Mount Greylock rises with a deliberate presence in the Berkshire landscape — the highest summit in Massachusetts at 3,491 feet. Hiking to its peak is a journey through shifting forests where the trees seem to lean closer as you ascend, and the fresh mountain air pulls you forward, steady and unyielding. Starting from Cheshire, Massachusetts, the approach offers a clear path unfolding through mixed hardwood and evergreens that engage your senses and challenge your stamina.

The most popular route, the Thunderbolt Trail, stretches roughly 7 miles round trip with an elevation gain just north of 2,000 feet. This trail weaves through dense woods, rocky sections, and moss-covered roots that demand sure footing but reward with dynamic terrain that never grows dull. Each step upward feels like a conversation with the mountain itself — nature’s elements daring your resolve as you push against the incline.

Reaching the summit reveals why this climb holds a revered place among hikers: sweeping 270-degree panoramic views that extend across the Taconic Range, the Green Mountains of Vermont, and on clear days, the distant Adirondacks. The observation tower crowns the peak—an ideal vantage point to absorb the horizon’s vastness without obstruction.

For timing, early mornings or late afternoons offer softer light and cooler temperatures, enhancing both comfort and the visual drama of the scenery. Seasons color the experience differently — spring brings wildflowers peeking through thawing soil; summer blankets the forest in vibrant greens; fall sets the treetops aflame with red, gold, and orange hues, while winter cloaks the ground in snow, turning the ascent into a quiet, crystalline challenge.

Practical preparation is crucial. Solid hiking boots with ankle support will negotiate the uneven, root-strewn paths, while layers help adjust for weather changes as altitude shifts. Carrying at least two liters of water keeps you hydrated through the steady climb. A packed snack will also fuel those moments when the summit’s promise feels just within reach.

Respect the mountain’s strength—its weather can shift without warning and the trail demands focus. Yet, the summit rewards handsomely for every step taken: a moment standing fiercely alive at Massachusetts’ highest point, surrounded by nature’s unbroken expanse. This hike balances challenge with spectacle, making it a practical yet thrilling goal for anyone seeking to engage directly with the wild heart of the region.