La Grange & Oldham County — Trains Down Main Street, Country Wineries & the Ohio at Westport

Just half an hour northeast of Louisville, Oldham County is a pocket of small-town Kentucky where the pace slows almost the moment you leave the interstate. The day begins in La Grange, the county seat, where the CSX railroad still runs right down the middle of Main Street — freight trains rumble past the storefronts and cafes several times a day, a spectacle that has become the town's beloved trademark. From there the route wanders into the rolling horse country of the Ohio River valley, where a cluster of family wineries pour Kentucky vintages on shaded patios, before ending at Westport, a tiny river hamlet on a quiet bend of the Ohio. It is an unhurried, single-day loop built around trains, tastings, and river views, with a leisurely lunch on La Grange's historic Main Street at its center.