If you’ve ever heard of Long Island, New York, you’ve probably heard of the oh-so-glamorous beaches of The Hamptons. But, I’ll let you in on a little secret: If you skip the socialite shores and keep driving past the final exit on the Long Island Expressway, you’ll find yourself in a mysterious and sleepy town, reserved for only the truest Long Islanders.

What is this magical place?

Welcome to Greenport.

What and Where is Greenport?

Greenport is a Long Island waterfront town that is chock full of historic oddities, fresh fare, and breathtaking views. Located on the north fork of Suffolk County and bordered by the Long Island Sound, Greenport Harbor, and Pipes Cove, Greenport is a tiny, picturesque waterfront village – Perfect for the traveler who is not in the mood for the glitz and glamor of neighboring beachfront destinations.

As a Long Islander who had never been to Greenport, I didn’t know what to think about this mysterious north shore gem, especially on a trip during one of the coldest weeks of the year. But, I’m here to say: Greenport is incredible, even off-season.

From cliffside Chardonnay to the Shelter Island ferry to The Old Greenport Jail, there is something for every type of traveler. Stick with me as I walk you through the top 10 things to do in Greenport, New York!

1. Wine & Waterfront at Kontokosta

Cliffside views and Chardonnay? Yes, please.

Perched atop a cliffside and tucked away at the north end of Greenport, Kontokosta is surely the most underrated gem of all Long Island wineries. Family-owned and managed, Kontokosta’s charm lies in its breathtaking views, intimately stunning architecture, and – of course – its light and pungent selection of wines.

Aside from being a must-do on the list of wine tastings, Kontokosta is also a renowned venue space, perfect for family events, weddings, and more!

Stop by Kontokosta for a tour or wine tasting (walk-ins welcome!). Take in the indoor splendor of the greenhouse-barn-style interior, or stroll to the cliffs and take in the breathtaking ocean views. Take a bottle of Chardonnay home, trust me!

Click to learn more about Kontokosta Winery

2. Dinner and Live Music at First and South

It’s hard to imagine such a quaint and sleepy town also having a lively nightlife, but readers, I must tell you – You have to check out First and South.

Think Brooklyn trendy meets Portland rustic. First and South is the warm and inviting, candlelit mood-setter you’ll need (especially after an afternoon at Kontokosta!). Dine indoors or on the heated patio, while you listen to live music from Greenport’s finest instrumentalists.

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Each day of the week features its own special menu (including the best burrata you’ll ever have!), and there are plenty of options for gluten-free, dairy-free, and nut-free guests.

Stop by for brunch, happy hour, lunch, dinner, or just to hang at the bar. If you’re feeling especially cozy, get the South Street Chowder. Trust me.

Click to learn more about First and South

3. Hop the Ferry to Shelter Island

Sure, maybe you’ve taken a ferry ride before. But, there’s something terribly charming about this ever-so-rustic ferry, not to mention its oh-so-mystifying destination: Shelter Island. For the low price of a $3 token and a 5 minute cruise across the Shelter Island Sound, you will find yourself on a 12-mile seasonal island, populated by quiet residents and overflowing with nautical and historic homes.

With a population of over 3,000 Long Islanders, it sounds like Shelter Island should be a bustling town. But, trust me – Shelter Island (especially in the winter months) is as sleepy as sleepy gets.

Stroll the quiet roads, gawking at the original shutters and wooden shingles of the 18th-century homes. Afterward, grab lunch at Commander Cody’s Fish Shoppe, the local ‘no frills’ seafood joint that is steaming with Long Island favorites.

Just make sure not to stay too long! The Shelter Island ferry doesn’t run all night…

Click to learn more about Shelter Island

Grab a (Gluten-Free) Bite at Crazy Beans

The moment I hear gluten-free pancakes, I’m sold. But, there is so much more to this vintage diner than its mouthwatering menu. From the outside, Crazy Beans might look like your average small-town diner. But, from the moment you step inside, you are overwhelmed with colors, textures, 1950’s memorabilia, and the scent of home-cooked magic.

