Best Scenic Foliage Drives in the Berkshires

Trees with brightly colored red leaves line a narrow road that winds into the distance.

Where are the best scenic foliage drives in the Berkshire? Great question. Fall in the Berkshires is a feast for the eyes. Picture waves of reds, oranges, and golds sweeping across the hillsides painting the forests and mountain slopes in brilliant colors as the leaves put on their annual autumn extravaganza.

Fall foliage season in the Berkshires typically begins in late September and peaks around Columbus Day weekend in October. Warm days and cool, crisp nights spark the onset of the color change, bringing with it a whole host of fall-themed festivals and events that only add to the frivolity of the season. Apple picking and cider sipping certainly flavor the fall, but to truly immerse yourself in Mother Nature’s spectacular fall show a scenic foliage drive is the way to go.

Fortunately, Staveleigh House Bed and Breakfast is ideally situated in the heart of the Berkshires, making it the perfect spot from which to embark on any number of short drives or day-long journeys through the lovely towns and villages that populate our area.

Route 7 North to Williamstown

Starting nearly right outside our doorstep, U.S. Route 7 passes through Great Barrington, Stockbridge, Lenox, and Pittsfield on its way to Williamstown, MA. Clocking in at just a little over an hour, along the route you’ll pass gorgeous vistas, rolling hills and farmlands. In Lenox you may want to stop at the Berkshire Scenic Railway Museum, or visit the Norman Rockwell Museum in Stockbridge. A short detour to Richmond, MA brings you to Hilltop Orchard and Furnace Brook Winery where you can pick some apples, taste some wine and enjoy the beautiful views.

Auto Road to the Summit of Mount Greylock

From the summit of Mount Greylock, the highest peak in Massachusetts, the vistas extend 90 miles towards the slopes of Mount Monadnock in New Hampshire, the Green Mountains of Vermont, the Adirondacks and the Catskills in NY, and Mount Everett in the southern Berkshires. The paved road to the top is steep, but well worth the trip. If you can summons the courage to ascend the 93-foot War Memorial tower via a tightly-wound spiral staircase, the view from the glass orb at the top will take your breath away.

Scenic Mohawk Trail

Although a little bit further afield, a drive along the historic 65-mile byway in northwestern Massachusetts, the Mohawk Trail follows the path used by native Americans as a trade route. The trail passes through several small towns and villages, numerous historic points of interest, and along a portion of the Deerfield River. A truly heartstopping hairpin turn and several smaller loop-de-loops makes the drive fun for the whole family.

Any of these scenic drives will introduce you to the highlights of fall foliage in the Berkshires. But don’t think you have to spend all day in the car to enjoy the beautiful colors of autumn. The blazing foliage adorns the main streets and backroads throughout the region. Book your Berkshires fall foliage trip at the Staveleigh House Bed and Breakfast and don’t forget your camera! You’re sure to get some magnificent photos that we would love to share with other leaf-peepers on our Facebook page.

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