The essential escape for urbanites in New York City, Boston, and Philadelphia, the Berkshires provide world-class foliage viewing alongside notable art and culture.
Narrow winding roads connect mountain hamlets set against a forested backdrop of crimson, yellow, and every hue in between, making for the most beautiful gallery-hopping or antiquing trip of your life. Or, spend the weekend at one of the region’s storied spas, soaking in the sweeping autumn views.
Take a road trip
In the Berkshires, there are several routes that are especially dramatic and well worth the trip. 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.
Of course you should head north and visit 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.
You can 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.
A Fall spa day
Unique among spas, Canyon Ranch Lenox is an all-inclusive health resort and luxury spa. Besides the usual treatments such as massage therapy and yoga, they offer services to prevent illness and treat serious chronic health conditions. Through its Canyon Ranch Medicine center, you can meet with board-certified physicians for tests ranging from diabetes to sleep disorders. If you need a break from a hectic life, this resort-spa offers many fun and relaxing classes such as cooking and metaphysical learning. For the traditionalist, there’s canoeing on an idyllic lake, and when in season, cross-country skiing. Here you can reenergize with fitness classes or soul searching ones.
The Spa at Cranwell is a full-service resort and luxury spa, with facilities ranging from golfing to indoor/outdoor pools and tennis courts. With a menu of over 50 spa services, here is where you’ll find the ultimate experience in luxury spa amenities. Relaxing treatments range from soothing massages to rejuvenating skin and body treatments, including facials, Swedish and deep tissue massages, many beauty salon treatments and more.
Lenox Apple Squeeze: Sept. 23-24
The 38th annual Lenox Massachusetts Apple Squeeze is a long-standing tradition in Berkshire County, ushering in the Fall season.
Join local shops, restaurants, artisans, musicians, farm stands, & performers as Lenox celebrates the apple harvest with a fun & engaging free street festival for all ages.
The Lenox Apple Squeeze has continued to build better entertainment options every year.
This year we have gone out and booked some great music for the Apple Squeeze Main Stage.
With our best lineup ever, The SteelDrivers, Wild Adriatic, Sierra Hull, Billy Strings, Whiskey Shivers, Dwight & Nicole, The Elovaters, Swale, Freevolt and 5 GUN DRAW will give us two days of incredible free music on Sept. 23-24! Stay tuned to learn all the great local acts playing on three Berkshire Exposer stages around town!
On top of that we will again have the Family Fun Zone with games and shows for children, wagon rides around town, a 5k race, Children’s Olympics and much more. The 38th annual Lenox Massachusetts Apple Squeeze is a long-standing tradition in Berkshire County, ushering in the Fall season.