Easily accessible via Metro North's New Haven commuter route, the genteel town of Old Greenwich has one of Connecticut's prettiest main streets. The Old Greenwich Railroad Station was built in 1894 and added to the National Register of Historic Places in 1989. Grab the makings of a picnic and a coffee to go from Sweet Pea's Baking Company, which is worth the ride from New York City in itself. Hike to the town's best beach, a long narrow strip of sand extending from the southwest end of the neighborhood. Officially it’s called Greenwich Point Park, but some locals still refer to it as Tod’s Point after a banker who once owned an estate there.
4. Tarrytown & Sleepy Hollow