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The Subversive Joy of Hiking Through Private Golf Courses

Golf courses have long been islands of exclusivity and privilege in America. But one avid urban explorer says that, when in the right hands, they can also be a tranquil oasis among big-city madness

Eight years ago, Miles Howard, a journalist and avid outdoorsman based in Boston, was stuck in a quarter-life crisis and feeling restless. Seeking a challenge that would stir up his motivation, he planned a winter urban hiking trek across the state, charting a path along what he assumed would be calm backroads with decent pedestrian access

He assumed wrong — the path landed him on a series of awkward highways without sidewalks, leaving him at the mercy of passing cars. As he approached the town of Hudson, about an hour’s drive west of Boston, Howard realized he needed an out. Through a line of trees in the distance, he saw it: A sunny stretch of green grass that seemed to lead directly to his next landmark. Howard forged a path from the road to the boundary of the meadow, only realizing at the last minute that the property was actually Charter Oak Country Club, closed off for the winter season. He peered around, saw nobody, and slipped onto the grounds. 

“After about 20 minutes of walking through all the holes and sand traps, I realized that I was enjoying myself more than I had for the past few days of hiking areas that weren’t really designed for pedestrians at all,” he tells me. “It was partly about the peace and quiet of the course, but I also enjoyed the realization that I had leveraged this space for something that was completely against the intended design of the whole thing.”  

Golf courses have long been divisive in the context of communities, courting hard questions about exclusivity, access and sustainability. These courses usually represent some of the biggest, most pristine stretches of green space in many major urban areas, making the history of golf courses all the more problematic. It was one of the final American frontiers in the fight to break racial and gender-based discrimination, and cultural cornerstones like the Masters still struggle to confront its recent sins. 

That’s not to mention the debate around the environmental impact of golf courses, especially water and pesticide usage to maintain manicured fairways. Despite credible claims that responsibly managed golf courses are a net positive for the climate, calls to abolish golf courses or otherwise reform them into public parks continue to crop up. 

For Howard, being on a golf course at all was a novelty: Growing up on the “lower end of the economic ladder” meant he never thought about trying to enter a country club. And he didn’t really trek onto a golf course after that winter in 2014, until the pandemic hit in 2020 and left him stir-crazy in Boston, once more. 

Again in winter, he decided to wander from a pedestrian path at Franklin Park onto the hilly city-managed golf course that sprawls through the heart of the site. His experiences recently inspired a post for his newsletter, Mind the Moss, in which he urges that we all “take back golf courses” by trespassing on them in good faith, with no other intentions than enjoying the scenery and the subversion of daring to walk on green space designed for slapping a tiny white ball around. 

It’s not just an activity for the winter, either, although seasonal closures make it easier to not get caught. Many courses are so vast that there’s a lot of underused green space at any given time, even with golfers playing through them, he notes. That means plenty of opportunity to explore the wildlife and natural flora of the grounds that line the green, which research has found can be hubs of surprising biodiversity in urban regions. 

And while it’s likely that hiking through an active golf course will attract some attention, Howard suggests that this adds cheeky humor to the whole journey: “I am not necessarily treading on their rights and what they paid for, which is the right to play golf. I’m not doing that or taking that from them. I just happen to be a part of their environment,” he says. “There are layers to this subversion that I find very entertaining.” 

If there is a confrontation with a golfer or a groundskeeper, the easiest thing to do is just feign like you got lost and were on a public path; you could also keep a cold beer or two in your backpack as a peace offering. But as Howard points out, there’s not much inherent harm for anyone to get angry at; the impact of walking across the course is less than that of anyone playing on it, certainly. Instead, it’s a soft form of subversion — a reminder that breaking the rules can both be fun and send a message about our right to wander, even in the face of privatization. 

“One of the most liberating things you embrace with urban hiking, as opposed to the normal kind of more rugged hiking, is that you can do it right from your door, literally. It’s not an escape in the sense of traveling to a distant destination, but as a foot journey into an environment with a perspective that’s unfamiliar and disarming. In some ways, it’s one of the most accessible forms of hiking,” he says. 

For him, the whole experiment recalls a sketch from the first Jackass film, in which Johnny Knoxville and Co. sneak onto a golf course, hide in the rough and startle golfers by honking an air horn as they swing. It’s a childish little bit that’s hilarious primarily because of the reaction from the golfers, who bellow and stomp with an existential rage because their game has been interrupted. “I felt like they were really getting something deeply elemental and human with that sketch right there, between the absurdity of golf culture and the exclusivity of it all,” he says. 

Trekking across your local golf course isn’t quite that confrontational, of course — but the spirit of the act remains the same. Golf courses can be fun for non-golfers, too, if you’re willing to push expectations and step onto the green.