Autumn’s Top Leaf Peeping Drives In The Western Berkshires

While driving through the Massachusetts Berkshires is a joy any time of year, it’s hard to compete with the colorful displays of autumn. The radiant reds, oranges, and yellows that light up the hills and valleys are the best show in the area. Plan to stay a few days at Staveleigh House Bed & Breakfast and you’ll be able to take in several of these terrific drives.Trees with brightly colored red leaves line a narrow road that winds into the distance.

One of the best fall drives to take starts right here in Sheffield. The rolling hills, gently curving roads, and charming small towns make for a delightful outing. Beginning on Route 7, the nearly 48-mile route takes you north through Great Barrington, then west on Route 23 towards South Egremont, and continues on Route 41 to Mount Everett State Reservation. Be sure to stop here and take the short walk to Bish Bash Falls. Continuing on both Route 41 and Route 7, the route passes through scenic little towns such as Ashley Falls, Clayton, and Mill River before bringing you back to our Inn in Sheffield.

Another popular driving loop for fall colors begins in downtown Great Barrington, again starting off on Route 7. This time, you’ll cross over the Housatonic River and join up with Route 23, heading east into Monterey. Turn onto Tyringham Road and continue until it intersects with Route 102 West in Lee. Just 5 miles west on this road is the historic town of Stockbridge, home to the famous Main Street and Norman Rockwell Museum. Do take this side trip and spend some time looking around. When you’re ready to get back on your journey, turn off Main Street back onto Route 102 West and follow it to the intersection of Route 183 South. This final scenic stretch follows the Housatonic River, passing through several other little towns before returning you to Great Barrington.

There are several other notable drives that are a bit further from the Inn. You can either make day trips out of them or enjoy one or more on your way to or from Sheffield.

Mount Greylock Scenic Byway isn’t a long route, but has wow-worthy views. It starts with open farmland in Lanesborough and traverses through the forested Mount Greylock State Reservation and on to North Adams. The highlight is the stunning panoramic view from atop Mount Greylock, the highest point in Massachusetts.

Mohawk Trail Byway was one of the first auto-touring roads in the United States when it opened in 1914. The scenic 69-mile route offers a variety of enjoyment as it meanders through forests, parallels five rivers, passes through historic towns, and provides dramatic views splashed with color.

Jacob’s Ladder Scenic Byway takes you through a peaceful rural setting, seemingly untouched by modern growth. Railroad enthusiasts and history buffs will especially enjoy seeing the Keystone Arches, stone railroad bridges built without any mortar or steel reinforcements, a remarkable engineering feat in the 1840’s.

Honestly, any direction you head from Staveleigh House is a panoply of color this time of year. As a further enticement to visit, check out our Staveleigh House Fall Foliage Special. Stay two or more weekday nights (Sunday through Thursday) now through October and get 25% discount on your reservation (not valid Columbus Day). Call today or book online!

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