Andy Montgomery: Trail by Trail in San Francisco

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Andy Montgomery, a trail runner based in San Francisco, California, loves when his more road-focused running friends visit him in the Bay Area. More specifically, he loves witnessing the moment when they realize why he has such a passion for the trails.

“People like to ask, ‘Why do you want to drive all the way out of the city just for a run?’ And part of what can be intimidating about the trails is that there are so many, and it can be confusing,” Montgomery, 37, says. “But it’s just one of those things where you get out there and you can see it click—they just say, oh, this is just amazing, I get it!’

“You get all these beautiful views, and there’s just something about running the trails,” he continues. “It’s usually a more difficult run, but you don’t notice it because of the change in the environment and the natural beauty. All of these things just really come together.”

Montgomery’s own interest in trail running was piqued, not surprisingly, in the trail running mecca of Boulder, where he lived for several years before moving to San Francisco. Prior to that, he’d spent time in several outdoorsy cities in the Southeast, including Chattanooga, though he was almost exclusively a road runner then.

In 2010, he moved to Boulder, where he fell in with a group of trail runners and discovered a whole new world of running. “I’ve noticed there are a lot of people with a similar experience—once you start running trails, it’s hard to go back to the road,” he says.

Taking in the view from the Amansa Back Trail in Moab, Utah.
Taking in the view from the Amansa Back Trail in Moab, Utah. Megan Coatley

Inspired by Boulder’s trail running community and spectacular trails, Montgomery, who usually used to run no more than six miles at a time, began transitioning to longer distances, and his first half marathon was on the trail.

“One of the nice things about the trail race culture is that it’s much less about speed,” he says. “I knew that if I couldn’t run the whole thing, I could walk or speed hike portions of it, and it would be a nice beautiful day regardless. It worked out really well. I had a really good first race and felt a lot better than I expected to.”

Montgomery also discovered that his new passion was a great way to explore much more of Colorado, in a much quicker time frame. “If I was backpacking, it would take me three days to see all this ground,” he says. “But with trail running, we’d cover 20 miles in one morning, seeing places that most people don’t get to go to. You just get to see so much natural beauty.”

After moving to San Francisco in early 2013 for a job with a startup technology firm, Montgomery was thrilled to discover a similarly strong trail running community in the Bay Area. On Saturdays, he participates often in the popular group runs with the Mill Valley-based San Francisco Running Company. Though he’s now familiar with most of the trails in the Marin Headlands, his favorite route is still to the top of 2,571-foot Mt. Tam, which he often ran when he first moved to San Francisco.

One of Montgomery's favorite places to run in the Bay Area is Mount Tam.
One of Montgomery's favorite places to run in the Bay Area is Mount Tam. Miguel Vieira

On weekdays, Montgomery takes to the city’s urban trails, including the ascents to Mount Sutro and the approximately 8-mile route from his apartment in the Haight-Ashbury neighborhood through Golden Gate Park to Ocean Beach.

“I can stay on trails the whole way there and back, and it's always nice to see the coast midway through your run, even if it’s cold and foggy,” he says. “We’re really lucky in San Francisco that there are so many urban trails and so much green space, and if you like running hills, you’ve certainly got that here as well."

Since moving to the Bay Area, Montgomery has continued to up his mileage and has moved on to ultra distances. This year alone, he’s cranked out three 50Ks—in Moab, Utah (“I just love that part of the country—it feels like you’re on another planet,” he says), Squamish, British Columbia, and Cool, California (yes, that's the name of a town).

Next up on the calendar: Montgomery’s first 50-miler, the North Face Endurance Challenge in December, which winds through the Marin headlands.

Josiah Roe

Like many ultra runners, Montgomery never could have imagined himself tackling such distances even just a few years ago. “It was a little intimidating at first, but when you start being around these people doing these crazy distances, you start to think less and less that they are crazy,” he says. “It’s just one of those psychological shifts in the whole trailing community – once you get into that training, things seem less and less crazy.”

To some outsiders, however, Montgomery’s passion still elicits some head-scratching. “My family still thinks I’m crazy,” he says with a laugh. “They’re training for 5Ks, which is also great. But you lose perspective when you spend all of your time with people who are training for 50- and 100- mile races.”

Montgomery is mulling over the idea of a 100-miler, partially inspired by his time volunteering at Western States this year and seeing finishers come over the finish line. Although he wants to see how the 50-miler goes first. For now, though, he's just savoring his time on the trails. "There's no quick answer to why I’m drawn to running eight to nine hours at a time, but what I’ve been coming to recently is that I just get a lot of joy while running in the mountains," he says. "It has this experience like you’re on a journey. And I’ve begun to find that I get a lot of joy out of that—something I haven't had elsewhere in my life."

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