Greylock War Memorial, Appalachian Trail

Starting from Bear Mountain Bridge, the path climbed steadily, leading me along the western shore of Canopus Lake, where its glassy surface reflected the sky. A bit further, Nuclear Lake appeared—an unexpectedly peaceful spot despite its ominous name, a lingering reminder of the nuclear research facility that once sat on the lake's shore.

I passed the iconic Dover Oak, a 300-year-old tree with a massive trunk circumference of 20ft (6mn). This giant is the largest tree on the AT and is proudly listed on New York's "Big Tree" Registry as the largest White Oak. Not long after, I reached the Appalachian Trail Station, a small, unique railway stop set up especially for hikers who may want to hitch a train ride to or from New York City. It's so tempting to take a side trip!

I resisted the urge to stop and pressed on. As soon as I waded across Dover Hollow Brook, I crossed into Connecticut, the tenth state on my journey—only four more to go. I crossed a graceful arched bridge over Tenmile River near its confluence with the Housatonic. Further along, I came upon the historic Bull's Covered Bridge, a 19th-century structure and one of just three surviving covered bridges in the state. Named after Jason and Isaac Bull, who built the original bridge a century earlier, it remains a significant landmark in Connecticut's history.

The climb up Schaghticoke Mountain came next, one of the most demanding sections of the trail, with steep, rocky stretches that really tested my stamina. I pushed on to St. John's Ledges and Caleb's Peak, where rocky outcrops offered gorgeous views of the Housatonic Valley. Thankfully, the trail levelled along the Housatonic River Walk, a serene 5mi (8 km) stretch, giving my legs a much-needed break. I spotted herons wading in the shallows and chipmunks darting through the underbrush, adding some fun moments to my hike.

Near the Massachusetts border, I faced the tough ascent of another Bear Mountain, the highest peak in Connecticut. The climb was steep, with rocky outcrops and thick foliage, making it a challenging hike. But as I neared the summit, the trees began to thin, and I was rewarded with clearings offering sweeping views of the surrounding landscape. I paused here for a bit to rest, hydrate and soak in the views. After a much-needed break, I was excited to descend and walk straight into Massachusetts, the eleventh state.

Mount Everett followed, with another demanding ascent, and then onto a series of lakes and rocky ridges where the Taconic Range and its rugged terrain gave way to the rolling hills of the Berkshires. Nestled within the Berkshires is Great Barrington, a lovely town where I resupplied and rested before steeling myself for the final challenge of this section—the climb up Mount Greylock, the highest peak in Massachusetts.

Mount Greylock was a relentless climb to 3,491ft (1,064m). Near the summit stands the Veterans War Memorial Tower, which resembles a lighthouse. Originally built in 1932, the tower was eventually demolished due to harsh weather conditions that made it difficult to maintain. However, the local community rallied to rebuild it, and a new tower was completed in the mid-1970s. 

Mount Greylock also holds literary significance. Herman Melville, the famous author of Moby-Dick, dedicated his 1852 novel Pierre, or The Ambiguities, to the mountain. Melville lived nearby and was inspired by the beauty and solitude of the area. Much of the novel was written while living here, and he saw Mount Greylock as a symbol of deep personal and philosophical meaning, themes he explored in the book.