Men's Journal

Finding unexpected solitude — and great pubs — along the new 220-mile New England trail.

Text and photographs by Christopher Percy Collier 

Heading into the woods at the end of a cul-de-sac of gated mansions on a foggy June morning, I thought, It’s Connecticut — how tough could it be? To ramp up the adventure in this tame southern corner of New England, I’d bragged we could turn today’s 13-mile jaunt into a full-bore trail run. But that was before a thigh-busting elevation gain put us on top of a wild ridge with expansive views of the Farmington River, a trout-filled flow punctuated by saltbox houses, Victorian churches, and taverns dating to the 1800s. It was before we hopped from boulder to precarious boulder along a cliff that doubles as a launch site for hang gliders, followed by a dizzying stair climb up the six-story Heublein Tower. And it was before my hiking partner Tim almost stepped on a copperhead coiled on the trail. “Um,” he said, reaching for a stick to usher the snake into the underbrush, “maybe we should slow the pace a bit?” 

It’s been more than 25 years since the Feds stamped “National Scenic” on a hiking trail, but on March 30, President Obama added three more, including the New England National Scenic Trail, to the list. 

“The idea is to make a long-distance footpath that can be experienced over a few days or longer,” says Jamie Fosburgh of the National Park Service. “You won’t be able to thru-hike the trail from one end to the other immediately.”

Well, you can come close.

SECTION 1: Middletown to Rattlesnake Mountain

The NENST begins along the high banks of the Connecticut River in Middletown. From there it climbs the steplike rocks of Mica Ledges, Broomstick Ledges, and Bluff Head, with views of Long Island Sound. “It’s one of the most scenic sections of the trail,” says Eric Hammerling, executive director of the Connecticut Forest and Park Association. 

A few miles north, hikers can admire views from Castle Craig, a rock tower built in 1900 to resemble a European fortress. Further on, scrambling up a house-size rock on the slope of Ragged Mountain, I get an intimate introduction to traprock, the main geological feature of the trail. At the top, a long plateau with 80-foot drops, I meet local EMS climbing guide Matt Shove.

Trap is Swedish for step, he says, and it’s rippled with vertical edges. “In Yosemite, you can only climb the cracks because the faces are so smooth. Here you can climb the cracks and the faces.” Climbing legend Fritz Wiessner put up routes in the 1930s with hemp rope. 

I boulder an easy section while Shove hikes to the bottom of the face to climb a 5.8 route called Broadway. Fifteen minutes later he’s on top, explaining how Ragged Mountain was saved from develop-
ment in the 1990s by climbers who banded together to help buy it; now, 55 acres are protected. Dangling from the rock, he points to Rattlesnake Mountain, 15 miles north, another great climb on the trail.

SECTION 2: Hill-Stead to Westfield River

The New England trail is unlike any other National Scenic Trail in that it runs through suburbia. While the 2,175-mile Appalachian Trail abuts 20 federally protected wilderness areas, the NENST doesn’t cross any as it meanders through the middle of the Boston–New York megalopolis. More than 2 million people live within 10 miles of this path. 

Cultural amenities like the Hill-Stead, an art museum that backs up to the trail, come with the territory (Farmington, Avon, Simsbury), letting you end a day’s hike with a cold beer, a hot meal, and a soft bed. Less than a mile away, the landmark Farmington Inn offers luxurious rooms for $149. Eight miles up the trail, we stop at the Avon Old Farms Inn, a tavern converted from an 1800s blacksmith shop. Under wooden beams adorned with bayonets and saddles, we reward our muddy romp with clam chowder, burgers topped with boursin cheese and crimini mushrooms, and pints of red Thomas Hooker Ale. 

From Simsbury, the trail drops into Tariffville Gorge, where trout and kayakers both shoot through Class II–III whitewater. From there it heads north into Massachusetts. 

SECTION 3: Westfield River to Belchertown

The trail traverses a swamp on a series of footbridges and then crosses the gushing Westfield River, which for 56 years has hosted an April whitewater canoe race. About 20 miles north, on the outskirts of the 2,082-acre Mount Tom State Reservation, the path climbs steeply to a protruding ledge. 

We thought this climb would take hours, but some kids at a coffee shop near the base point to a shortcut. The steep trail is littered with tons of long, rectangular boulders, but within 45 minutes we’re on the top with 180-degree views of the wooded valley below. 

Farther north, a seven-mile stretch of unbroken woodland in Holyoke Range State Park offers four quick peaks — Hitchcock (1,005 feet), Bare (1,010 feet), Norwottuck (1,106 feet), and Long (920 feet) — as well as several “horse caves” used by farmers to hide from the Feds during Shays’s Rebellion in 1786. 

Hiking up Norwottuck, we pass two of the mere handful of people we see on the entire trail. On top, we soaked in a vista without a single man-made structure, as if a giant spread a green blanket over a cluster of massive pillows. The farther north you go on the NENST, the wilder it gets.

SECTION 4: Amherst to New Hampshire

There are no museums or mansions as the trail passes Farley, 20 miles from New Hampshire. In Wendell State Forest, home to one of four shelters along the NENST, we don’t see anyone at all. On a clear Saturday night in June — the height of camping season — we have the 7,566-acre park to ourselves (excepting the yapping waterfowl in the pond by our campsite). The only visitors allowed to camp are hikers traveling this virtually unknown trail.

As we boil water for our freeze-dried dinners, I realize I’ve underestimated the New England trail. We’re in the most crowded quadrant of the country, but being on the trail sets us apart. Even in the unlikely hinterlands of southern New England, it seems membership has its privileges.

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