Trail Mavens


Skill-based camping and backpacking trips for groups of extraordinary women. Ready to build fires, read maps, pitch tents, hike, laugh, and drink wine around the campfire? Join one of our weekend adventures.

Introducing Jessica Mastors

Name: Jessica Mastors
Hometown: Exeter, Rhode Island
Superpower: Fun-making
Favorite Trail Mavens lesson to teach: Fire-building

How did you develop your prowess as an outdoorswoman? 
I grew up in the woods and spent a week every summer at an environmental education camp, trawling my ponding net through the muck in search of diving beetles and tadpoles and dissecting the occasional owl pellet.

At fifteen I spent three weeks in Maine backpacking and rock climbing with Outward Bound, which taught me that hiking stops being terrible after about two weeks, and that your hair starts to clean itself (!) after about the same about of time. It was in the final days of that trip, scrambling south through the field of boulders known as Mahoosuc Notch, that we encountered an extremely thin and haggard-looking man walking very, very slowly in the opposite direction. He told us he’d walked all the way from Georgia, and our little minds were blown.

Ten years later, I would find myself following that skeletal man’s footsteps for more than 2,000 miles, on the Appalachian Trail thru-hike that would change my life. I guess you learn a little bit about living outside when you do nothing else for 6 months straight.

How do you spend your time when you're not leading Trail Mavens adventures?
Telling stories, reading stories, writing stories, editing stories, helping others unpack the magic of storytelling, generally playing with words and delivery and imagination, puzzling out how to build an online business, admiring fierce lady leaders and anyone who has the courage to live a life that is true to themselves, fantasizing about biking south to Chile and hiking the PCT and walking across Spain and building a cabin on the sweet piece of land I’m saving up for, cooking food, drinking wine, making love, occasionally dog-sitting for a 138 pound bullmastiff named Solo.

What do you love about leading Trail Mavens trips? 
I love everything about leading wilderness trips, but Trail Mavens trips are truly a special breed. I love being surrounded by daring women; ladies who are willing to take a risk on themselves and on a new, uncertain experience, just to see how it makes them grow. I love sitting around the fire listening to stories of adventure, fear, courage and revelation. I love it when a woman says she can’t, and then surprises herself when she does.

Tell us your go-to story of a personal outdoor adventure experience.
They say that 87% of people who set out to thru-hike the AT will quit before they make it halfway. Once you get halfway, barring a true emergency, you’re pretty much guaranteed to finish.

Of those that quit, there are three types of quitters: those who quit right away, because it is NOT what they were expecting; those who quit when they get their first injury; and those who endure their first injury and press on, only to quit when they get hurt a SECOND time, because the novelty of suffering has worn off.

It’s not that it hurts -- it’s that the hurt is no longer new.

The real rollercoaster isn’t the ups and downs in elevation. The physical challenge is real, but it’s the psychological challenge that gets to you. It gets in your head, hiking one mountain after another after another, only to arrive at the base of ANOTHER MOUNTAIN, when you’ve already done the work of climbing so many. (Entrepreneurs can probably relate to this.)

Then you get to town, where you encounter townspeople who wonder why you smell so bad and why you’re carrying everything on your back. When you confess that you are hiking the AT, they tend to ask the same 6 or 7 questions (where does it start? Where do you get food? How many miles a day do you hike?), and then they get to end of their questions and say:

“Well, I could never do that.”

At first you think it’s cool, because they’re trying to say, “Good for you, that’s tough!” But when you hear it a dozen and then two dozen times, suddenly you just want to SHAKE them and say:

“IT’S NOT THAT YOU CAN’T. It’s that you just don’t WANT to. Hiking is walking, and you don’t want to take 6 months to walk across the country, and that’s OK! You have other things to do, a career or a family or a penchant for bathing regularly. Let’s be clear: it’s not an issue of capacity; it’s an issue of priorities. And the thing about priorities is that you can only have so many. So stop telling yourself this limiting story about what’s possible that simply isn’t true.”

I spent a lot of time walking in the woods, putting one foot in front of the other, thinking about the stories people tell themselves about what’s possible in life. Whenever I thought about quitting, I asked myself: “How bad do you want it?”

And the answer was always that I wanted it really bad.

When I made it to Katahdin and gazed out at the vast green country I had just crossed by foot, I thought: This is how “impossible” things become possible. By breaking it down into 5 million steps, and wanting it bad enough to take just one more.

If you were a piece of gear, what would you be, and why?
I started the AT without hiking poles, thinking (as the young and reckless are prone to thinking) that I wouldn't need them.

By the time I arrived at Neels Gap, where some smart and enterprising person had established an outfitter in the middle of nowhere precisely for naive and cavalier people like me, my knee was the size of a cantaloupe.

While I surveyed the goods and weighed the pros (support and relief for my screaming knee) against the cons ($200 price tag), a portly man came up to ask if he could help. I explained the dilemma and asked if a $12 knee brace would do the trick.

He took one look at my knee and motioned for me to wait while he disappeared in back.

When he returned, he was holding a pair of battered and slightly bent Leki poles, each bearing a strip of carefully applied duct tape that I would later use in waterproofing emergencies.

"These are nothing special," he said, "and they probably won't last you long. But they're better than nothing." After adjusting them to my height, Baltimore Jack sent me on my way without asking for a dime.

This was my first experience of Trail Magic, whereby complete strangers, known as Trail Angels, go out of their way to assist and comfort you. And those “nothing special” poles brought me all the way to Katahdin.

To me, they are a reminder that you don’t have to (and indeed shouldn’t try to) do everything by yourself; that the world is generally a kind place; that magic is real; and that sometimes the best thing to do is ask for help, and accept (with gratitude) the gifts that come to you.

Jessica Mastors is a story coach and strategist, writer and wordsmith, free thinker and troublemaker. She loves mountains, elephants, metaphors, and chocolate with fruit inside. If you're in the Bay area, come learn how to make magic with your stories at her next Story Magic Playshop or sign up for one of her Trail Mavens trips to Lake Tahoe, Hendy Woods or Yosemite.

Want to adventure with Jess and our other amazing guides?
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