Hiking Mount Greylock in the Winter

By Sabrina Damms
January 08, 2026


ADAMS, Mass.— Mount Greylock is a place of mystique, rich in history and natural beauty. Its breathtaking vistas have inspired world-renowned authors and artists for generations.

Mount Greylock is the highest point in Massachusetts, being 3,489 feet, covering 12,000 acres, has over 70 miles of trails and is a stop along the Appalachian Trail.

Atop the mountain, the Massachusetts Veterans War Memorial can be seen from several angles in surrounding towns and cities. This 93-foot tower honors the veterans who fought in World War 1.

Even in the winter, when the road to the summit is closed, visitors admire the monument rising above the snow-covered hills. 

One would assume that the destination would be undisturbed in the dead of winter. However, Mount Greylock Visitors Center keeps activity thriving with educational programming including a photography club hike for all abilities, discover greylock guided hikes, tree identification hikes, winter wildlife tracking, and so much more. Events can be found here

Adventurous hikers willing to brave the mountain’s trails to the summit in winter are rewarded with tranquil silence and traces of wildlife that endure through the season. Although a beautiful sight, the remote location and challenging conditions can delay emergency assistance, so caution is essential.

According to previous hikers, the trudge to the summit in the winter typically takes anywhere between four to eight hours, or more, depending on the chosen route, snow and ice conditions, and the visitor's fitness level. 

A successful ascent requires careful planning and essential winter hiking gear: food, water, a first aid kit, a map, sturdy footwear, traction devices like microspikes, waterproof and warm clothing, hiking poles, and a whistle or signal mirror.

Winter hiking safety tips here.  

Suggested trails for year-round hiking include:

  • Rounds Rock Trek– Distance: 6.9 miles (11 km), Time: 5-6 hours, Elevation gain: 920 ft. (280 meters), Ability: moderate
  • Bradley Farm Trail Distance–1.8 miles (2.9 km), Time: 90 minutes, Elevation gain: 424 ft. (129 meters), Ability: easy
  • Views and Falls– Distance– 5.5 miles (8.8 km) plus options, Time: 4-5 hours, Elevation gain: 1,460 ft. (445 meters), Ability: strenuous
  • Greylock in the Round Distance– 13 miles (20.9 km) plus option, Time: 9 hours, Elevation gain: 2,390 ft. (728 meters), Ability: aggressive
  • Roaring Brook & Stony Ledge Distance– 5.6 miles (9 km), Time: 4-5 hours, Elevation gain: 1,460 ft. (445 meters), Ability: strenuous
  • Thoreau’s Footsteps Distance– 9.6 miles (15.5 km), Time: 6 hours, Elevation gain: 2,191 ft. (668 meters), Ability: aggressive
  • Bellows Pipe & Ragged Mt. Trailhead– Distance: 5 miles (8 km), Time: 4 hours, Elevation gain: 1,288 ft. (393 meters), Ability: moderate to strenuous 
  • Cheshire Harbor Trail Trailhead– Distance: 6.6 miles (10.6 km), Time: 4-5 hours, Elevation gain: 2,100 ft. (640 meters), Ability: moderate to strenuous

Details, location, and map of each trail here

Depending on the chosen trail, you may have successfully made it to the summit where you will be rewarded with a well earned magnificent view. On a clear day you can look out 90 miles from the top of the summit. 

The mountain has been the inspiration to many legendary writers including Herman Melvile, Henry David Thoreau, Nathaniel Hawthorne, and J.K. Rolling because of its beauty and supernatural folklore.

It was the inspiration behind Melvile’s Moby Dick and is believed that the whale was inspired by the way Mt. Greylock looked from the window of his Arrowhead home on a snowy winter day in Pittsfield Massachusetts.

Thoreau was inspired by Mt. Greylock after spending the night atop the mountain in 1884 and awakened to fog which he referenced in his first novel calling it "an undulating country of clouds."

Nathaniel Hawthorne references the legendary summit in his short story “Ethan Brand”, which he wrote after hiking the mountain in the dark. His story takes a sinister tone telling the story of a man who operates a furnace on Mount “Gray Lock” and is obsessed with finding the “Unpardonable sin.”

More recently, J.K. Rolling referenced the summit in one of her online short stories about North American witches and wizards that attend a school on top of Mount Greylock called Ilvermorny.