Best Hiking in the Berkshires Hills and Mountains and Walks in Berkshires State Forests and Parks.

Hiking in the Berkshires takes you through hills and woods and lets you follow in the footsteps of such New England literary giants as Melville, Hawthorne and Thoreau. The Appalachian Trail (AT) runs through 90-miles of the region culminating with the challenging hike to the summit of Mount Greylock – Massachusetts highest point at 3,487-feet. Other long distance trails in the region include the South Taconic Trail (STT) and the Taconic Crest Trail (TCT).

Here are some of the scenes you’ll discover…

Hiking in the Berkshires offers challenging trails on Mount Greylock in the north, and easy hikes up Monument Mountain in the south, and plenty of walks through forest paths and mountain streams in the destinations between.

But there are plenty of casual walks in the forests that focus more on the beauty and diversity in the woods than sweeping views of the mountains.

The fact is there is a hike and walk to suit all abilities in The Berkshires, and you’ll be sure to find a few among this collection that are best for you. All of these destinations also provide stunning views of the fall foliage in the Berkshires.

Enjoy the following hikes in the Berkshires…

Hiking Mount Greylock in Adams:

Mount Greylock has a number of hiking trails up to the summit and includes: the strenuous 5-hour round trip Gould Trail in Adams, the close-by Cheshire Harbor Trail, the easiest and shortest route to the summit tower and a 4-hour round trip, and the longer Greylock in the Round at over 8-hours, and which starts at the Haley Farm parking area on the western flank of the mountain. Many of the hikes on Mount Greylock offer scenic views from ledge lookouts on the ascents, and pass inspiring waterfalls and forest streams.

Though the trails can be strenuous the views make it worth the effort as Vermont, New Hampshire, Connecticut and New York stretch out before you at the peak… and in the fall you’ll be perched above a blazing patchwork of orange and reds as the forests fiery colors extend to the horizon. More trail details on Mount Greylock >>>

Monument Mountain Hike in Great Barrington:

The profile of Monument Mountain is well known in the area and the popular Hickey Trail is a fairly easy 1.6-mile round trip to the summit. Squaw Peak at 1,640-feet is a modest height but provides spectacular views of three states and on the ascent keep your eyes open for dramatic cliffs and Devil’s Pulpit – a rock pinnacle that is the “monument of the mountain.” The Hickey Trail begins on Route 7 in a picnic area in Great Barrington. More information on Monument Mountain >>>

Hiking Mount Everett, Mt. Washington:

Mount Everett at 2,602-feet is one of the taller summits in the southern Berkshires but the hike difficulty is moderate and during the 5.4-mile round trip you’ll get to see several waterfalls, and worth-the-hike views from the peak. The Race Brook Trail starts at a turnout 5.2 miles south on Route 41 from the junction with Route 23 in Egremont. More trails in Mount Everett State Reservation >>>

The Riga Plateau - An Easy Multi-Day Hike:

This is one of the multi-day hikes in the Appalachian Trail portion of The Berkshires and the Riga Plateau is popular as it is mostly easy hiking along a ridge that provides some outstanding views of the surrounding mountains and countryside. The Riga Plateau section runs from the AT parking lot on Route 41 in Salisbury, CT, and finishes at Jug End Road about a mile from Route 23 in Egremont, MA. If you’re feeling ready to push beyond just day hikes then this is a good trip to gain experience in backpacking through this beautiful countryside. More details on the hike and directions >>>

Walking Mohawk Trail State Forest in Charlemont:

If a stroll and natural ambiance is more to your liking then head to Mohawk Trail State Forest where you can map out a 3 mile ramble through some of the biggest trees in the state. Here you’ll find a 130-foot Red Oak, the tallest in New England. The trails leading out from the campground travel through meadows and woods and along paths with towering white pines and a chance to experience some of the best outdoors in western Massachusetts. The forest includes miles of rivers and streams and offers excellent trout fishing, a swimming and picnic area. More details on walks in Mohawk Trail State Forest >>>

Mount Washington State Forest Walks, Mt. Washington:

Mount Washington State Forest includes what most consider the signature waterfall of The Berkshires – Bash-Bish Falls. The falls end in a spectacular gorge which is restricted, but you can drive to a parking area with a short walk to the views. The state forest has a number of superb walking trails through the woods although at times you’ll need to negotiate rugged terrain in this wilderness area. The forest in the fall is magnificent and popular with leaf peppers and photographers who flock to the colors around the falls. More information on Mount Washington State Forest >>>

October Mountain State Forest in Lee:

October Mountain State Forest is the largest state forest in Massachusetts at 16,500 acres, and derives its name from the stunning colors it exhibits in the fall. But this state forest is scenic any season and attracts visitors from nearby Lenox and in the summer Tanglewood who want to experience the outdoors during their stay. Though trails and camp sites are available for avid hikers the forest has a network of paths through its woods that’ll keep the casual walker contented. The forest has a plethora of wild plants and animals to discover. More information on October Mountain State Forest >>>

Monroe State Forest:

Monroe State Forest is located in the northeastern reaches of The Berkshires. As is normal in the forests of this region the terrain can be rugged with deep valleys and steep mountains, and has a cool climate more akin to northern New England. The forest is a transition forest where hardwoods are mixed with fir and spruce. But it also includes one of the most scenic walks in The Berkshires – Dunbar Brook walk.

The walk will take you through hemlock and beech forests along with birch and maples, and because it’s mostly a shady and cool moist forest, moss clings to the hillsides and along the cold streams. Turn around at the wooden footbridge at 0.9-miles at the brook or continue on the path as it follows the stream. The trail starts in the Village of Monroe Bridge across from the picnic area on River Road. More details on Monroe State Forest and trails >>>

Walks in Bartholomew’s Cobble in Sheffield:

One final often overlooked walking destination is a small area called Bartholomew’s Cobble. It’s located in the southwest corner close to the Connecticut border. In its 278 acres you’ll discover trails to interpret, ponds to skirt, paths to explore and hill’s to climb. It also has an informative natural history museum. More details on Bartholomew’s Cobble >>>

Berkshires Lodging Resources:

The Berkshires are full of towns offering accommodation from world-class resorts and spas to bed and breakfasts with just a few rooms and everything in between. Use the resources below to find lodging that is best for you:

For Great Barrington Lodging click here.
For Lee Lodging click here.
For Lenox Lodging click here.
For North Adams Lodging click here.
For Pittsfield Lodging click here.
For Stockbridge Lodging click here.
For Williamstown Lodging click here.