The Oregon Trail

East of Westfield, US-20 trucks through cherry orchards, vineyards, and dozens of U-pick fruit stands before ebbing into the center of neatly maintained Fredonia (pop. 10,639), possible namesake for the Marx Brothers’ beloved Duck Soup homeland. Site of the first natural gas well in the United States (1821), Fredonia was also—ironically, for a town in the heart of the western New York Wine Belt—the home of one of the earliest chapters of the Women’s Christian Temperance Union.

Downtown Fredonia boasts the gracefully shaded New England-style town square, bordered by a restored opera house and a host of Greek Revival, Italianate, Victorian, and Gothic 19th-century commercial buildings. A stroll down tree-lined Central Avenue to the north of Main Street (US-20) reveals an equally diverse array of turn-of-the-20th-century homes, which stand in marked contrast to the sterile modernity you encounter up the road in the several I. M. Pei-designed buildings that define the State University of New York (SUNY) Fredonia campus.

The veranda-fronted White Inn (52 E. Main St., 716/672-2103, $75 and up) has been open so long it still boasts of recommendations by 1930s road-food writer Duncan Hines.

East of Fredonia, the vineyards vanish, replaced by the thick stands of scruffy pine trees, used car lots, and cheap-cigarette stands that crowd the roadside along US-20’s two-mile passage through the northeastern corner of the Cattaraugus Reservation.