Connecticut’s highest points have, in a sense, been borrowed from its neighbors. Geologically, they’re part of the Taconics and the Berkshires—so, New York and Massachusetts, which have high points to spare. In fact, Mount Frissell—at 2,380 feet, the closest Connecticut comes to the heavens—spans the border with Massachusetts, which a Connecticut summiter would then have to cross to get to the 2,454-foot peak.
I chose to hike Bear Mountain instead, which had boasted Connecticut’s official highest point until the 1940s, when the United States Geological Survey took more sophisticated measurements. Bear is still described as holding the highest point on a stone plaque at its summit, and it still lays claim to being Connecticut’s tallest complete mountain for lying wholly within the border.
I was also drawn by the name, which, unlike many mountains, is not that of some 19th-century dignitary but of a native inhabitant. Generally fearful of encountering bears on wilderness hikes, I thought it would be too rich if this were to actually happen on Bear Mountain. When I had gotten fairly close to the summit, a hiker wearing a helmet with a GoPro camera offered assurances. “They’ll leave you alone. Trust me. The only place [experts] really emphasize bringing a can [of bear repellent] is the Smoky Mountains in Tennessee. Otherwise, I think they’re more afraid of us than we of them.”
This hiker had taken an Uber from Boston, where he teaches, to the Connecticut-New York border, where his hike commenced. At the end of Day 5, in the parking lot of a grocery store in Salisbury, he had encountered a self-designated bear tracker, a woman who’d just spotted a bear raiding her backyard bird feeder for the hundredth time, and so now she was in diligent motorized pursuit. “And she gave me the story of that, and then she just points behind me”—and there it was. The hiker pantomimed turning around in amazement. “Looked like a 300-pounder.” The next day, the hiker found himself in the odd position of entering the woods to effectively get away from a bear.
Having approached the summit from the opposite direction, I encountered mostly chickadees, whose alarm chirps resemble the name we’ve given them, and seemed to suggest that I was the bear. It was a dry, cloudless day with a soft and steady breeze. I had reached Bear’s foot from an unpaved access road to the west. (You can also get there, at a more leisurely pace, from State Road 41 to the east.) I crossed narrow brooks on sturdy plank bridges and passed a small rustic cabin, available by reservation to overnight hikers, at a wooded overlook. This shady approach was broken by occasional sunlit clearings, which were carpeted by lacy ferns. In those spots, the path narrowed to human width.
Arriving at a T-junction, I could turn right to go up to the summit, or left to go downhill. A sign announced that this was the Appalachian Trail, which meant that I could turn right to go to Georgia or left to go to Maine. The possibility of this was reinforced when I took a left and, not 20 paces out, crossed the border into Massachusetts. A small, easier-to-miss sign marks the crossing.
The path descended until it reached a substantial stream and a clearing designated for tents. It then followed the stream closely. After about 15 minutes, hemlock-strewn inclines closed in on both sides to give the scene a primordial intimacy. This area, Sages Ravine, was also characterized by dramatically carved boulders and banks that corralled the water into cascades, elbow turns and pools. At some points, the trail and the boulders were essentially the same, the rock forming a kind of rough stairway to postcard views of the action, before eventually crossing the stream toward the Berkshires.
Resisting the temptation to carry on, I turned around to retrace my steps to the T-junction, then proceeded up the side of Bear Mountain. The going was steep, a scramble over rock ledges that takes you up 500 feet in less than half a mile. The summit, made several feet higher by the remains of a stacked rock tower, afforded a view of other wooded hills to the northeast. Further down the path could be seen a more panoramic expanse of sky and greenery to the southeast. I half-expected the highest point to show me the extent of the state it’s in, all the way back to New Haven and the Sound, but the part of Connecticut I did see was gratifyingly undeveloped: state-protected woods and undotted fields extending to Salisbury’s quaint center.
This too is part of the Appalachian Trail, and that’s no coincidence. The “A.T.” was conceived in the 1920s, in part, as a showcase for high points. It would have started at the highest peak in the south—Mount Mitchell in North Carolina—and ended at the highest peak in the northeast—Mount Washington in New Hampshire. Over the years, as the trail was built, it was expanded and reconfigured to include highest points in Tennessee, Virginia, Massachusetts and Maine. The Connecticut section of the trail, including the Bear Mountain traverse, was the first to be completed, in 1933. Bear is both the lowest of the highest points visited by the trail and, by far, the closest to a state line. It’s the culmination of a state leg that generally lasts about 6 days.
Late summer is when northbound thru-hikers—those who attempt to hike the Appalachian’s entire 2,190-mile span—tend to arrive at this leg. I had encountered six or seven hikers while I was there, but I could easily pick out the one who’d been at it for over half a year. He was heavy but steadfast in his tread, and his gear was visibly sodden and faded compared to mine. I assured him the summit was close and asked him about his trip.
He had started his hike in Georgia on February 1st “in snow and ice” shortly after his 66th birthday, and he couldn’t say he minded, exactly, being drawn up and down mountains the whole way. “It would be nicer if there was a ridge that went up gradually,” he shrugged. “But it is what it is.” He had fond recollection of the Shenandoahs and hated Pennsylvania, which is notoriously rocky. “Connecticut,” he averred, “has its share of hills and a little bit of exposure and rock. But it’s still very pretty.” As I think is the case for most thru-hikers, the state’s highest point was less significant to him than the border crossing, along with its selection of spots to bed down, which he knew awaited him a little farther on.
The top of Bear Mountain was a tranquil place to stop, even in the considerable stretch of it without a view. Naturally exposed to wind and weather, it offered striated ridges of exposed bedrock to sit on, abundantly ringed by pitch pine and scrub oak. From the actual summit, I kept walking south, and here the descent was gradual, marked as such by a heightening of surrounding trees. Leaving the Appalachian Trail to return to my car, I took a soft path through low ground, sporadically puddled and continuously hemmed by a vivid green sea of low-growing mountain laurel. The call of a wood-pewee—which sounds like the whistle people use to say “over here”—greeted me when I emerged.
Connecticut’s highest peak was squarely a day trip, sure to get me home well before dark. But that night, I would be thinking of bears and thru-hikers, both sleeping on the mountainside after a hearty meal in town.
Written and photographed by David Zukowski.
