Main Street runs uphill from the Connecticut River through the heart of Middletown, and for most of its length it is lined with 19th-century brick commercial buildings that give it a proper urban scale. The street is longer and wider than most New England main streets — Middletown was once a significant port city and the infrastructure reflects ambitions from that era.
Today Main Street has independent restaurants, a few bars, a bookshop, and the usual mix of services. The student presence from Wesleyan fills the street on weekend evenings and keeps a dozen cafes and restaurants viable. For a city this size, the street has more energy than you might expect, and the concentration of well-preserved Victorian commercial architecture makes it worth walking the full length.