Railroad St, Great Barrington

While this street is technically not the city's main thoroughfare, it might as well be. Lined with gorgeous historic buildings and home to some of the city's greatest restaurants (grab a bite to eat at Martin's Cafe for a long, luxurious brunch or breakfast, enjoy pub-style fare and rich desserts at 20 Railroad Street, or go upscale with splendid Italian Allium (formerly Verdura). Nearby club Helsinki, located in the gallery mall parallel to Railroad Street, has great jazz, and the cinema is intimate and warm: a perfect small-town venue. There are also a few boutiques and shops, mostly with a souvenirs/"outdoorsy" theme (ie, mugs with moose and bears painted on them, adarondacks-style flannel), although this street is also home to a toy store and Crystal Essences, an incense-scented New Age book and crystal/incense/etc stop. Hit up nearby Baba Louie's for out of this world sourdough pizza. The highlight of any visit to picturesque, charming Great Barrington.