It won't be far. Helga and I are both old, and I respect the limitations of age. She burns 93-octane gasoline, and I'm too cheap to spring for much of that. And then there's Kiki; she gets restless restrained in her single seat, and I fancy the wind tickles her ears. I've installed a plywood partition between her seat and the center console to prevent her from stepping on the controls that open and shut her window and operate the emergency flashers. It's like traveling with a two-year-old – which she is.

I've always loved notches – or passes, cols, gaps, saddles, whatever you call them. They're breaks in mountain ridges that otherwise bar our way. The era of American expansion is still part of our national consciousness, so we all know the names of at least a few: Cumberland Gap, Susquehanna Gap, Donner Pass, Cascade Pass. New England is full of them, and I love to imagine the travails of early settlers as they hacked their way – usually following old Indian trails – up and over and through the barriers to imaginary Edens. The roads that follow them today are full of tight twists and turns. So a notch it was to be.

I took a look at the gaps nearest us – Roxbury, Appalachian, Rochester, Middlebury, Brandon – and settled on an anti-clockwise circle that included Smugglers Notch. Mother and I had been through it a few times, and I'd always marveled at how rough a trail it must have been in post-Revolution days. It's choked with house-sized boulders fallen from the cliffs on either side. The glacier that formed it flowed from north to south, scouring the north approach and dumping the refuse on the downstream side. It's been in the news this year because several truckers, probably following the guidance of a GPS and ignoring the signs that ban trucks from the notch road, have gotten jammed between the boulders on the hairpin bends. Irresistible!

Historic, too. Early Vermont, before the days of easy travel, did a lot of business with its nearest neighbor, Canada. Roads crossed the border everywhere (they still do, but now they bristle with cameras and armed guards), as well as Lake Champlain and Lake Memphremagog. Timber, cattle, wool, and whiskey flowed back and forth without hindrance. Canada, of course, was still Great Britain, and we were destined to have yet another war with the Brits; but fine points like that were lost upon frontierspeople.

Lost upon them also was the chaos in Europe, as Napoleon Bonaparte's megalomania bumped up against everybody from England to Austria to Spain and Russia. President Jefferson, unwilling to take sides in the so-called Napoleonic Wars, signed the Embargo Act of 1807, forbidding commerce between America and Great Britain. Life was already hard in northern Vermont; the embargo just made it a bit harder. The only difference was that legal trade had become illegal. And the rough road through the Notch became a lot busier than it had been. In subsequent years the Notch, only two or three nights' hike from the Canadian border, became a popular escape route for fugitive slaves. In 1922 the Notch road was first paved – just in time for the illegal whiskey trade of the Prohibition years.

Kiki and I followed rivers almost the whole way around the circle. We had coffee at the very welcoming Elmore Store, with the lake behind and the mountain beyond. We gassed up in Morrisville; full service, and again friendly and chatty. So far, a perfect early summer day

In Jeffersonville, just before turning onto the Notch road, I spotted people dining outside. They looked happy, so I turned around. The porch was full, but one couple made room for us: a retired double bassist, his English wife, and their huge black Lab. A Reuben, a glass of Sam Adams, and we were off.

Sign after sign reminded drivers not to tackle the notch in a truck. One, facing pointedly toward Canada, read, "Semi Remorque Interdit." Past the ski resort and the still-snowy slopes, the road got serious, and again I wondered how in the world they could have pioneered it. The summit, where I'd hoped to let Helga out a little, was frustratingly bumper-to-bumper with the vehicles of tourists and climbers. Not a lot of Vermont plates. We putted cautiously down the kinked north side, noting the paint scrapes on the rocks.

The transition from winding mountain road to highway felt abrupt. In no time at all, descending toward Stowe, we met the trappings of tourism coming up. We joined the parade headed to Waterbury, and then, disdaining the Interstate, finished our leisurely ride with the lovely Winooski sparkling beside us.