New York City’s old-moneyed neighbor is continually overlooked. While Greenwich, Connecticut, is primarily thought of as a stolid commuter town, you can take the 50-minute train ride from Grand Central Station and prove the uninitiated wrong: Here in New England’s southern reaches are historic mansions and Revolutionary War sites, unspoiled 19th-century architecture, and a shopping thoroughfare that takes second place only to 5th Avenue. There are things to do in nature, too—don’t miss the beaches near Greenwich Point Park and the birdlife on Great Captain’s Island.
New Yorkers have been coming to southern Connecticut to take a breather for decades, but the town rarely becomes truly crowded. Weather-wise, the best times to visit are spring, summer, and fall, though you can make Greenwich your winter base for western Connecticut ski trips. Spring is a popular time for festivals, including the annual Greenwich Town Party music festival, which takes place in May.
Greenwich is the first stop in Connecticut on Metro-North Railroad’s New Haven Line, making it a good day trip destination from New York. (For those flying in, the closest international airports are La Guardia and JFK, so you will need to take the train regardless.) It’s a roughly 50-minute ride from Grand Central Station in Midtown Manhattan. The Greenwich train station is within walking distance of Greenwich Avenue and the Bruce Museum, whose exhibits cover art, science, and natural history. Travelers looking to explore further afield should get a rental car.
Ask a local where to grab a bite and a nightcap, and they will likely recommend The Ginger Man. The New England-style tavern has a good beer list and classic pub food, and the bar stays open after the kitchen closes. Fun fact: The front door, bar, and other furniture and décor in the interior were salvaged from since-demolished historic buildings around Greenwich.
