Mount Greylock stands as the highest point in Massachusetts, its summit a commanding vantage spilling views across four states on clear days. The hike here offers more than elevation; it’s an engagement with a landscape fiercely itself, where dense forests lean close and wind whips over rocky ledges daring you forward.

Starting at the base, expect roughly 7 miles round trip with an elevation gain near 2,000 feet—enough to test stamina without demanding technical climbing skills. Trails like the Appalachian and others wind through mixed hardwood forests where spring’s newborn leaves reach toward the sky and fall’s amber light filters through branches. Underfoot, roots grip earth and loose stones whisper of careful footing. The terrain varies—well-maintained paths mix with steeper stretches that reward effort with expanding views.

Hydration is non-negotiable. Water sources near trailheads provide a start, but bring at least two liters and a filtration method if you plan a longer trek. Footwear should be sturdy with good grip; the terrain can turn slick with dew or rain. Timing your ascent matters—early mornings typically offer cooler air and fewer crowds, while late afternoons can be brisk with the wind’s sudden charge.

At the summit, the iconic War Memorial Tower stands like a beacon. From here, vistas unfold—Vermont’s Green Mountains to the north, the Taconic Range westward, Connecticut’s hills to the south, and the distant Berkshires beneath. The sky often breathes with shifting layers of cloud and sunlight, creating a dynamic backdrop to the landscape’s calm spread.

Practical preparation meets wild reward. This hike requires respect: the mountain isn’t conquered; it’s encountered, each step an exchange with nature’s relentless character. With clear planning and measured vigor, summiting Mount Greylock becomes an adventure both accessible and richly satisfying.