Fall Hiking in the Berkshires

Just last week I looked up and suddenly realized summer’s pretty much done. Yep. The days are getting cooler. The nights chillier. The apples are ripe for picking. And it won’t be long until it’s time for one of our favorite fall pastimes – leaf peeping.

There are lots of ways to check out this annual fall extravaganza. But there’s nothing quite like experiencing nature’s changing palette on foot in the quiet solitude of the Berkshire Hills. So why not throw on some hiking shorts, grab your camera and check out our list of can’t miss leaf peeping hikes?

Five Unforgettable Leaf Peeping Spots

1. Mount Greylock

Let’s begin with the granddaddy of Berkshires hiking - Mount Greylock. Located in North County, the Berkshires’ primo natural landmark looms high above the surrounding Berkshire landscape – reaching a peak of 3,491 feet - the highest point in Southern New England. Follow in the footsteps of Thoreau to the summit and you’ll be rewarded with a patchwork of unsurpassed fall color and a sweeping view of five states.

2. Bear Mountain Trail

Move on to one of the longest hikes in the Berkshires - the 10.5-mile Bear Mountain trail. This ambitious, all-day hike winds from Salisbury, CT to Sheffield, MA. Along the way you’ll discover some stunning, panoramic views of South County that are as good as it gets. - especially the spectacular vistas from the summits of Bear Mountain (the highest point in CT) and Race Mountain. Jump on the Appalachian Trail from multiple points if you really want to up the ante.

3. Monument Mountain

Another of the more recognized landmarks in the Berkshires, Monument Mountain is the hotspot for hiking in the Berkshires. Steeped in history and fabled in romantic lore (Herman Melville and Nathaniel Hawthorne once shared a legendary hike with Oliver Wendell Holmes to the summit), the Mountain features three miles of trails that wind through a white pine and oak forest. The 1,642-foot summit -Squaw Peak - comes with spectacular views of three states, as well as dramatic cliffs and the Devil’s Pulpit – the “monument” of Monument Mountain.

4. Kennedy Park

A pleasant surprise just minutes from historic, downtown Lenox. Kennedy Park is a town-owned and maintained hardwood forest that snakes its way through 502 acres of tree lined forest that highlights a virtual smorgasbord of harvest color. Built from a network of old carriage roads, the park offers nearly 15 miles of groomed trails. While there are a variety of terrains, including several moderate climbs, the park’s trails are predominately flat. Easy hiking, small crowds and brilliant colors – that’s what Kennedy Park is all about. Excellent for casual strolling, hiking, mountain biking, horseback riding, even cross country skiing and snowshoeing in the winter.

5. October Mountain

Bordering the towns of Washington, Becket, Lee and Lenox, October Mountain’s 16,500 acres make it the largest state forest in Massachusetts. Forest trails are available for hiking, mountain biking, cross-country skiing, and off-road vehicle use. Trails are suitable for every level of experience, and include the Appalachian Trail. There is a 2.7mile interpretive hike that winds through the Washington Mountain Marsh and showcases the countless varieties of fall colors that can be found throughout the vast forest’s varied terrain.