Small towns in Connecticut—there are as many in the fair Constitution state as there are WASPs in a country club or dollars in a Fairfield County Roth-IRA. An idea exists amongst urbanites and outsiders that each is indistinguishable from the next, that they blur together like a skimmed copy of a J.Crew catalog. Visit one, in other words, and you’ve visited them all. But while a sense of Connecticut cool—class and discretion if not affluence outright, charm in spades, people who are proud of the place from which they come—very much unites them all, no two towns are truly the same. Some are certainly better than others. Some are in the woods, others on the coast. As autumn descends and the cable knit cardigans come out to play, it might just be time to pay one a visit. But, dear reader, which will it be?
Narrowing down just one Connecticut town to visit for a day trip or weekend away might feel a bit daunting despite the state’s small geographic size. Fear not, Condé Nast Traveler associate editors Charlie Hobbs and Hannah Towey grew up in New Cannan and Norwalk respectively, the two Fairfield County entries on this list, and consider themselves experts in the Connecticut cool category. During their travels across the state, they’ve happened upon the best warm-butter lobster rolls in the country (which, they will argue, are superior to Maine’s mayonnaise-based counterpart), world-class art and architecture hidden in unassuming places, cozy book stores and antique shops, quaint seaside villages, and gorgeous historic homes that will make you rethink every past affront you’ve aimed toward the white picket fence suburbs.
One rustic, unpretentious entry inspired Gilmore Girls, and its Stars Hollow setting in particular. Others have reputations for being upscale, socially impenetrable, totally aspirational. Greenwich, Connecticut’s panhandle entry point, is not on this list not because it isn’t our favorite place—consider a stay on the water at the Delamar Greenwich Harbor on your way out further—but because you can get more Connecticut the deeper you go. Read on for our list, which, as a numbered round-up on the internet, is subjective and limited to the writers’ immaculate (but personal) taste.
