Driving Route 7 through the Massachusetts Berkshires: A Fall Foliage Road Trip

I am a travel writer, but today, I’m not going anywhere. I’m going to tell you about what I see, “dooh, dooh, dooh, looking’ out my back door.” In a phrase, one of the prettiest places in the world.

Millions of tourists agree: The Massachusetts Berkshires are the state’s third biggest tourist destination, after Boston and Cape Cod. Some years, it seems all of Manhattan ups and moves here for the summer, then lingers to enjoy the leaf season.  We’re just over two hours, and a world away, from New York.

In Your Bucket Because….

• In 60 miles you get your choice of a dozen (or more) world-class activities.
• Art? Kayaking? History? Music? Hiking? Biking? Antiquing? Cuisine? No matter how fussy your travel companions, they’ll find something they love.
• Good for: There’s something for everyone here. Especially photographers.

The Berkshires don’t boast a dramatic beauty — it’s more a gentle rolling prettiness of neat farms and green hills. But come autumn, all that changes. Our white-steepled churches (such a cliché, but how else would you describe a white church with a tall steeple?) are set squarely in the middle of our towns, set off by flaming red maples. Our cider and apples and pumpkins and corn are on display at farmstands, and flaxen cattails swirl in the wind along the banks of the Housatonic. It’s all one big cliché. We are the quintessential New England autumn — and Route 7, our main North-South artery — cuts right through it.

Route 7: A Fall Foliage Spetacular

Route 7 runs from Norwalk, on the Connecticut coast, all the way up through Vermont. The Massachusetts section of it is just under 60 miles long.

Start at the southern end, just north of Canaan, Connecticut, and drive through Sheffield, whose stone buildings in the middle of town include music venue Dewey Hall, which has been a Berkshire cultural center for more than 130 years. Continuing on, you’ll pass several antique stores: These are a fixture all along Route 7, but Sheffield and Great Barrington are particularly well-endowed. Don’t expect rube rural pricing here: the area has been thoroughly colonized by sophisticated New Yorkers, complete with stickers that shock, but if you’re an aficionado, you won’t be disappointed in the quality.

But let’s assume you’re here for nature, and turn our attention to the Housatonic River, which runs along Route 7, framed by the Taconic Ridge to the west and the Berkshires Hills to the east. The Covered Bridge in Sheffield is worth the one-minute detour — look for Covered Bridge Lane on the right, about a mile north of town. If you’re up for a day hike, the Appalachian Trail crosses Route 7 in another mile and a half. (Look for white blazes on telephone poles along the highway). You can turn off and park on Kellogg Road, and hit the trail for a stiff morning wake-up climb to the beautiful views at the Tom Leonard Shelter.

Continuing north, Great Barrington greets you with a standard-issue shopping area before you hit the town proper. The plethora of stores, some high-end, belies the town’s small size (population 7,000): Great Barrington is where everyone in this part of the county comes for errands and provisions, and it’s also the center of the South County tourist trade. Once in the middle of town, the stores get quirkier and more interesting. If you stop for a leg-stretch, you’ll find gourmet coffee, a killer candy store, and locally-made (and locally-loved) SoCo Ice Cream. Don’t miss Railroad Street, once the sleazy part of town, now home to hip clothing stores and galleries.

Continuing, Route 7 jogs to cross the Housatonic. I’m sharing my secrets with you, so here’s another: About a mile north of town, detour briefly left on 183 to Taft Farms, a large farmstand, where you might be lucky enough to stumble on a batch of freshly baked apple cider donuts. Back on 7, continue north to the trailhead to Monument Mountain, where Hawthorne and Melville famously met. The climb to the summit takes about 40 minutes; figure 60 minutes there and back, plus pictures and rest time. The reward: a view all the way north to Mt. Greylock. You’ll know you’re there because of the cars in the parking area. After Monument Monument, there are more possible stops at Windy Hill farm (pick-your-own apples) and the popular Ice Glen Trail (Ice Glen Road is to the right just before the train station).

