Fall in the Berkshires

Hilltop Orchards, home to Furnace Brook Wintery, is in Richmond, MAThe natural beauty that dazzles us on a crisp, blue-sky autumn afternoon is the very same beauty that enticed settlers to the area to homestead, to start farms, and build communities.

There is no better way to immerse oneself in the glorious autumn foliage of the Berkshires than a road trip. An afternoon spent traversing the scenic byways of the Berkshires, reveling in the bright displays of leafy color, can easily segue into apple picking or a shopping spree in one of our vibrant communities, where the past is valued and the future is embraced.

Awe-inspiring Color

In the Berkshires, there are several routes that are especially dramatic and well worth the trip. Start on the Mohawk Trail along Route 2 near Clarksburg, a route that includes the famous Hairpin Turn and magnificent view of extraordinarily vibrant foliage. Drive through Williamstown (a quintessential New England college town, with historic brick buildings and classic white churches) and turn south on Route 7 for views of farms and orchards nestled along a picturesque valley. Cloud formations cast moving shadows on the soft hills that rise to the right and left of the road, and there are several places to pull over, stop the car, and drink in the quiet beauty.

Choose to motor south on Route 8, from North Adams to Mount Greylock, at 3,491 feet, the highest peak in Massachusetts. From Lanesborough, take the winding road to the top of Greylock for a spectacular display of foliage, golden yellow to blazing orange to vivid scarlet. Bascom Lodge offers delicious family-style dining and comfortable lodging in the rustic structure at Greylock’s peak, and there are options for hikes (including a section of the Georgia-to-Maine Appalachian Trail) and walks as well through the end of October.

Continuing south and west, Route 41 winds through Richmond and West Stockbridge, past open fields and pastures, wooded lots and family farms. Or choose Route 183 between Lenox and Stockbridge, meandering between stately trees shading the road, and then coming around a bend to a spectacular view of the Stockbridge Bowl, also called Lake Mahkeenac.


Average Temperatures

  • September 65°F
  • October 54°F
  • November 44°F


Discover Our Heritage

A road trip through the Berkshires is an ideal opportunity to indulge a fascination with history, and a visit to Mission House in Stockbridge is an excellent place to begin. The circa 1742 home and garden interpret the days of Colonial Stockbridge when the site boasted both English and Mohican residents.

Traveling south through Great Barrington and then towards Sheffield, there are many notable destinations for history buffs including the Ashley House a house museum dating to the eighteenth century, where visitors can learn the inspiring story of Elizabeth Freeman, a slave who sued for and won, her freedom in 1781. On the Sheffield-Egremont Road, just at the border between the two towns, stand the modest monument to the last Battle of Shays’ Rebellion, on February 27, 1787.

Bring the Berkshires Home

Browse at one of the several fine independent booksellers in the county, or delight in the shelves of enticing playthings at one of the area’s independent toy shops. For the dedicated antique collectors, there are many fine dealers, with clusters of shops in Sheffield, Great Barrington, Lenox, Lee, Pittsfield, and Williamstown. Savvy collectors will find exquisite china and crystal, either a single perfect piece of an array of gleaming place settings; handcrafted weathervanes with a whimsical air, rescued from New England barns; or beautifully build Shaker furniture, still to be found in the region where it was originally crafted. Discover a first-edition of a great American novel or an elegant Queen Anne highboy while engaged in a fascinating conversation with one of the many knowledgeable dealers in the Berkshires.

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