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Hiking the Appalachian Trail in
Connecticut and Massachusetts

By Cliff Calderwood

Hiking in Northwest Connecticut:

The Appalachian Trail touches the northwest corner of Connecticut known as the Litchfield Hills, and The Berkshires region of western Massachusetts.

Though the AT in these areas may not be as rugged and demanding as the sections through northern New England, they nonetheless offer outstanding scenic views and most can be completed in a few hours.

The hills in the northwestern portion of Connecticut arguably offer the best hiking in the state. This area certainly contains the highest points as the Appalachian Trail runs 52 miles through this region from New York to the Massachusetts border.

Hiking the AT can provide many opportunities for multi-day hikes, but for day hikes local towns such as Salisbury, Litchfield, and Torrington are awash in B&B and Inns, and hotels for lodging. This is also a beautiful part of Connecticut to mingle days of mountain hikes with visits to scenic villages and covered bridges. This section of Connecticut is also considered by many to be the antique browsing capital of New England.

Close to the town of Salisbury are three popular hikes; Bear Mountain, Lion’s Head and Prospect Mountain. The 2,316-foot Bear Mountain is the state’s highest peak and an extremely popular hike at the weekend in season. The hike is on the AT and is about 4-hour round trip. The hikes on Lion’s Head and Prospect Mountain rival the scenic views from Bear Mountain but are less traveled portions of the AT, and both are around 3-hour trips.

Connecticut has many short hikes of less than 2-hours that provide families with younger children outdoor activity without being arduous. These include: Breadloaf Mountain near Sharon, Mount Tom in Litchfield, and Cobble Mountain in Kent.

More information on northwest Connecticut here >>>

Hiking in Western Massachusetts:

Similar to its neighboring state to the south Massachusetts’s high peaks are congregated in the western part of the state in the popular vacation area know as The Berkshires ­ this is also the area where the Appalachian Trail cuts through during its 89-mile journey before hitting the Green Mountains of Vermont.

The rolling hills of The Berkshires have long been popular with the rich and famous who stopped going to Newport and building mansions and instead looked for other getaways. Many chose The Berkshires, and it’s this heritage that’s made the region one of the best cultural destinations in New England outside Boston. But people also visit for the scenic landscape and outdoor adventures the area provides.

Hikes on Mount Greylock:
If you’re going to hike in The Berkshires, then sooner or later you’ll want to take in Mount Greylock in the northern Berkshires. At 3,491-feet Mount Greylock is the highest peak in Massachusetts, and provides some of the most strenuous hikes in the region. The AT passes over the summit and interconnects with a number of the peak’s trails.

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. Many of the early literary giants of America found solace and inspiration on this mountain during their summers in The Berkshires. Expect to have plenty of company during the fall months as the mountain and park is a magnet for foliage spotters, or leaf peppers as the locals affectionately call them.

My other favorite hiking destinations in The Berkshires are in its southern Region towards the Connecticut border, and include: Monument Mountain, Mount Everett, and the multi-day AT section of the Riga Plateau.

Monument Mountain Hike ­ Mount Everett Hike:

Monument Mountain in Great Barrington has a summit of 1,640-feet offering dramatic views on three sides, and all for a modest effort of hiking the 1.6-mile fairly easy Hickey Trail. Located in the extreme southwest corner of Massachusetts is Mount Washington State Forest which includes Mount Everett, which at 2,624-feet is among the taller of the hills in this area. If you follow the Race Brook Trail from the state reservation parking area near MA Rte. 41, it will connect you with the Appalachian Trail and take you to the summit. Return the same route for a 5.4-mile 3-4-hour round trip hike.

Hiking on the Riga Plateau:
If you’re looking for a weekend vacation of fairly easy hiking in The Berkshires then consider the 17-mile two-day hike along The Riga Plateau. This is one of Michael Lanza’s favorite hikes in the northeast and he’s seen and done way more hikes on the Appalachian Trail than me, so I trust his opinion. The hike brings together the AT portion running from Jug End at Egremont, Massachusetts through to Lion’s Head in Salisbury, Connecticut. Along the way you scale Mount Bushnell, Mount Everett, Race Mountain, descend into Sages Ravine, hike up Bear Mountain across to Lion’s Head before finishing at the end of Lion’s Head Trail 17-miles later. Apart from the scenic views of the open forests and hills of The Berkshires and the Housatonic Valley there are gentle waterfalls and streams to keep your interest, and campgrounds for your overnight stay.

More details on things to do in Massachusetts here >>>


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