Each fall, the Berkshires are blessed with a cacophony of color. Reds, oranges and yellows cover the mountains and valleys, while light brown grasses touch the vibrant blue sky. As the temperatures dip at night, the colors begin to pop at the higher altitudes (starting now in early September) and work their way down to the valleys. While a fall hike will get you up close to the colors, a relaxing fall foliage drive through the Berkshires of Western Massachusetts is certainly one of the best and most popular ways to catch some of the most beautiful autumn vistas in New England.
While just about every road in the Berkshires has its own, unique fall foliage views, these are some of the more popular stops and lesser known corners combined into a single weekend loop, with adventures along the way.
After a short, two hour drive from New York City or Boston. you’ll arrive in the village of Salisbury, in the northwestern corner of Connecticut, with Berkshire County bordering to the north. From Rte. 44 in the center of Salisbury, turn north onto Factory Washinee Rd., then left onto Factory St. and then bear left onto Mt. Riga Rd. For this section of the journey, you will want a vehicle with a moderate ground clearance, as you’ll encounter rough road at the top of the mountain (any car that is not especially “low” should be fine, so if you have a sports car, bypass this route by taking Rte. 41 out of Salisbury and meet us back on Rte. 23).
Mt. Riga Rd. quickly climbs in elevation through tight corners above a babbling Riga Brook. After climbing for about 3 miles, you’ll arrive at a T intersection. Turn right onto Mt Washington Rd and traverse this high-elevation nook along the border of Massachusetts and New York. You’re at about 2000 feet in elevation for most of Mt. Washington Rd., so the foliage should be popping here before many other places in the region.
When you cross into Massachusetts, Mt. Washington Rd. becomes East St./Mt. Washington Rd. – follow it north towards South Egremont, MA with a left onto N. Undermountain Rd. and then a quick right onto Rte. 23 in South Egremont. You may want to stop for a quick photo of Mill Pond as you approach Rte. 23, as the mountains provide a beautiful backdrop behind the peaceful pond. A stop at any of the shops in the center of South Egremont is also well worth it and is well deserved after your recent mountain top adventure.
Continue on 23 to where it meets Rte. 7 in Great Barrington and turn left (north) through the village. You could spend a whole weekend in this quintessential Berkshire village, but today is about the road. On the north side of the village, you’ll continue straight onto Rte. 41 north towards West Stockbridge. This section of 41 follows the Williams River closely and provides beautiful scenes of yellow and orange-covered branches hanging over a rippling stream.
Rte. 41 meets Rte. 102 in West Stockbridge, where you’ll take a left onto 102 and upon entering the center of the village make a right onto Swamp Rd. north towards Richmond. Upon entering Richmond, take a slight detour off of Swamp Rd. to catch one of the best and lesser-known views in the Berkshires. To get to the overlook, take a right onto Lenox Rd. and then a quick left onto E Rd., following the road up a hill to view point overlooking farm fields and mountainsides. At the crest of the hill there’s a small bench. Pull off in a safe place and enjoy the cool fall breeze, the warm sun and the surrounding views of changing colors, before hopping back into the car. Continue North on E Rd. until it connects again with Swamp Rd. A half mile up Swamp Rd. it’s time for a sweet treat at Bartlett’s Orchards where you’ll find possibly the best cider donut of your life and delicious snacks to fuel your munchies until your upcoming lunch stop.
From Swamp Rd., take Tamarack Rd./Dan Fox Dr. east to its intersection with Rte. 7. If you need another leg-stretcher, stop at Bousquet Ski Area on Dan Fox Dr. for a round of mini golf or a zip line ride.
Back on 7, head north through Pittsfield. On the north side of Pittsfield, Rte. 7 skirts Pontoosuc Lake, which deserves another photo op with clear blue waters surrounded by orange, red and yellow mountains. Or, even better, get out on the water with a boat rental from U Drive Rent-A-Boat.
After a morning of adventure, there’s no better place to enjoy the cool fall breezes and a hearty lunch than on the deck at Ye Olde Forge Restaurant in Lanesboro, a few miles north of Lake Pontoosuc on Rte. 7. Fill up on some of the best wings in the county and a hearty salad bar, before hopping back in the car to tackle Mt. Greylock.
No fall foliage tour of the Berkshires would be complete without a trip up the Mt. Greylock Auto Road. From Rte. 7 just north of Ye Olde Forge, bear right onto N. Main St. and follow signs for the Mt. Greylock State Reservation Visitors Center on Rockwell Road. From the Visitors Center, the road climbs to the summit of the highest peak in Massachusetts for the undisputed best autumn view in the Berkshires. Bascom Lodge and the War Memorial at the summit provide additional opportunities for exploration, before descending north down Notch Rd., to Pattison Rd., to Luce Rd. into Williamstown.
Turn left onto Rte. 2 west towards the village of Williamstown where you can explore one of the most beautiful New England college campuses at Williams College, or explore the newly renovated Clark Art Institute. After discovering the cozy corners of Williamstown, follow Rte. 2 to the western edge of the village where it meets Rte. 7 at the traffic circle and take 7 south to the ‘6 House Pub at the 1896 House Inn. Dinner and drinks are on tap after a long drive up the western edge of the Berkshires. A drink with dinner is okay, as your lodging for the night is a short drive away.
After finishing dinner, follow 7 south and turn onto Rte 43 south (a right) and then a quick right onto Sloane Rd., where you’ll find the Guest House at Field Farm about a mile up on the right. This is one of the most unique lodging experiences in the Berkshires and with limited rooms, reservations are required well in advance, so make sure to plan ahead. Surrounded by open fields and brightly colored autumn forests, make sure to include the Guest House at Field Farm on your Berkshire fall foliage tour.
While you’ll want to stay the whole weekend at Field Farm, an early morning departure to catch the sun coming up over Mt. Greylock from the overlook along Rte. 7 in front of Mt. Greylock Regional High School is well worth the alarm clock wake-up. You can depart after sunrise as it takes the sun a little longer to come up behind the mountains. Have your camera ready!
From the overlook, head north on Rte. 7 back to the Williamstown roundabout, and then connect with Rte. 2 east. Stop at Wild Oats Market for a quick breakfast from their bakery section. Continue on 2 east, which you’ll follow through North Adams, where you’ll quickly climb in elevation to the Hairpin Turn, with its parking area and spectacular views – another photo op.
Follow Rte. 2 (nationally recognized for its fall foliage) all the way into Charlemont, where you’ll meet up with 8A south. You may hear some “ooohs” and “ahhhs” in the car as you approach Plainfield and Hallocksville Pond on 8A. Follow 8A with a right in Plainfield, then a left in Savoy and another right in Windsor towards Dalton. From Dalton, take 8 (without the A) south through Washington and Becket. You’ll be back at a higher elevation here, so the colors should certainly be full in late September.
Continue on 8 south until you meet Rte. 20, which you’ll take west back to Lee. where you’ll connect with Rte 102 towards Stockbridge. In Stockbridge, stop for lunch at the Lions Den at the Red Lion Inn and enjoy a relaxing post-lunch afternoon on the Inn’s front porch, overlooking the changing colors along Main St.
This is the unofficial end to your weekend fall foliage tour of the Berkshires. If you came from the south, you can follow Rte. 7 back through Great Barrington and into Connecticut. Points east, west and further south (like New York City) can easily be accessed by hopping on I-90 via Rte. 102.
Whether you decide to take this tour or chart your own, there is no better place to explore fall foliage than the Berkshires of Western Massachusetts. Hit the road with a map (or GPS) this fall to discover the views, farm markets and cozy inns that make autumn in the Berkshires a season not to be missed.