Mount Greylock, standing tall at 3,491 feet, challenges hikers to reach the highest point in Massachusetts. The journey begins in Williamstown, where forest trails draw you into an evolving landscape—trees lean in as if to watch your ascent, while breezes playfully dare you forward. The climb is a steady confrontation with nature’s rhythm: rocky roots gripping the earth underfoot, the scent of pine mingling with damp soil, and the unveiling of panoramic views that reward persistence.

The most popular route from the base parking area is the Hopper Trail to the Appalachian Trail, stretching approximately 4.5 miles one way, with an elevation gain of about 2,000 feet. The terrain alternates between shaded woods and open ledges, where the wind speaks in gusts, nudging you toward the summit’s fire tower. This vantage point grants sweeping vistas across the Berkshires, the Taconic Range, and, on clear days, even the Catskills.

Approaching the summit, the forest thins and the landscape exposes its raw bones—granite outcrops that firmly remind you nature is fiercely itself here. The fire tower provides shelter and a rare elevated perspective, perfect for pausing, refueling, and catching your breath.

Preparation is key. Footwear with solid grip will manage the rocky and sometimes slippery paths, while adequate hydration ensures you meet the mountain’s demands without faltering. Starting early avoids afternoon crowds and their trail spills, and catching the summit near sunrise or late afternoon enhances the clarity of those wide-open views.

Though popular, Mount Greylock respects those who tread lightly, offering a terrain that’s challenging yet accessible for most moderate hikers with a good base level of fitness. The mountain’s moods shift rapidly, especially in shoulder seasons, reminding you that nature on a mountain owns its own pace and conditions.

Whether you’re a seasoned hiker or a weekend adventurer, the trek up Mount Greylock provides an honest, invigorating experience. It’s more than a hike; it’s an invitation to meet a peak that holds stories in its stones and legends in its sweeping skies.