Prior to the arrival of Europeans the Mahican people were closely associated with this region.
The traditional trade route connecting the tribes of the Hudson and Connecticut River valleys (today, Route 2, known as the Mohawk Trail) passes beneath the northern flank of Mount Greylock.

The mountain was known to 18th century English settlers as Grand Hoosuc(k).
In the early 19th century it was called Saddleback Mountain because of its appearance (Saddle Ball, the name of the peak to the south, still reflects this).

The origin of the present name of Greylock and its association with the mountain is unclear.
It first appeared in print about 1819, and came into popular use by the 1830s.
It is believed to be in tribute to a legendary Native American chief, Gray Lock.
Gray Lock (c. 1670-1750) was a Western Abenaki Missisquoi chief of Woronoco-Pocomtuc ancestry, born near Westfield, Massachusetts.
Gray Lock distinguished himself by conducting guerrilla raids into Vermont and western Massachusetts.

Timothy Dwight IV, President of Yale University, along with Williams College President Ebenezer Fitch, climbed Greylock in 1799, probably over a rough route cut by a local pioneer farmer Jeremiah Wilbur (in that time more land had been cleared on the slopes for farming than today).
His account in Travels in New England and New York describes the experience, although he noted the summit vegetation was so thick he and Fitch had to climb a balsam fir tree to get a better view:
(Saddle Back) is the highest land in the state ... Its southeastern front is extensively visible throughout Berkshire, and from high elevations in the states of New Hampshire, New York, Vermont, and Connecticut at very great distances ... During a great part of the year, it is either embosomed or capped by clouds, and indicates to the surrounding inhabitants the changes of weather with not a little exactness.
Prior to the arrival of Europeans the Mahican people were closely associated with this region. The traditional trade route connecting the tribes of the Hudson and Connecticut River valleys (today, Route 2, known as the Mohawk Trail) passes beneath the northern flank of Mount Greylock.
The mountain was known to 18th century English settlers as Grand Hoosuc(k). In the early 19th century it was called Saddleback Mountain because of its appearance (Saddle Ball, the name of the peak to the south, still reflects this).
The origin of the present name of Greylock and its association with the mountain is unclear. It first appeared in print about 1819, and came into popular use by the 1830s. It is believed to be in tribute to a legendary Native American chief, Gray Lock. Gray Lock (c. 1670-1750) was a Western Abenaki Missisquoi chief of Woronoco-Pocomtuc ancestry, born near Westfield, Massachusetts. Gray Lock distinguished himself by conducting guerrilla raids into Vermont and western Massachusetts.
Timothy Dwight IV, President of Yale University, along with Williams College President Ebenezer Fitch, climbed Greylock in 1799, probably over a rough route cut by a local pioneer farmer Jeremiah Wilbur (in that time more land had been cleared on the slopes for farming than today). His account in Travels in New England and New York describes the experience, although he noted the summit vegetation was so thick he and Fitch had to climb a balsam fir tree to get a better view:
(Saddle Back) is the highest land in the state ... Its southeastern front is extensively visible throughout Berkshire, and from high elevations in the states of New Hampshire, New York, Vermont, and Connecticut at very great distances ... During a great part of the year, it is either embosomed or capped by clouds, and indicates to the surrounding inhabitants the changes of weather with not a little exactness.
Mount Greylock