Escaping from the city is hard to do when you have a fear of the Long Island Expressway. While I’m only one of two members of my friend group who has her license, I’ve also been mentally limited to side streets since I passed my driving test. My mild phobia of highways had weak roots to begin with—I watched too many movies involving fiery car crashes as a kid—so conquering it only required a bit of initiative to get from point A (Levittown) to point B (Lavender by the Bay) via the LIE.
There was nothing to fear—at least so I thought. The drive to and fro was rather straightforward, especially since having a passenger-side DJ meant I could push the pedal to the metal in the HOV lane. Equally pleasant: the views of cows grazing on rolling farmlands, in-season crops spurting from the ground, and calming waves coming from Long Island Sound. How dare I deprive myself of these delightful sights!
Evidently the rest of New York City has discovered these wonders the same time as I did. A local I met at an unsuspecting farm stand mentioned her neighbors chirping about Greenport becoming the new Brooklyn. I shuddered at the thought, but it logistically makes sense. It’s a straightforward trek from Penn Station (2.5 hours max), there’s plenty of real estate convenient for summer pop-ups, and there’s easy access to two of the most-beloved parts of millennial diets: oysters and wine.
That’s not to say that the maritime village has completely turned into Kings County 2.0. There are still charming antiques shops running up and down Front Street, the early-morning bird-watchers catching glimpses of herons and grebes on Inlet Pond, and the local watering holes pouring arguably Long Island’s best draft beer. Let that lovely mental image—along with these other must-sees, -dos, -eats, and -drinks—get you through the long LIRR ride.
Greenport Harbor Brewing Co.
What goes better with a bay breeze than a cold one straight from the tap? Residing in a former firehouse, this quaint microbrewery dabbles with both traditional recipes (citrusy IPAs, coffee stouts) and more experimental varietals. Recent brews have included a kelp porter and a golden ale made with grapes from local vineyards. 234 Carpenter Street
Little Creek Oyster Farm
Oyster happy hour tastes a whole lot better when your mollusks are sourced from the waters right below your feet. This seaside bait and tackle shack is known for showcasing the wonders that come straight from the Peconic Bay. Grab a picnic table and order a bucket of oysters to shuck yourself—and don’t worry if you don’t know how; someone on staff will be on hand to give you a demo should you need it. You’ll leave with nary a sliced thumb! 37 Front Street
Greenport Gallery Walks
Get a taste of Chelsea on the first Friday of every month between June and December. Nine participating galleries, along with several of the village’s specialty shops, keep their doors open late (6–9 p.m.) for local art lovers to take in the area’s best works at their own leisurely pace.
Be extra cautious when you step foot inside this corner-side ceramics emporium. This crafty shop is filled from floor to ceiling (quite literally) with pottery, plates, jars, vases, and other fragile knickknacks, most of which are shipped straight from Europe. 302 Main Street
Tea and Tchotchkes
The name speaks for itself, but there’s more to this boho boutique than loose-leaf sips and statement-making home goods. A little bit of everything is showcased on the rustic shelves, from succulents growing inside handmade ceramic pots to organic cotton clothes for all ages. You may even run into the official shop pup, Bean, snoozing around the store. 120 Front Street
Lavender by the Bay
Aside from looking like it came straight out of What Dreams May Come, this aromatic family farm, a few minutes’ drive outside the main village, has some serious cred. Its regal English and French lavender fields have appeared in the pages of Vogue and The New York Times, so you’ll feel perfectly trendy going home with a few bunches of dried lavender and floral-tinged fleur de sel from its rustic farm store. 7540 Main Road