Downtown Bennington is more workaday than postcard-perfect, and that is why it is useful. Main Street has cafes, galleries, old storefronts, public art, and enough local traffic to feel like a real town rather than a preserved village.
Use it as the practical base between the monument and the museum. It is also where Bennington's college-town and old-mill-town identities meet, sometimes awkwardly, sometimes with real charm.