Three years out of school, working steadily as a freelance scribe, paying rent in Boston and getting used to ATM visits that weren’t accompanied by heart palpitations, I wanted an escape. Two weeks of travel somewhere exotic seemed like an ideal “treat yo’self” indulgence for finally feeling like an adult. But I wasn’t ready to plump for a ticket to any of the expensive places my Instagram friends always seem to be frequenting. Instead, my eyes were set just beyond the city limits: I decided to hike across my home state.

The perks were threefold. Massachusetts offered mountains, villages, cities and beaches. The trip would be relatively cheap. And best of all, I could plan the entire expedition on my iPhone. A smartphone safari. Between Google Maps, Airbnb, Yelp, and - if I was feeling especially outgoing - Tinder, what more could a traveler want?

I spent several excited weeks researching roads that seemed safest for strolling along, booking bedrooms in country homes and planning highly caloric dinners at restaurants with names like Barney’s Chop House. My data usage shot through the roof, but hey, I was saving money in the long run! No expensive resorts or airline fees for me. Stepping out of my front door on a raw December morning, bus ticket and backpack in hand, I felt like the progeny of Steve Jobs and Bilbo Baggins.

Five hours later, I was high in the Berkshires. It was 11 AM. I watched the bus disappear down the road, into the forest. Every tree was frozen solid, but the sound of a thousand branches creaking against the wind made me feel like I had stumbled into the film Badlands, wherein a young Martin Sheen and Sissy Spacek embark on a killing spree across the most beautiful parts of South Dakota. I pulled out my iPhone, opened Notes, and typed Watch Badlands when home. And then I began walking east.

For the first hour, I felt nothing but gratification. All I could do was gawk at the landscape and imagine how vivid those rolling charcoal-colored mountains must have looked during autumn foliage season. Then I remembered, I didn’t have to imagine at all. A few taps on my iPhone summoned images of the Berkshires during October, painted burnt orange with endless leaves. I squinted at the screen, scrolling through countless pictures with two chilled fingers.

Suddenly, it no longer felt so novel to be walking country roads in the middle of winter. I began noticing the rustle of my jacket and the 40 pounds on my back, imagining how I could have packed featherweight gear during warmer seasons. I was briefly tempted to perform a new image search for “Berkshires summer.” But then, I stumbled across something that made my heart sink. I had arrived at the first fork in the road. And from the looks of it, I wouldn’t be walking much further.

Big rigs and salt-encrusted SUVs screamed past me, a blur of metal hurtling in both directions. The road I had selected for the next six miles, a road that had looked colonial on Google Maps, was a rural highway that offered no walkable shoulder. Panicking, I whipped out the iPhone, only to find that the cold air had caused the battery to shut down. The phone left me with a pleasant little “ba-dink!” And then, I was alone.

Well, for about five minutes. As I contemplated returning to the bus stop, feeling like a real cupcake, a red Subaru Forester broke away from traffic. And before I could react, a woman with three toddlers loudly squabbling in the backseat stuck her head out the window and shouted, “You! Want a ride?”

I hesitated. Getting into that car would be a deviation from my iPhone-orchestrated planning. There was no way to “vet” this Good Samaritan, the way people appraise their Uber drivers. But the woman’s offer was a means of warm passage to unfamiliar territory. Wasn’t this why I had ventured out here in the first place? I smiled and ran towards the moving car.

We flew down the road as though fired from a rocket launcher. I zipped open my backpack and groped for my wallet, but before I could offer some gas money, my rescuer asked if I would care to plug my phone into a white cable that sprouted from the cigarette lighter.

I thought about this as a gas truck passed us on the left.

“Thanks, but it’s buried in my pack,” I lied, sitting back, heating my hands over the air vent, staring at the winter sky, and listening to the woman’s kids strangle each other.

