On the old highway maps of America, the main routes were red and the back roads blue. Now, even colors are changing. —William Least Heat-Moon
By Peter Mandel '79
Illustrations by Phil
Route 7 used to be red. An old red road.
If you unfold a map it may be hard to see this. Trace its wobbly line through Connecticut, Massachusetts, Vermont.
It’s a U.S. highway, but it doesn’t read like it was ever a road for moving goods or getting where you needed to go. The interstates, the turnpikes, the bigger urban beltways have turned it blue.
I know this because I am whizzing down an all-but-empty stretch between Kent and Canaan, Connecticut. Route 7’s blueness isn’t just in the sky. It’s in the pockmarked asphalt, in edge-of-town soft ice-cream stops, and in the road signs themselves, which tilt to the side or forward in a humble bow to my car.

I twist off the radio—it’s a crackly station—to try and focus on why I’m here. It is July, and I have set myself a challenge:
to explore a good blue road from beginning to end. I find Route 7’s start near Norwalk, Connecticut, and see from the map that Highgate Springs, Vermont, at the Canadian border, is my ultimate goal.
Why Route 7? To revisit the road that ran through my Middlebury memories, and to see what it looks like now. And a friend was just telling me that we New Englanders are like migrating birds. ‘‘You mean those Florida trips?’’ I asked. ‘‘There’s that,’’ said the friend, ‘‘but there are other patterns. Bostonians head for the Cape on vacation, to New Hampshire, or to Maine. People from New York and Connecticut go
to Vermont.’’
I knew there was at least a pebble of truth here. You could tick off a list of towns in Vermont that were named after
Connecticut burgs: Cornwall, Hartford, New Haven,
Waterbury, to name a few.
I began to think Route 7 might be responsible for this Connecticut-Vermont connection. I bought my map. I packed up bug spray and sunscreen. I was off.
Day 1: Connecticut
Route 7 at its start is a patchwork quilt. I follow directions to the start of my road in Norwalk, but all I see are placards for the 43rd Infantry Division Highway. I try asking at a gas station, and it causes an argument. No one has ever heard of the 43rd. ‘‘You’re on Route 7,’’ says the cashier. ‘‘Forget the signs.’’ Sound advice, I would soon discover.
One of the things I wanted to know was how Route 7 grew up here in the first place. What I read in books is this: Roads that blended into Route 7 would have included Indian paths, riding trails, and mail routes. Stagecoaches would have traveled parts of it as would have soldiers and equipment
during the Revolutionary War.
Here in Wilton, New Milford, Kent, the most historic thing I find is this: There aren’t any chain restaurants. My Mazda 3 and I pass local landmarks such as Hamburger Patty’s, Lucille’s Steaks, and Dexter’s Dog House. I ultimately pull in for lunch at Sclafani’s Street Food, which is, as far as I can tell, a school bus that’s been turned into a stand and painted a sharp-looking red, white, and green.
Charlie Sclafani, son of the owner, confirms it was a bus. ‘‘We used to sell out of a Winnebago,’’ he says, ‘‘but this is better.’’ For $2.75, I get the hot dog combo with mustard, fried onions, and sauerkraut. It’s one of the best dressed-up dogs I’ve ever had.
Pushing north into western Connecticut, I turn off the air conditioning and open the sunroof to get a blast of country air. It smells like farms. Farms with cows. It reminds me of Middlebury in the spring.
I find Kent Falls State Park right by Route 7 and walk to its cascades where local kids are using nets to fish. Later, I drive over a covered bridge in West Cornwall just to see what it’s like. The road boards rattle, but the bridge has clever ceiling lights. On the other side: the Wandering Moose Café.
Day 2: Massachusetts
I’m searching for signs again to be sure I’m still on 7. Routes like this one used to be marked with colored bands on telephone poles. Early signs had black numbers on yellow rectangular shields: Odd numbers usually ran north-south and even numbers east-west.
Just as the old New England Route 5 between Albany and Boston was called the Hubway, Route 7’s predecessor, New England Route 4, was New York-Berkshire-Burlington Way according to a 1922 map I dug up. I finally spot today’s familiar 7 North black on white. I’m still on track.
When I reach Great Barrington, I realize why I keep fishing for leftover Sclafani napkins to wipe my brow. According to the Berkshire Bank, it’s 96 degrees. Near Lenox I see medieval jousting and a maypole dance at the top of a grassy hill. It must be the heat. I pull off the road. Turns out there’s no jousting but brightly-colored tents and pennants lead to Inspired Planet, a rustic looking store.
