Kansas City's oldest commercial neighborhood, Westport dates to 1833 when John Calvin McCoy established a trading post to outfit wagon trains heading west on the Santa Fe Trail. The trailhead itself was here, and the brick buildings along Westport Road still carry the bones of that frontier commercial energy. Today the neighborhood is one of the city's main entertainment corridors: bars, live music venues, and restaurants packed into walkable blocks that stay busy well past midnight.
The daytime scene is more laid-back than the nighttime reputation suggests. Independent coffee shops, vintage clothing stores, and art galleries sit alongside the saloons. Kelly's Westport Inn, housed in a building dating to 1851, claims to be one of the oldest bars in Missouri. On a Friday evening, starting here and working your way through the neighborhood is as good an introduction to Kansas City nightlife as you will find.