The historic village of Greenport may be a two-hour drive from the city, but the things you’ll pass along the way will make the time fly, and possibly prompt several pit stops. The stretch known as the North Fork is lined with excellent farm stands, many a vineyard (and tasting opportunities) and some of the best ice cream around. There’s also plenty of water courtesy of the Long Island Sound and Peconic Bay.
As for Greenport itself, there’s something for everyone. The centerpieces of the main green on the harbor are a 100-year-old carousel, and a less obvious camera obscura, which can be entered by appointment. From there you’ll catch the whiff of Aldo roasting his own coffee and making a nearly legendary biscotti. Main Street is lined with vintage stores, the gem here is the Opportunity Shop. The others can be well, a little hip and precious but still fun to browse.
Clustered together a bit off the main drag is a ship building yard with ample texture, the old jail, and the Greenport Brewing Company. Somehow they all fit together. Don’t forget fresh seafood. My rec is the no-nonsense fare at Hook and Net supplied by Alice’s Fish Market, though there are many options to pamper oneself. Last tip: Take a hike.