I scratch my head over the notice taped to the door: ‘‘The gallery is usually open every day in the afternoon. Sometimes earlier and often later. Please come again. Meanwhile look through the windows at our fantastic collection.’’
Turns out I’m in luck. The owner, Dudley Levenson, appears. ‘‘Today,’’ he tells me, ‘‘is the first day of our 21st year in this spot. The other stores next door have closed. But I like the quiet.’’ Levenson shows me some stuff that’s for sale: a plaster panther head, intricately-carved Buddhas, basketlike pointy hats. When we get to a gong, he bangs it and deeply bows. I bow back.
Nearing Williamstown, I’m tallying sightings of roadside animals—the giant sculpted type that advertise Route 7 businesses. In Connecticut there were 20-foot wooden bears and a metal rhinoceros. In Massachusetts, I’ve counted two roadside dogs, a swan (for The Swan Snack Bar), and a hand-decorated moose. When I cross into the Green Mountain State I’m hoping for the real thing.
Day 3: Vermont
Southern Vermont turns Route 7 into a freeway for a while but, despite this, the bumps and bigger hills are sparking greater nostalgia for Middlebury.
In Bennington, I find that I can get a glimpse of the famous battle monument from the road (it’s 301 feet tall) and that I’ve got to fill up with gas. I pull into Hemmings Sunoco right in town.
When I go inside to pay, I get sidetracked. I have driven back in time. Here are oil company signs and souvenirs from the 1930s, ’40s, and ’50s. And over here a rack of vintage license plates, real ones, from every state. The store and displays have more to pore over than a museum.
‘‘We used to be just a family-owned gas station,’’ says cashier Chris Andrews. ‘‘But the collection of car stuff kept growing and growing. Now people make a special trip to see it.’’
North of here, I reach a milestone. According to a marker, my car has climbed to 1,504 feet, ‘‘The Highest Elevation of Route 7.’’ In tiny Wallingford (another Connecticut town name), I pass a fountain made by water trickling out of a boot. The boot is held up by a sculpture of a barefoot boy. I stop to ponder its plaque: ‘‘Erected to the Memory of Arnold Hill by His Children,’’ it says without further explanation. ‘‘April 3rd, 1898.’’
Route 7, I decide, is full of mystery. Even better than the boy is the roadside figure in Salisbury in front of Pioneer Automotive. Pioneer’s banner says, ‘‘We Want Your Bizness and That’s No Bull.’’ But its mascot isn’t a bull. It’s an immense gorilla—it must be 40 feet tall—holding up a full-size yellow VW Beetle with one hand. I can only gape in admiration.
Coming into Middlebury, I discover some unfamiliar roadside sights that seem way too fresh and flat, like scenery in a play. Is that a Courtyard by Marriott? I detour into the center of town and sadly note the loss of 1970’s standbys The Alibi, The Rosebud, and Calvi’s. I am certain it will all revert to the hazy landscape in my head as soon as I pass by.
Moving northward, I shake my head at the strip malls found in Shelburne and South Burlington and distract myself by counting nonchain motels. In Middlebury, I’d checked in for the night at The Greystone Motel, which was clean and friendly, though a little cramped. In Chittenden County, I pass The Sky View Motel, The Country Side Motel, The Yankee Doodle Motel, The Ho Hum Motel, The Dutch Mill Motel, The Maple Leaf Motel, The North Star Motel, and (it looks pretty fancy) The Cadillac Motel.
It’s drizzly and late afternoon when I reach Vermont’s northernmost town, Highgate Springs, where there’s a sign for the Canadian border. Three miles to go.
I’m hoping just to duck into Canada for a few minutes to get the feel of it. But, I discover, Route 7 doesn’t go there anymore. The crossing and Customs control is on Interstate 89.
My blue road curls back on itself and ends. Just like that.
When I get out to take a picture of the sign at the road’s end, a U.S. Customs and Border Control SUV comes out of nowhere and screeches to a stop. ‘‘Any particular reason you’re doing that?’’ asks the agent, pointing at my camera.
I start telling him about Route 7. About its history. Back in the days when it was a cart path, I say, or when it was a real red highway you could have crossed into Canada here.
I can see he isn’t interested in the colors of roads.
I apologize for the photo. I get back in the car. I say nothing more.
It is time to begin the slow drive south.
South on 7. South toward home.
Peter Mandel ’ 79 is a regular contributor to the travel sections of The Washington Post and The Boston Globe.