are in the process of scouting, mapping, and photographing the final sections of the trail, which will officially launch on June 6th (AKA, National Trails Day) at BostonTrails.org.

Naturally, the question of how many people will actually hike 80 to 100 miles around the City of Boston border has come up. But I have an ace up my sleeve; an incentive that could be the difference between “sounds neat, in theory” and “let’s fucking go!”

I am going to offer a free, commemorative patch to anyone who completes the trail.

Now this might sound absurd—the idea that people would spend days or even weeks out in the sticks, putting distance on their soles and micro-tears in their calves, just so they can claim a 3-inch woven patch with the name and logo of the trail they’ve hiked. But for some reason, which I don’t pretend to understand, the allure of a prize, grand or pithy, can inspire some truly unhinged ventures in the outdoors. If you traverse the 365-mile Erie Canalway trail across upstate New York and record your miles using a special logbook from the Erie Canalway National Heritage Corridor, you can receive a finisher’s kit that includes a pennant, a car magnet, and….drum roll, please.…a sticker!

Appalachian Mountain Club

Or consider the Bay Circuit Trail; a C-shaped trail through the woods and wetlands of Greater Boston that stretches for 230 miles from Newburyport to Duxbury. In 2017, the Appalachian Mountain Club’s director of operations for the Bay Circuit Trail, Kristen Sykes, created a program in which anyone who completes the trail can claim a nifty AMC pin. I think it’s safe to say that these programs would not continue running if people were not finishing the trails and claiming the prizes with some regularity. And I can attest to that because shortly after the launch of Boston’s Walking City Trail (the namesake 27-mile trail that started the network), I launched a similar program through which you can receive a free “WCT” trail patch after completing the trail. The number of people who have claimed the patch is modest enough that I’m not worried about cheating—most of these programs run on the honor system—but the claims hit my inbox frequently enough in spring, summer, and fall that I’m pretty much covinced that the power of patchwork can help activate any trail or outdoors-based challenge.

It’s a fascinating psychological paradox—doing so much for so little—and I wonder if some of this is rooted in nostalgia for a bygone era when opportunities to claim free shit were ubiquitous in American life. You could find them on a box of cereal. I fondly remember rifling through boxes of Berry Berry Kix when they carried X-Men trading cards, in search of the elusive Professor X. I can also recall how the arrival of a box of Red Rose Tea in our house meant adding a new porcelain figurine to our collection. Each box included one of these little creatures, which were crafted by the legendary English pottery manufacturer Wade Ceramics. You could even save up the tiny comic strips from rolls of Bazooka Joe chewing gum, mail them to the Bazooka Joe HQ, and claim a prize comensurate with the number of comics you amassed; like X-ray glasses or a whoopee cushion. Rising manufacturing costs, and the widening realization that marketing molar-rotting foods to kids with prizes might be unethical, killed the party.
But those of us who lived that era know: It was a hell of a party, and worth the fillings.

You might say that the growth of prizes for walking, hiking, and outoor adventuring is an evolution of this lost tradition—prizes in the service of activities that are great for our health and happiness. Nonetheless, I still find myself surprised by just how far a number of people are willing to go, in pursuit of their prize. Some years ago, a family of New Hampshire hikers named Trish, Alex, and Sage put together a list of seriously exposed, vertigo-inducing hikes in the Granite State that they called The Terrifying 25. It didn’t take long for New England hiking communities to find this list and treat it like a quest. And for the finishers, a special Terrifying 25 patch was created. list. But having done a handful of the hikes on the Terrifying 25 list—most traumatically, the Six Husbands Trail up Mount Jefferson, which includes a dismount from the top of a tall wooden ladder to a slick, sloped cliff that left me shuddering—I’m not sure if the luster of the patch would have gotten me through all 25 of these hikes. Even Adam Hoyt, an outdoor influencer with a greater tolerance for terror, found the Six Husbands Trail freaky.

Nonetheless, there’s always someone out there waiting to empowered or enabled by a “free” prize, no matter the cost that’s actually paid in labor or exposure. Several years ago, a white-hot bagel vendor here in Boston upgraded from a farmer’s market stand to their first brick-and-mortar store. To ensure a crowd, they offered one free bagel to every customer who visited that day, until they were cleaned out. It was a windy, rainy morning in late April, still bitter enough to numb your fingers, and my friend/current housemate Katie and I decided to jog over there and leave a trail sesame seeds in our wake. We figured the bad weather would be a deterrent…and we could not have been more wrong. The line of people waiting to get into the tiny bagel shop didn’t just spill out the door. It ran the length of the block and then it wrapped around the block and disappeared from sight. There were several families with small kids and babies in line, hypnotized by the promise of a free bagel and unbothered by the likelihood of being stuck at home with runny noses the next day. Hungry as we were, Katie and I couldn’t get into the zone like that. So we went home. And we still talk about this sometimes.

Maybe you were one of those people, enduring the drenching rain so you could sink your teeth into a pillowy ring of dough that would have cost $2.50 on any other day. Perhaps you’ve done something even more reckless and inspired outside, driven by the promise of acquiring something that you can wear on your jacket or slap on the bumper of your car. If so, I’d love to hear about it. Sound off in the comments below, by all means! And even if you haven’t earned a prize for doing something challenging outdoors, I’d love to hear what you would be willing to do, and for what prize. Would an engraved butter knife be enough to get you training for the Cactus to Clouds Trail up California’s Mount San Jacinto, in which you gain more than 10,000 vertical feet in 19 miles? Could you imagine cold plunging into each of the Great Lakes in December and uploading a selfie of each plunge if it earned you a special beanie with the shape of the lakes embroidered into the hat? (I think I already know my dad’s answer.) And above all, why do you think that patches, pins, and other prizes have this effect on us?

We may never know, but we can certainly keep chasing answers, along with the prizes.