In Stockbridge, Route 7 makes a 90 degree right turn at the Red Lion Inn, famously painted by Norman Rockwell (his eponymous museum is five minutes away on 183, going south). The Red Lion has a formal restaurant, but if it’s lunch time, pop down into the Lion’s Den, its light-hearted sister pub. Or you can try what used to be Alice’s Restaurant (of Arlo Guthrie fame) in the alley off of Route 7 — although it’s not called that anymore. Alice moved.

Continuing north (7 jogs left), you pass the turn-off for Lenox (think Tanglewood, summer home of the Boston Symphony orchestra). When Sweet Baby James was talking about his dreamlike Berkshires, this is what he meant. Lenox has a ton to do and see, from Edith Wharton’s estate to Ventforth Hall, but for leaf peepers, the Berkshire Scenic Railway (take Housatonic Street east to Willow Creek Road) is the best choice, especially if you have kids.

Route 7 continues north past farm houses, fields, and the marshes of the Housatonic floodplain, along with the occasional shopping development.You’ll see the Arcadia Shop on the left: It’s an outdoors store and a bike and paddling outfitter: You can set up kayaking trips with them to explore the Housatonic, or park there and stretch your legs on some of Kennedy Park’s well-marked and well-maintained hiking trails.

Pittsfield announces itself with potholes, but this former GE company town, which has been struggling to reinvent itself for more than a decade, is a good place to stop for a meal break. For burgers and other American staples, Patrick’s Pub in the main square is easy to find and has won “best wings in the Berkshires” contests multiple times.

Detour

From the center of Pittsfield, you can make a detour that forms a loop of the northern Berkshires by turning right onto Route 9. This will take you to Route 8 and the Ashuwillticook Rail Trail, an 11 mile flat path that makes for great biking and leaf peeping. Follow Route 8 north through the Appalachian Trail towns of Cheshire, Dalton, Adams and North Adams (an old mill town, now a funky hip enclave and home to MassMoCa, the leading-edge contemporary art museum). When you get to Route 2, turn left and follow it west to Williamstown to rejoin Route 7.

Mt. Greylock State Reservation

I’m partial to my South County digs, but knowing what lies ahead, I have to tell you I’ve saved the best for last.

Leaving Pittsefield takes you past Pontosuc Lake (Another chance to stretch your legs: Turn left on Hancock Road, and look for signs to Pontosuc Park). Once you’re back on your way on Route 7, you’ll pass the small town of Lanesborough. About a mile north, look sharp because you don’t want to miss the turn-off for Mt. Greylock Reservation.

Turn right on Main, then right on Quarry/Greylock Road, then left on Rockwell, which climbs for several miles to the 3,488 Massachusetts high-point and Bascom Lodge (rustic accommodations at the top of the world; full service restaurant, hiking trails including the Appalachian, which goes right over the summit). To descend, you can continue on down using Notch Road, which brings you to Route 2: Turn right for North Adams or left for Williamstown.  (Check a map: Lots of choices of routes here). If you want the picture perfect vbiew of a New England college town, Williamstown, just south of the Vermont border, is a must-see.

Awaiting Autumn

Route 7 from Great Barrington to Pittsfield was my commute the first few years I lived here, and I could never bring myself to complain about having to drive 45 minutes. I don’t make that drive daily anymore, but as soon as the first chills of autumn begin to bite, I look for excuses to hit the road.

There’s one impatient maple tree on my way to town. Like a bridesmaid who can’t wait to put on her finery and flounce around, she puts on her make-up and colors early, and by the time everyone else shows up at the party, she is bedraggled and unkempt and her lipstick is smudged and her rouge all runny. But she never learns: Year after year, I see her getting ready for fall, as if she just can’t wait.

The nights are getting colder now, and I know just how she feels.

Practicalities

• Without stops, the drive from Sheffield to Williamstown is just under 50 miiles — an hour and 15 minutes.  But you could easily spend three or four days, or a week, stopping at all the attractions along the way.
• Peak foliage usually begins the second week of October and runs for two weeks, with good color a week on either end.
• Throughout the county, there are lots of B&Bs and charming inns. You’ll find chain motels in Great Barringons, Pittsfield, North Adams, and Williamstwon.

Updated January, 2021