We parted ways on a corridor of slush called Cummington Road. I was once again alone in the snowbound countryside. As I resumed walking, I became aware that my feet were sweating in their wool socks. This was a pleasing tonic to the brutal winds that chapped any inch of exposed skin. I squelched onward, quite happily. A few miles later, I found myself sniffing at trees, taking great huffs of the aroma and trying to guess the species. (Most of my wagers boiled down to some variation of “Pine.”) Slowly, I realized I was famished.

There were no restaurants or general stores in sight. The only thing I had eaten on the bus was a protein bar which offered the taste and consistency of that pulped wood filling you find inside IKEA coffee tables. That was hours ago. I had just walked 10 rolling and tumbling miles. I was ready to push a burrito into my face like a log into a sawmill. The question was, where?

Rather hopelessly, I pulled out my phone, expecting to be greeted by a black screen. But in the relative warmth of my pocket, something remarkable had happened: my iPhone had resurrected itself! Once again, I had valuable information at my fingertips: directions to dinner. And yet, I couldn’t help but wonder, if I hadn’t tucked the phone away for the car ride and the past few hours of walking, if I hadn’t dropped “off the grid” temporarily, would the phone have come back?

This was a question better pondered over fat and carbohydrates. Some quick GPS scrolling revealed a promising establishment called Listons Bar & Grill, located one mile down the road. The joint boasted a four star Yelp rating, which was all I needed to see. After a long afternoon of walking, it seemed ridiculous to agonize over the specifics of each review. Was this the best eatery in the area? Should I hold out for another hour and look for better options? Again, these are questions one shouldn’t ask on a neglected stomach.

As I set off for the restaurant, I made a solemn vow: going forward, I would think of the iPhone not as a travel buddy, but like a concealed flare-gun, only to be whipped out in times of feeling lost, hungry or hunted by animals. (Assuming that BuzzFeed had at least one listicle for surviving a bobcat mauling.) Picking up my pace, thinking of melted cheddar and unsavory characters, I slipped the phone back into my pocket.

It was 5 PM. I was far from home, and happier for it.

I won’t pretend that walking the rest of Massachusetts with my iPhone was always harmonious. The next morning, not far from Liston’s, I woke up in the cozy $20 room I had rented via Airbnb (which had likely belonged to a child, judging from the Land Before Time bedsheets), and wasted almost an hour in bed Googling carnivorous dinosaur species before finally mustering the will to pull on my pants and go hunting for coffee. During the daylight hours, walking through dark woods, frosted fields, and eventually, bustling city streets, I would still find myself compulsively reaching for the phone. The urge could be struck by something completely innocuous. For instance, when my feet became sore, I would sometimes search for symptoms of tendonitis or gout. This did not help my general morale.

But just as often, the phone would prove itself useful. On multiple occasions, my travel plans were thwarted by busy roads that were just as impassable as the stretch of highway I encountered on Day One. With enough cellular service, I could search for alternative pedestrian-friendly passage, which took the form of bike paths, hiking trails, and in one unfortunate instance, a culvert brimming with highway runoff and garbage. That same night, I arrived in the town of Leicester, at the duplex I had booked via Couchsurfing, only to find that the hosts missing and unreachable by phone! Rather than suffer in the cold, I was able to book an emergency motel room with my phone, where I retired to and spent several glorious hours eating chicken fingers.

Two weeks later, as I stood on the sands of World’s End, looking out at the steely waters of the Atlantic, I had given up on adopting anything resembling a purist approach to expeditioning with an iPhone. As much as I enjoyed those long spans of disconnection from the digital world, I would have been a lot more miserable - possibly a lot more dead - without my iPhone. Maybe that’s a sad commentary on what it means to be a denizen of the Internet Age. Perhaps when I’m older, jaded by further decades of scrolling and information binging, I’ll find it easier to tune out and smell the manure: to be okay with being alone. Or not. By the year 2045, our electronic devices could be permanently integrated into the human body, like a pair of earrings: inescapable and always ready to distract. Can you imagine? I certainly have.

But that is neither here nor there.