A Local’s Guide to Greenport

Looking for the perfect fall staycation? Greenport’s got your back.

As Long Islanders, we’re perfectly situated for a variety of staycations. In just a couple hours (traffic permitting), we can be in the mountains, the city or at the beach. One of our absolute favorite local escapes is Greenport—a waterfront town full of great food and drinks, where most everything is walkable.

Where to Stay

AirBNB

👌🏻

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There are only a handful of hotels in Greenport and they are all on the expensive side, not to mention they book up quickly. Our preferred route is to go with an AirBNB. There are so many beautiful homes in Greenport and you can find a location and setup that perfectly suits your group. If you’re with a bunch of people and want to spend time at the beach, there are plenty of options for entire homes on the water. Looking to mostly stay in town for the nightlife? Go with a harbor view apartment right on Main Street.

The Lin Beach House

The team behind Matchbook Distilling Company will open the Lin Beach House this fall. Housed in the huge white Victorian formerly occupied by the Shady Lady, the Lin Beach House will offer 8 guest rooms, the region’s most hyper-local bar, and a true sense of escape. Don’t miss your chance to stay here!

Where to Eat

American Beech

Most of our favorite weekends away start—or end—with a really great brunch. American Beech has a varied menu, so you’ll be pleased whether you’re looking to start your day with raw oysters or an egg sandwich. On our last visit we opted for the shrimp and grits and buttermilk fried chicken—both were rich, delicious and meant to keep you going all day.

1943 Pizza

It may seem odd to travel all the way to the East End of Long Island for pizza, but trust us on this one. What started as a food truck is now 1943 Pizza—a small, cozy spot with a giant brick oven. The menu is small but focused, offerings salads and a handful of small plates in the non-pie category. But you’re here for the well done, fresh out of the oven thin crust pizza anyway. House favorites range from classic margarita to clams casino, with plenty of options to customize your own pie. Note: Call ahead if you have your heart set on going here. They are sometimes closed in the off-season and are always closed on Wednesdays.

Lucharitos

Bloody. Good. Time.

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A taqueria and tequila bar with a bit of a Mexican wrestler vibe, Lucharitos is a fun and casual place to grab lunch or a happy hour drink. Some menu items are expected, like ground beef tacos and chicken burritos, but they also offer lobster nachos, duck quesadillas and a few vegetarian tacos. Wash it all down with a mint watermelon margarita or blackberry lemon mojito.

Little Creek Oyster Farm & Market

Of course we weren’t going to end a list of “where to eat in Greenport” without including seafood. At Little Creek, you can shuck your own fresh oysters. They provide the bucket of oysters, equipment and a brief tutorial and then you go to town. The menu is otherwise limited so we recommend this for a mid-day activity and snack rolled into one.

Where to Drink

Greenport Harbor Brewing Company

Is anything better than a weekend on the North Fork? We're drawing blanks…

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One of the first places that drew us to Greenport was the appropriately named Greenport Harbor Brewing Company. The operation has since expanded to a huge complex in Peconic but the original tasting room and brewery, which occupies an old fire house, still sits right in the heart of Greenport on Carpenter Street. And since they have another facility cranking out year-round favorites like Black Duck Porter and Otherside IPA, the original Greenport Brewery is busy brewing up the OG series—small batch experimental beers like a berry sour Berliner Weisse or an IPA with lactose and passionfruit. You can enjoy your beer in a loft-like setting where local art for sale typically adorns the walls. Note: The Carpenter Street brewery is only open Friday-Sunday, but the location in Peconic is open 7 days.

Brix and Rye

Matt Michel, the man who brought you 1943 Pizza, also owns neighboring cocktail bar Brix and Rye. Though they offer a selection of beer and wine, the focus is mostly on well-crafted cocktails with high quality ingredients. The drink menu changes seasonally though they will always make the classics. The setting is cozy and laid back, plus if you get hungry you can always order a pizza from next door. Note: Again, the hours are a little hit or miss. We have been in Greenport a few times and found they were closed.

Stirling Sake

Sea bass sashimi w/ Komekome sake.👍

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Stirling Sake looks like the Hamptons, feels like Brooklyn and sits right at the edge of Main Street in Greenport. Owner Rick Takemoto and Yuki Mori, former manager of the East Village sake oasis Decibel, are bringing something a little far east to the East End. First and foremost, Stirling Sake is a tasting room. This means an extensive, rotating sake menu, sometimes featuring rarities like wood aged sake. Seasonal flights are available if you just can’t decide, but the menu offers full descriptions and wait staff and bartenders are always knowledgeable. To go with your beverage(s), a menu of small dishes, sushi and noodles is available. We always at least go for the tsukemono (house pickled vegetables) to pair with our sake. Note: They are closed every Wednesday. Tip: The Times Vintage, located right next door, has an impressive selection of men’s and women’s clothing and accessories plus home décor and even some furniture.

Kontokosta Winery

Sound life. Sound wine.

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The wine here is solid, especially the reds, and the setting is beautiful. You can walk out of the barn-like tasting room, across the grounds and be on a bluff overlooking the beach. Not too bad. You can also opt for an “all red” or “all white” flight which is something we wish more wineries would offer. Note: They don’t accept large groups and you also can’t bring your own food.

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Husband and wife team Alicia Valeo and Kevin Breslawski write the blog Beer Loves Company.