The Oregon Trail

From inauspicious beginnings in the marshlands and vineyards of the Lake Erie “grape belt” at the state’s far western tip, the portion of US-20 that runs across upstate New York cuts a wide scenic swath through a diverse terrain of flatlands, rippling hills, and spring-fed lakes.

This well-maintained, mostly four-lane road glides surreptitiously through four centuries of history, slicing through vast Dutch patroonships, serene Shaker colonies, blood-soaked Revolutionary War battlefields, Native American hunting grounds, the birthplace of the women’s movement, Underground Railroad hideouts, and the long-calmed waters of the once-mighty Erie Canal. Sparkling baseball diamonds, dairy bars by the dozen, petrified creatures, stately longhouses, abandoned motor courts, prancing wooden horses, off-key nose whistles, and succulent grill-toughened hot dogs are just a few of the countless other reasons to slow down and pull over early and often as you cross the Empire State.

The “Romance Road,” as labeled by a 1940s travel writer, follows several old Iroquois trails as it nudges its way through the western Niagara Frontier, then traces the 19th-century Great Western Turnpike through the Finger Lakes region before easing down into the historically rich Hudson Valley near Albany, where it begins a gradual ascent of the Taconic Mountains and Berkshire foothills that hug the Massachusetts border.

All the way across the state, US-20 roughly parallels the crowded, rumbling I-90 New York Thruway toll road—a necessary evil that lures most of the diesel-spewing, view-obscuring 18-wheel traffic away from placid US-20 with a 65-mph speed limit and the promise of uneventful, predictable fast-food rest-stop dining experiences and fluorescent-lit motels.