This original American colony in New England is sometimes overlooked as a travel destination because of its reputation as a bedroom community for New York. But there is much to recommend in this diverse and charming northeastern state, which contains a wealth of history and geographical diversity within its 5,500 square miles. Yale University and its renowned museums are located in New Haven. The Connecticut River cuts its way through the center of the state. Along the way stand charming colonial villages and old mill towns converted into artsy enclaves. In the southeast, the coast is dotted with towns that still retain the flavor of their seafaring roots. In Mystic, for example, the Independence Seaport Museum features tall ships and a re-created 19th-century maritime village, while Old World charm permeates the horse-farm hills of the northwest.
Westport Cultural Life
Of all the towns that dot the sandy northern shoreline of Long Island Sound, my favorite is Westport (pop. 26,000). Although just 47 miles from Midtown Manhattan, it is a world apart. Paul Newman was the town’s most famous resident until his death, in 2008, but Westport has long enjoyed a connection with the movie, theater and literary worlds. Scott Fitzgerald and his wife Zelda lived here for a while, and the town is thought to have provided part of the inspiration for West Egg, home to the mysterious Jay Gatsby. The Westport Country Playhouse celebrates its 90th birthday in 2021, and the theater has long been a leading off-off Broadway venue, where Stephen Sondheim, among other notables, served an apprenticeship. Today, the Hollywood connection is maintained by resident Ann Hathaway. Although it can be noisy and the prices steep, you can eat good local seafood at The Whelk. And on summer evenings, it is delightful to take a picnic to The Levitt Pavilion for the Performing Arts, an open-air music venue overlooking the Saugatuck River.
New Haven Green
Although the postindustrial outskirts of New Haven are unappealing — the city’s most famous product came from the factory of the Winchester Repeating Arms company — the central 16-acre New Haven Green, home to much of Yale University, is an attractive historic district. The Yale Center for British Art contains a marvelous collection of Turners, Constables and Gainsboroughs (Paul Mellon’s gift to his alma mater). If art appreciation stimulates an appetite, then you might wish to visit Frank Pepe Pizzeria Napoletana, founded in 1925, where they serve the classic New Haven white clam pie.
The Glass House
Across Elm Street from the train station in New Canaan is the visitor transportation area for Philip Johnson’s The Glass House, a modernist masterpiece inspired by Mies van der Rohe’s Farnsworth House in Illinois. Built in 1949, The Glass House was designed by Johnson as his own residence, and it served as his weekend retreat for 58 years. The gallery includes a portrait of Johnson by Andy Warhol, as well as works by Frank Stella, Jasper Johns, Julian Schnabel and Robert Rauschenberg.