Great Barrington, Massachusetts

Whether you're a retiree looking to get away from it all, a family seeking a second home for summertime, or a singleton hoping to put down roots, Great Barrington is one of the most scenic towns in the Berkshires, if not in all of America. With a charming, eminently walkable historical district - filled with some of the best dining outside of New York (Allium - formerly Verdura - on Railroad Street is truly exceptional, as is the delectable Babalouie's Pizza and standby Martin's Cafe) and an artsy, slightly bohemian community feel (come to the Berkshires in summertime for a number of highbrow cultural festivals, including theatrical Summer Stock and dance fest Jacob's Pillow). The town is well-stocked with cultural offerings of its own - including live jazz at the Helsinki Cafe, plenty of cinematic venues, and more. A short drive or walk outside of the centre is Guido's - an enormous organic food store that sets the standard for all locavore produce (and a good place to stock up on free samples). Parents will be pleased to note that the Great Barrington area is home to the highly regarded Simon's Rock Early College Programme, as well as Berkshire County Day school.