Autumn is a magical time in New England,
Full disclosure:
I live in Vermont. Considering that I’m fortunate enough to have a job that allows me to live wherever I choose (within reach of phone service and decent coffee), one might assume I’m here because I like it. Love it, even. One would be right.

So I suppose you should take it with a shakerful of salt when I say that there is no finer place than New England to pack up the car, pull out the map, and put some road beneath your wheels. Just don’t let my bias keep you from doing it, particularly if you can plan a trip during late September to mid-October, when the foliage is at the peak of its annual blaze, elevating an already scenic region to something beyond the scope of human language.

It’s not as if fall foliage in New England is a big secret. In fact, it’s a huge industry, and every autumn, thousands of tour buses and RVs bring hundreds of thousands of leaf peepers to the area. That’s fine; we have plenty of space up here. But if your idea of road tripping is something a little more individual, something tailored to your tastes, then read on.

With only a moderately heightened sense of adventure, a specialized map, and a willingness to let whim be your guide, it’s remarkably simple to plan a route that’ll feel like it was laid out solely for your enjoyment. Using my home-field advantage, I pieced together just such a journey, driving 456 miles in three days. I started in Albany, New York, and meandered through the countrysides of Massachusetts, Vermont, and New Hampshire.

On the following pages, I’ll tell you how my trip unfolded. How yours unfolds is entirely up to you.

The Rules
Without some semblance of order and reason, all road trips run the risk of frivolity and chaos. The beauty, of course, is that you’re the one who decides what the rules are and, perhaps even more importantly, when they should be enforced. Given that every road trip (and road tripper) is different and hence demands a unique set of guidelines, writing the rule book can be almost as much fun as ignoring it.

Here are the rules I created, followed, and, of course, broke.
A. I will stop at least every 50 miles. But not only will I stop, I will get out of my car and talk to someone. Preferably not myself.
B. I will listen to local radio stations rather than tapes or CDs. Local radio stations can lend crucial insight to a region. Or, at the very least, classic rock.
C. I will make at least one unplanned turn each day and follow it for no less than 30 minutes. Then, and only then, may I consult a map.
D. I won’t succumb to road-trip stupor. Distinguished by a heavy feeling of languor, RTS is induced by long hours behind the wheel (see rule A), a steady diet of potato chips, cream soda, and Beer Nuts, and lack of exercise. To help combat this dreaded malady, I will sweat at least once a day. And not by parking in the sun and rolling up all the windows.
E. I will not drive even one mile on an interstate highway.

Day 1
Miles driven:
Best cup of coffee: Lennox Coffee, Lennox, Massachusetts
Road trip epiphany: Windham Hill Road, Windham, Vermont
Rules broken: A, D

Fifty miles after leaving Albany, I roll into Pittsfield, a bustling town of 46,000 situated smack-dab in the Berkshire region of Massachusetts. The Berks (as they’re known) are notable for fine arts, mountains, and quiet villages where homes of stone and white clapboard ring central greens. Pittsfield itself, though not unappealing, is a little lean on the stone/white clapboard/central green mix, so I heed rule C, turning south, rather than north, along my intended route.

Why? I’ve heard that Lennox, just a few miles down Route 7, is quintessentially Berkshire, and I’m eager to see exactly what that means. Turns out, it means pretty much what I’d expected. Thick stone walls line expansive, rolling lawns that brush against the foundations of grand colonial houses sporting — you guessed it — white clapboards.

With my trip odometer pushing 60 (already breaking my own rules, sigh), I roll up to the curb, hop out, and procure a cup of coffee, which I sip while sitting on a bench at the edge of the town green. Besides myself, there are three others on the green: a man in a dress shirt and tie power napping his lunch hour away, and a young couple propped against each other back-to-back, reading thick novels.

Back in the car, I travel north along Route 7. In Williamsburg, I turn east for a short time on Route 2, which leads me to Route 100, and I’m soon traveling through the southern Green Mountains of Vermont. Just before the pavement wends through the town of West Dover, I make my second unplanned turn, swinging right onto East Dover Road. There is no route number; only a small, green sign marks it.

