The roads upstate—or Down East, as the counterintuitive phrase has it—are smooth, uncluttered, and forested. In fact, for most of this drive, you seem to sail along from one cluster of pretty Colonial houses, one grove of birches (there must be millions of them) or white wooden churches, to another, with no hint of where the locals get their groceries, auto parts, or, mercifully, their fast food.

Day One: Portland to Castine (151 miles)

Barely out of Portland on U.S. 1, stop in Freeport, which is not so much a town as a merchandising vortex. Except for the church and the post office, practically every building has become a factory outlet for some upscale brand. The compulsion to buy seems to grip everyone like some overwhelming gravity: Space aliens landing here would conclude that a shopping bag is part of the human body. Take a lunch break at the Corsican Restaurant, which is near L. L. Bean (the landmark of choice, it seems, in Freeport) and serves great clam chowder and lobster sandwiches (the fare of choice, it seems, in Maine).

Sounds of Ocean Point: the shuffle of shoes on grass, the soft whir of a passing bicycle, the far-off clank of a bell buoy, the sea licking at the weedy shingle at low tide, the mingled, distant mewing of gulls. The moored boats look as if they were painted on the barely tremulous water.

Take the shadow-dappled River Road up the east side of the peninsula to U.S. 1 to Waldoboro, a lovely drive through alternating woods and meadows and past modest old homes sprinkled here and there. The palette of the local housepainters is limited; most houses are white, a few are dark maroon, even fewer are yellow, and one or two the natural silver gray of time-weathered wood. Their gardens are carefully tended, offspring of a short summer, beloved as a child.

Continue on into Castine—call ahead to reserve a room at the Castine Harbor Lodge, a sand-colored inn on a beach full of mussels. The innkeeper, Sara Brouillard, is so casual and unpretentious that you might mistake her for another guest. Her husband, Paul, does a great ahi tuna in the lodge’s waterfront restaurant.

Day Two: Castine to Bar Harbor (216 miles)

Castine seems more conscious of its history than other towns in Maine. Practically every street features one or two historic markers, from which you can learn that this was the first permanent European settlement in New England, and that the irritated natives inflicted tortures upon some of the newcomers. Some of these deeds are described in rather greater detail than you might need. North of Castine, U.S. 1 heads almost due east, a narrow corridor through the pines.

The towns here are small and their outlines are distinct. When you leave one, the transition to woodland is usually sudden and complete. Starting north of Mount Desert Island, things begin to look different—particularly when you hit Ellsworth, a local commercial center that could be anywhere in the United States. Ellsworth recalls the strip-mall development that has blessedly been missing on this route until now. The billboards, burger joints, and convenience stores seem unpleasantly alien.

Follow U.S. 1 to Route 189 into Canada and head toward Campobello Island. There, take a stroll around the grounds of the Roosevelt “cottage,” where FDR summered with his family. Return southward and, if you have time, take 92 to Machiasport. Here, on Machias Bay, you can watch harbor seals lolling on the rocks and study some of the finest Native American petroglyphs in the country. When you finally reach Bar Harbor, stay at the rambling Bar Harbor Inn, some parts like an inn, others a motel. The dining terrace of its Reading Room Restaurant offers a view—a dance of sparkling sun and island-sculpted fog—that is truly spectacular.

Pit Stops

Bar Harbor

Bar Harbor Inn (207-288-3351; www.barharborinn.com; doubles, $75–$319). Reading Room Restaurant (entrées, $19–$35).

Castine

Castine Harbor Lodge (207-326-4335; castinemaine.com; doubles, $75–$150). The Wine Bar at the Castine Harbor Lodge (entrées, $17–$24).

Freeport

The Corsican Restaurant (207-865-9421; entrées, $10–$14).