The summit of Mt. Greylock is the highest peak in Massachusetts. During the off season, it is accessible, however it is a strenuous day hike at almost 10 miles roundtrip. With winter offering quickly changing weather conditions, you may decide to stick to some of the side trails of Greylock and save the summit for late Spring. The Hopper Trail is a great option, as it stays along frozen creeks and makes the scenery more interesting.
The trailhead begins at Haley Farm in Williamstown. Heading south from Rte 43, take a left on Hopper Rd and follow to where the road ends; there is a parking area on the right. You'll walk past the farm and follow the signs to the trail. There are many other trails that branch off of the Hopper, depending on your endurance or interests. Massachusetts' Department of Conservation and Recreation provides these options, including maps that are very helpful for planning your journey. The hike I am suggesting is under option 3 of Year-Round Day Hikes.
The Hopper is a bowl-shaped valley that's been recognized as a National Natural Landmark since 1978. The area's old growth forest has a variety of trees that are over 150 years old, including red spruce conifers. In the winter, there is not much wildlife to be seen. The trees are bare and it's as if the whole forest is asleep. I find these winter hikes to be very serene and the frozen chunks of ice are captivating.
Once you get up to Stony Ledge, you'll find several options. You can continue further up on either the March Cataract Trail or Deer Hill Trail for waterfall viewings. Either option will return back to Stony Ledge via Sperry Road. From there, you'll continue on the Haley Farm Trail to the trailhead parking. Whatever you decide to do, the hike up to Stony Ledge and back around to Haley Farm makes for a nice winter hike at roughly 3 miles in total. The side trips to the waterfalls will add a couple additional miles.
Spring is less than a month away and before we know it, the trees will start blooming and our landscape will return to its various shades of green. The days are already getting a bit longer and I encourage you to step outside a little earlier than you may normally. Take advantage of a beautiful winter morning and head out to explore the side trails of Mount Greylock.