One whim leads to another, and an hour later, having followed East Dover Road along the stony shore of the Rock River, and then Route 30 through the town of Newfane (where the soft grass of the town square almost lures me out of my car and into slumber), I find myself taking a sharp right where 30 bends through Townshend.

There’s no other way to say it: Windham Hill Road is the most beautiful slice of pavement I’ve driven. It climbs steeply for perhaps a mile under a thick canopy of trees before leveling off on a ridgeline where tall, lean white birch form a graceful scrim between road and farm field. There is no other traffic, so I slow to 15 mph, roll my window down, and turn my nose into the scent of leaves and grass and sun. At the far end of the field, a farmer drives his tractor. I wave, but he’s focused on his task and doesn’t see me.

Considering that it takes me four drive-bys to get my fill of the scene, that’s probably a good thing.

Day 2
Miles driven:
Number of Ben & Jerry’s ice cream cones eaten: Too many
Number of “Maple Syrup Sold Here” signs seen: An awful lot
Road trip epiphany: Kristina’s Kitchen, Rochester, Vermont
Rules broken: D

The best part of road trips is finding places no one told you about, places that feel like discovery. I get that feeling at Kristina’s Kitchen, a funky bakery/cafe in Rochester, Vermont, a blink-and-you’ll-miss-it town along Route 100.

First, there’s Kristina herself, a perpet-ually smiling middle-aged woman who looks exactly like the mom you wanted every time your real mother rubbed you the wrong way. I feel this even more deeply when I ask her what kind of bread they have. “Homemade,” is all she says, as if there were no other kinds.

At Kristina’s, where $2 buys me two eggs and two thick slices of toast, I’m invited to share a mottled blue-and-white table with a mother and her teenage daughter. We talk about the weather (of course), Kristina’s coffee (dark and earthy), and the brightness of the yolks that spill from the eggs she gets from a local farmer. “I feel like I’ve met you before,” says the mother. I’m quite sure she hasn’t; Rochester is a long haul from my home. But I can understand why she might feel this way. It’s probably the way everyone feels at Kristina’s.

I continue north through Waterbury, stopping at the Ben & Jerry’s factory for sustenance in the form of mint-chocolate-chunk ice cream, and then, fingers sticky, put my car in gear and wheel back onto the road. The sun is shining, my belly is full of cream and sugar, and the radio’s blasting Tom Petty. Life is very, very good.

Day 3
Miles driven:
Number of dog chapels visited: One
Road trip epiphany: Kingdom Trails, East Burke, Vermont
Rules broken: None!

Morning finds me at The Inn at the Mountain View Farm, high on a ridge above the village of East Burke, Vermont, which is right in the middle of Vermont’s Northeast Kingdom. To understand the Northeast Kingdom, just know this: It’s best to drive very, very slowly up here, for the roads are frequented by moose, farm tractors, and black bears, in approximately that order.

The only sweat I’ve broken in the past two days was climbing the steps at the Ben & Jerry’s factory, so I’ve arranged to meet John Worth just after breakfast (the Inn’s thick buttermilk pancakes, sprinkled with cinnamon and powdered sugar, thanks for asking). Worth is the owner of East Burke Sports, the village’s sole sporting goods shop, and is a co-founder of the Kingdom Trails Association, which has created a trail system more than 100 miles strong. Although the trails are also ideal for walking or running, we opt for mountain bikes and spend the next three hours pedaling through field and forest, up and down steep hills. Worth is 6-and-a-half feet tall, but he flits through the forest like a hummingbird. By the end of our ride, I’m exhausted and entirely purged of guilt.

“I love this place,” I say to Worth as we straddle our bikes at the peak of our climb and gaze into the valley below.

He looks at me as if I’ve just proclaimed a fondness for breathing. “Well, of course you do,” he replies, and pushes off down the hill.

From East Burke, I drive south, connecting with Route 5 in Lyndonville, Vermont. My final destination is Jackson, New Hampshire, but between here and there, perched on a hillside on the outskirts of St. Johnsbury, Vermont, is a place known as Dog Chapel.

