Scenic Driving Tour: Southern & Central Berkshire

Approximately 44 miles

This tour highlights so much of what the Berkshires is famous for – its scenic beauty and it cultural and performing arts venues.

Begin on Main Street in Great Barrington and follow Route 7 North and cross over the Housatonic River to meet Route 23 East. Route 23 East leads to the mountains and wooded terrain often sought by hikers and explorers. Enter the small town of Monterey, where the General Store still operates catering to residents and second-homeowners alike.

From the center of Monterey, turn left onto Tyringham Road and pass by Lake Garfield towards Tyringham. Upon arriving in Tyringham, notice the contrasting architecture; from an artist’s residence and studio to colonial farmhouses.

Continue along the Tyringham Road until it intersects with Route 102 in Lee and turn left onto 102 West. In just five miles, enter the famous Main Street of Stockbridge immortalized through the painting by its’ own resident, Norman Rockwell. The Main
Street of Stockbridge is the place to watch people while relaxing in a rocking chair or on a park bench. Walking in the area invites people to explore an ancient deposit of boulders from the Ice Age and the interesting Sedgewick family plot in the Stockbridge Cemetary.

Opposite the historic Red Lion Inn on Main Street, turn right onto Pine Hill and then left at the fork to Prospect Hill Road. This area reflects the wealth of families from the Gilded Age who selected choice spots to build their 50 room “summer cottages.’

Return to Main Street, turning right onto Route 102 West and follow to the intersection with Route 183 South.

Turn left onto 183 South. Notice the wonderful Berkshire attractions. A scenic ride along Route 183 and the Housatonic River passes through the picturesque villages of Glendale, Housatonic and Risingdale. Soon, the road re-enters the center of Great Barrington, concluding this tour.

If you prefer a pdf of this to take on the road with you then click here.