I Spent a Year Hiking 160 Miles Through Massachusetts. Here’s What I Learned

Photos by Madeline Bilis. Reproduced by permission of The Countryman Press. All rights reserved

Eastern Massachusetts is the loveliest place on earth. I can say this with 100 percent certainty, because I spent the better part of last year exploring all its nooks and crannies, trails and coastlines, hills and meadows. Every weekend for months, I went on a hike—oftentimes several—in this part of the state. Then I got home and wrote furiously, cataloging every one of those hikes for a new guidebook I was writing: 50 Hikes in Eastern Massachusetts. 

From the rocky ledges of the Blue Hills Reservation to the sandy stretches of the Cape Cod National Seashore, I conquered the region’s best-known trails and hidden gem walks alike. With notebook in hand, I found myself hiking in pouring rain, in cold, and in extreme heat, but also on perfect fall days as sunlight filtered through rust-colored leaves, with friends both new and old beside me. Fifty hikes seemed a bit daunting at first, but after completing each one, it became easier and easier to jot down all the details I wish I’d known when I started. More than 160 miles and 240 pages later, I had a hiking guide to match my newfound appreciation for all the things I’d been overlooking in my own backyard.

The author at Willard Brook State Forest / Photo by Adam Banks

The assignment took me places I might never have visited otherwise, and revealed gaps in my Bay State credentials. I grew up here, went to college here, even worked as an associate editor at Boston magazine—but I never had a reason to stroll through downtown Medfield or watch the sun set over Fairhaven. One day, after a morning spent hiking the magnolia-scented paths of Gloucester’s Ravenswood Park, all I wanted for lunch was a chicken salad sandwich and an iced tea. If I’d been visiting the North Shore for any other reason, I probably would have spent the afternoon at a new beer garden, or in a hip little cafe in Rockport. But this time, my sweaty hiking partner and I ducked into a pub near the harbor, where I listened to two regulars at the bar dissect the menu at Wahlburgers. (Overrated, they said.)

Near Great Brook Farm State Park in Carlisle I stumbled across a “pug social,” where pug owners converged upon some fairgrounds to celebrate their pudgy little dogs with a costume contest and so, so many pug-themed accessories. I learned about a grisly 1900 murder at Breakheart Reservation and I pulled over to frolic through a roadside sunflower field in Littleton. I poked into centuries-old house museums (the best kind of museum, in my opinion) and sampled slices from perhaps one too many Insert-Town-Name-Here Houses of Pizza. 

Twenty-seven people accompanied me on my 50 hikes, though hardly in equal proportion (shout out to my best friend in the world, Adam, who joined me on a whopping 38 hikes and drove me to every trailhead). They were current and former coworkers, childhood friends, and family members, ranging in age from just a few months to 57 years old. The leafy peace of the trail provided endless opportunities for conversations about life, death, and everything in between—I heard from new parents about the joys of raising kids, I debated long and hard about the future, I reminisced about Emerson with my college roommate, and sometimes I just complained loudly about all the bugs.

Boston magazine contributing editor Chris Sweeney and his daughter, Stella, at Ipswich River Wildlife Sanctuary / Photo by Madeline Bilis

Not long after I had started hiking for the book, I invited my brand-new colleague, Boston magazine’s wellness editor Tessa Yannone, to go to Middlesex Fells with me. A 7.5-mile trek can test the stores of conversation for even the oldest friends, let alone someone I barely knew. But one of the best lessons I learned while working on this project was that spending hours with another person in the woods, free from the distraction of phones, Twitter, and the general horrors of this world, leaves a lot of room for forging a real connection with someone. There was time for meaningful conversation! Self-reflection! Goofiness, fun, and teary-eyed laughing fits! Today, Tessa and I are good pals, and I have a hike through the Fells to thank for it. 

Hikers Jackie Cain, Adam Banks, and Rachel Kashdan at the Blue Hills Reservation / Photo by Madeline Bilis

Full of long talks and small-town wonders, my year spent writing this book put the best of Massachusetts on display for my fellow hikers and me. This fall, I encourage you to get out there and discover all the region has to offer—and maybe use my book as a guide. You don’t have to pore over it cover to cover like I know my Grammy will, but I hope it helps you appreciate that the area’s beauty lies in its endless possibilities for exploration, both on and off the trail.

50 Hikes in Eastern Massachusetts will be released on August 20, 2019. A launch event for the book will take place at Brookline Booksmith on August 22 at 7 p.m. Tag your hiking photos with @50hikeseasternmass.