Quite understandably, you’re wondering what Dog Chapel is. Turns out, it’s pretty simple: a chapel dedicated to dogs, and in particular, dearly departed dogs. On the steeple, a wooden, winged black lab is in perpetual flight, and the foyer walls are plastered with hundreds of canine photographs and the occasional picture of a cat. Most of these are accompanied by handwritten notes from bereaved human companions. In the chapel proper, the pews are bookended by hand-carved dog statues. Organ music plays softly and sun streams through stained-glass windows.

There’s no one around (at least, no one human or living). Like most boys raised in the country, I always had a pet. It’s been a while since I thought of those animals — a couple of dogs, a cat, one particularly tame pig, and a rabbit — but here in Dog Chapel, I feel compelled to sit for a few minutes and remember. It’s a happy kind of remembering, and I climb back into my car with high spirits.

Soon after, I cross into New Hampshire and drive east on Route 302 into the White Mountains, which are steep and craggy and not a bit white. On this clear day, I can see the 6,288-foot peak of Mount Washington. As I pass into the White Mountain National Park, I can feel my trip coming to a close, my body and mind preparing for re-entry. But I’m not quite ready, so I pull over at the Sawyer River trailhead, shoulder a pack with water and food, and walk into the woods, the leaves crunching beneath my feet.

road signs
rest stops
the mountain top inn & resort

chittenden, vermont
(800) 445-2100 or
always wanted to own a mountain? you can get the same feeling, minus the property taxes, by spending a couple of days at mountain top. located near the dead end of a dead-end road on 345 acres, and overlooking the green mountain national forest and an undeveloped 845-acre reservoir, mountain top offers privacy, luxury, and king of the hill views in spades. activities include horseback riding (they have 35 horses and dozens of miles of trails), hiking, fishing, guided boat tours on the reservoir (bald
eagle sightings are common), skeet shooting, cycling, and … well, you get the idea. the restaurant is excellent, too.

the inn at the mountain view farm
east burke, vermont
(800) 572-4509 or
the restored brick farmhouse that is mountain view is impressively situated on a high ridge, with huge views of the surrounding mountains. the rooms are wonderful; not quite luxurious, but incredibly comfortable, entirely unpretentious, and blessedly absent of television or telephone. the property’s barns (which are exceptionally clean and open to guests) are home to cows, donkeys, and piglets; horses graze the fields. even better, mountain view is at the axis of a 100-mile network of marked and mapped forest paths known as the kingdom trails.

ellis river house
jackson, new hampshire
(800) 233-8309 or
i traded mountain for river at the ellis river house, which is perched on the shores of the (no surprise here) ellis river. of the three inns i visited, this had the most relaxed “home away from home” feel; there is always coffee and tea on, as well as a plate of homemade chocolate chip cookies. they don’t serve dinner, but that’s only because there are dozens of great restaurants in the area. the river house’s breakfast, however, should not be missed.

travel & tourism contacts

(800) 227-6277 or

(800) 837-6668 or

new hampshire:
(800) 386-4664 or

fall foliage hotline:
(800) 258-3608

off the beaten path is one thing; hopelessly lost is another. that’s where delorme’s atlas and gazetteer series comes in. these incredibly detailed state maps will help you connect the dots via little-traveled back roads. they’re mandatory reading for adventurous road trippers. $20 per state. (800) 575-2244 or

detours and directions
ben & jerry’s factory (tours available)

route 100
waterbury, vermont
(802) 846-1500 or

dog chapel
spaulding road
st. johnsbury, vermont
(802) 748-2700 or

east burke sports (bike rentals)
route 114
east burke, vermont
(802) 626-3215 or

kingdom trails association
east burke, vermont
(802) 626-0737 or

kristina’s kitchen
main street
rochester, vermont
(802) 767-4258

massachusetts museum of contemporary art
marshall st.
north adams, massachusetts
(413) 662-2111 or

white mountain national forest (maps, hiking information)
(800) 346-3687 or