John Hess has earned the reputation for being a completionist — and with good reason. When he takes on a challenge, he sees it through, often doing more than is expected. This October, for example, he not only finished Greenbelt’s Go-Getter Trails Challenge by hiking all 55 listed properties, he added five more for good measure. Two years ago, he also completed Greenbelt’s inaugural Go-Getter Challenge (adding extra properties then as well) and has finished a similar hiking event hosted by The Andover Village Improvement Society (AVIS), where he has served as a trustee for more than 18 years. He has also tackled the entire 230-mile Bay Circuit Trail and the 30-mile Mystic Link trail from Andover to the USS Constitution.
While he has always been an outdoor enthusiast, John notes that much of his hiking has taken place since his retirement after a lengthy career in healthcare administration. He understands that most people don’t have the leisure time needed to pursue such ambitious hiking goals. “What’s great about the Go-Getter Challenge is that even if you only visit a handful of properties, you’re still out there participating,” he says. “You’re spending time in nature and discovering new places. Anyone, no matter how much time they have, can get involved.”
To date, nearly 300 people have signed up for the Go-Getter Trails Challenge, which invites participants to explore Greenbelt’s protected properties across the region. Running through May 30, 2026, the challenge is free, open to individuals and teams, and suited to every pace. Whether you prefer to hike, bike, run, stroll, snowshoe, or simply wander, it’s the perfect excuse to get outside. New sign-ups are always welcome.
As part of his involvement with AVIS, John is collaborating with the Andover Trails Committee on the latest edition of the townwide Andover Trails Guide. His connection to Greenbelt began in 2018 when AVIS partnered with us to co-lead walks in the Merrimack Valley, and he’s been a friend and member ever since.
As for being called a completionist, John admits the description fits, but says he doesn’t go to extremes. “I do everything in small chunks, two to four miles at a time,” he says. “I enjoy visiting familiar properties, discovering new ones, and getting outside to explore at my own pace. The Go-Getter Challenge just adds a bit of extra motivation.”