Explore the Village
History is all around you in Greenport—the village is 180 years old. It’s also tiny (just a little over 1.2 square miles) making it ideal for exploring on foot. Make sure you stop by the Antique Carousel, the Camera Obscura and the 1840 Schoolhouse Museum.
Sip Some Beer
You can’t go wrong with any of the beers served up at Greenport Harbor Brewing. The Berliner Weisse-style Days Like These has hints of citrus that will remind you of the warmer months long after the season is gone, while the eccentric Cuvasion is a Belgian-style ale series made with local grapes. Join them for a beer tasting and try them all for yourself.
Explore Some Lighthouses
Go on a lighthouse cruise and step inside the Bug Light, one of only a handful of offshore lighthouses that allows visitors. Or, if your interested in spending time on the East End's water, check out Lighthouse Marina for wakeboarding, tubing or a relaxed day of cruising.
Shop ’Til You Drop
Full of quaint shops, Greenport is an easy place to spend an entire weekend shopping. You’ll find everything from jewelry boutiques to stores where you can stock up on treats for your dog. Don’t miss Beall & Bell, an antiques and home furnishings haven that’s a favorite of interior designers.
Time For Some Eats
Start your day with a raisin scone at Bruce & Son, shuck your own oysters by the bucketful at Little Creek Oyster Farm and make sure to have a lobster roll from Greenport's famous Claudio’s. Looking for something a bit more filling? Dine on casual Italian fare at chef Frank DeCarlo’s (of NYC’s Peasant and Bacaro) Barba Bianca.
Make it a Beach Day
Not that you’d ever get tired of the surf in the Hamptons, but sometimes you just want a beach where you can swim in calming waters. Fifth Street Beach and Park is the perfect spot to enjoy a day of sun and a picnic.
Make Your Own Booze
Not that you’d ever get tired of the surf in the Hamptons, but sometimes you just want a beach where you can swim without worrying about your bikini top getting knocked off in the waves. Fifth Street Beach and Park has calm waters, a dock for dangling your feet and a grassy area ideal for a picnic.
Stay For a While
Not quite ready to say goodbye to lovely Greenport? Cozy up at the dreamy Lin Beach House, a recently restored Victorian hotel or the quaint Wells House Bed & Breakfast. Another favorite is the Arbor View House Bed & Breakfast, located in East Marion.