The checkpoints of this trip are: Highway 89 to Exit 3, Bethel, Stockbridge, Rochester, Hancock, Bread Loaf, East Middlebury, Middlebury, the Sugar House Restaurant, Dog Team Road, our mailbox.
(Note that New Haven is NOT one of the checkpoints. You're not going up there. The house is much closer to Middlebury than to New Haven.)
The directions below are more lengthy and complicated than they need to be, but are meticulous, and with two people in the car should be easy.
Get on 89 north and stay on it through New Hampshire, and into Vermont about 15 miles or so. As you near the place where you'll exit, on the right you'll see a model-railroad-fantasy Vermont village that can only have been created by Hollywood, or the Vermont Tourist Bureau's "Calendar Cover" department. That's Royalton. Get off at the next exit, which is a few miles away: Exit 3 to Bethel/Royalton.
The exit swings around and comes to a T. Go RIGHT toward Bethel.
At Bethel, you'll have to keep an eye out. As you come into what might actually be called a township (which is to say, houses almost next to each other), the road dips down and there's a kind of three-corners intersecting at a triangular traffic island. You want to bear left and go over the bridge.
When in doubt, head for Rochester. After that, Hancock. Hancock is the only place that you really need to be careful, because you have to make a left onto Route 125, and the center of town of Hancock, where that happens, is (no joke!) about a hundred yards long. By my memory, Hancock isn't really a town at all, but just a few houses and a general store.
This is where the trip will become the leaf extravaganza, with miles of winding mountain roads taking you up and then down the Green Mountains. The Long Trail crosses Route 125 just at the peak, near the Middlebury College ski area ("Snow Bowl").
At the very very bottom of this mountain pass, you'll be coming to East Middlebury, Vermont. Just keep driving straight 'til you can't drive straight no more. That will be Route 7. Turn right toward Middlebury.
Again, keep driving straight until you're forced not to, which will be nearly in front of the large, brick, Middlebury Inn, at which you'll have to take a left to stay on Route 7, and then almost immediately another right.
In front of you will be the most New England church you've ever seen, the white, high-spired, beclocked, Congregational Church. I had Sunday school there when I was very small, but it didn't stick.
Go straight, so that the church passes by on your left. Keep going and in maybe a half mile, you'll go through Middlebury's last stop light. (Don't go through it if it's red. Wait until green. I know it works differently in Boston, but let's try to be culturally adaptive. It's the way they do it in Vermont.) It's by a Mobil station.
Drive on. If you look to your left at the top of the hill, you'll see the college in the distance. (We'll go for a tour later on.) About two miles or so after that stop light, you will pass the "Sugar House Restaurant" sign on the right.
As you go by the sign, look at the odometer. A tad more than .5 miles later you're going to be turning left, on to Dog Team Road. Do not turn at the first left after the Sugar House, that left being immediately across the way from the lone white house out there. No, not there, but a couple hundred yards after that, half way down the hill, is the turn to the left. If you get to the bridge at the bottom of the hill, you've gone too far.
Drive on Dog Team Road, over the little bridge, past the Dog Team Restaurant, very obvious on the left side. (Immediately after that is the once-upon-a-village Church which is now some sort of crafts shop.) Drive past the first mailbox on the left, to the second one, marked "1234." That's my dad's mail box. 1234 Dog Team Road.
There's only one house up that driveway.
Welcome!
It may be a lot easier just to take Route 4 off of Route 89, pick up Route 7 in Rutland, and come north. If you were coming at night, that's what I'd probably recommend, but I promise that the directions I've given you, above, will make for a drive that is positively beautiful and immensely more pleasureable, and no longer, finally. It's the way my family always makes that trip, whether in a hurry or not. As you drive through Rochester (which could only have been conceived by Norman Rockwell), over the Middlebury gap (in peak colors), and past Bread Loaf (no need to argue! It's a resort AND a graduate school!), you'll see why.
I can't wait to see you again. The hot tub will be ready.