Mount Greylock is located in the Berkshire Mountains, and is the highest mountain in Massachusetts. At 3,491 feet, Greylock wouldn't seem to be too remarkable, but this is actually one of the most scenic mountains in the Eastern United States. It is so inspirational that legend has it, Mount Greylock's long, saddle-like shape inspired Herman Melville to write "Moby Dick". He was known to have great fondness for the mountain, even setting up a special observation deck at his home (near Pittsfield) so he could view Greylock whenever he desired.
When you travel to Greylock, it is obvious why people believe the legend and why Melville went out of his way to keep the mountain in his sites. Greylock can be seen for miles around, and is a quite impressive site given that is rises nearly 2,700 feet above the surrounding town of Adams, Massachusetts. Furthermore, it's very colorful, and has a steep slope that shoots up into the sky, unlike most mountains you'll find of this height in New England. This is because Greylock is a Monadnock - a lone, isolated mountain rising steeply above the surrounding area.
You can either drive to the summit, or take moderate-to-long day hikes (the shortest taking less than 90 minutes to reach the top). The summit offers great views of the Green Mountains to the north, Catskills to the southwest ,and the Adirondacks to the northwest. On a clear day, you can even see the White Mountains of New Hampshire. However, the summit area itself is very large, and once on top, you need go to different look-out points to see the Eastern, Western, Southern, and Northern views.
As for the summit tower, I do not recommend wasting your time to climb it. The windows are grimy, making the view very poor, and the view points at the sides of the mountain are much clearer and more interesting. There is so much to take in at the summit it is better (and more enjoyable) to take the time to walk around it to see all the splendorous views.
Mount Greylock is located in Berkshire County in the Northwest corner of Massachusetts. It is rather isolated from major cities. The nearest "city" is Albany, New York. Getting to Greylock from most major urban areas requires getting to Lanesboro, Massachusetts (which is to the south of Greylock). Coming from the North, you will want to reach the town of North Adams.
From New York: To get to Lanesboro from the New York State Thruway (I-87), get off at I-90, and follow it to 90 West towards Albany until you hit Route 20 East. Take that into Massachusetts until you hit Route 7.
To get to Lanesboro from the Taconic Parkway in New York, take it to I-90, and follow I-90 East to exit#2 in Lee. Follow Rt. 20 to Rt. 7, pass Pittsfield, and go another 6 miles.
From Massachusetts: If you want to take the MASS PIKE, take it to exit 2 in Lee. Follow Rt. 20 to Rt. 7, pass Pittsfield, and go another 6 miles to Lanesboro.
To take a scenic (and more direct route) from Boston, take Route 2 across the state. It is about 130 miles to North Adams, but is more scenic than the MASS PIKE. From North Adams, you can travel South on Route 7 or Route 8 for whichever trail you want to hike.
When driving to the summit, watch for the Mount Greylock Reservation and Visitor signs on the right of Route 7, two miles north of Lanesboro. Turn right at North Main St., the visitor center is on the right just before entering the gates to the reservation where you can obtain maps and trail information. Continue on Rockwell Rd. for 9 miles to the summit.
There are no permits or fees required to hike Mount Greylock.
The Rockwell and Notch Roads to the summit and the Lodge are closed form Columbus Day to Memorial Day.
There are no parking passes required, but you will be charged $2.00 to park at the summit parking lot. Overnight parking is only allowed on Hopper Rd., Sperry Campgroad, the Visitor Center, and Bascom Lodge. Great care should be taken while hiking in the sub-Alpine forests of Greylock, Fitch, and Saddleball Mountains. These are the only boreal forests in the state, so protect the trail that pass through these unique forests.
Mount Greylock is generally a day hike. However, there is camping along the Appalachian Trail which travels 90 miles through Massachusetts. There are also multiple campsites at the Mount Greylock State Reservation. There may be fees for some campsites, and the most popular spots may require making reservations.
Camping is only allowed in Sperry campground and designated campsites. There is no camping within the Hopper Natural Area except for Wilber's Clearing Shelter.