The Main Street commercial district is the reason Boonville is on the National Register many times over — the town has more individually listed historic buildings per capita than almost any city in Missouri. The six-block stretch from Spring Street north to High Street is mostly two- and three-storey brick commercial buildings from the 1860s through 1910s, with cast-iron storefronts, painted signs, and a remarkable degree of preservation.
Walk it slowly: notice the limestone foundations cut from the river bluff, the painted advertisements on the side walls (some Coca-Cola murals genuinely date to the 1930s), and the way the street rises and falls with the river bluff. A historic walking-tour leaflet is available at the Friends of Historic Boonville office.