Located in the center of town, it’s hard to walk by this vibrant delight without stopping in for a bite. Whether it’s for breakfast, lunch, dinner, or just to grab a coffee on a bright red stool, Crazy Beans is the MVP of Greenport diner dining.

Click to learn more about Crazy Beans

Stroll the Shops on Main Street

It wouldn’t be an adorable small-town getaway without exploring the shops, cafes, and boutiques! One of the most interesting parts of Greenport is its town structure. The town center features a lovely mix of colonial homes, restaurants, historic landmarks, vintage shops, and even a gallery!

The vintage shops are definitely a town favorite – On any given weekend, the shops are flooded with residents and tourists alike as they search for furniture, china sets, stamp collections, and more.

Stop by the Nova Constellatio Gallery to marvel at local art installations, then pop into YTQ Thrift for trinkets and long-forgotten finds. End your stroll at Lucharitos for nachos and a beverage of your choice (gluten-free and vegetarian options available!).

The Old Greenport Jail

For the history buffs (and perhaps, paranormal buffs?), you must check out The Old Greenport Jail. Built in 1917, the terribly tiny and spooky jailhouse was in use until the Greenport police department was disbanded in 1947, after a history of scandals!

Walk by after dark, if you dare!

Click to learn more about The Old Greenport Jail

Hop Aboard The Railroad Museum

Excited by the thrill of the rails? You can’t skip The Railroad Museum of Long Island. Created in 1990, the museum has two locations on Long Island (Greenport and Riverhead) and operates under the mission to preserve, restore, and interpret “history and artifacts pertaining to the railroads which participated in the growth of Long Island and its communities”.

Gotta love Long Island pride, right? The Greenport facility is located on the waterfront in the historic 1892 freight house of the Long Island Rail Road!

Visit the museum and marvel at photographs, rail equipment, toy trains, and other historical nods to days gone by.

Click to learn more about The Railroad Museum of Long Island

Dine at Claudio’s Waterfront

It wouldn’t feel quite right to explore a small waterfront town without grabbing dockside dinner, would it? Claudio’s has been in business since 1870 and has undergone many changes and updates over the last 150 years.

The original owner, Manuel Claudio, fell in love with Greenport when the ship he was working on docked in the harbor. Sixteen years later, Manuel relocated to the port town and opened Claudio’s.

Today, visitors can dine and take in photographs of the past century, which charmingly adorn the walls of the interior. Grab dinner indoors or harborside, or grab a drink at the original Victorian Bar, built by Manual Claudio, himself!

Click to learn more about Claudio’s Waterfront

Shelter Island Heights Pharmacy

A pharmacy? Yes, readers, trust me. This is not your average CVS.

Have you ever wanted to travel back in time?

Look no further than this time capsule, nestled on a hilltop in the center of Shelter Island.

From the moment you walk through the doorway, Shelter Heights Pharmacy feels like you’ve fallen through a portal and ended up in 1950s small-town America. With trinkets and remedies and home decor lining the shelves, it’s easy to almost miss the 50s-style counter and pancake griddle, tucked away in a distant nook of the pharmacy.

Sit at the counter and immerse yourself in bacon and egg sandwiches, cheeseburgers, and root beer floats. When you leave the store and are transported back to modern day, you’ll wish you could have stayed longer.

Stop by and have a bite! But, make sure not to be too late… The kitchen closes early!

Click here to learn more about Shelter Island Heights Pharmacy

Ride the Greenport Carousel

Sure, maybe carousels aren’t your thing. But, readers, this is a mysterious must.

The Greenport Carousel, also known as Northrop Grumman Carousel, is located in Mitchell Park in downtown Greenport. With views of Greenport Harbor and Shelter Island, optics from this throwback amusement ride are unmatched.

While this may seem like your ordinary carousel, its origin story is a bit… odd. And by odd, I mean it doesn’t exist. No one knows who built this carousel, but it is said to have been constructed sometime in the 1920s, due to its mechanics and serial number. It is also rumored to have been used in a traveling carnival, due to its ease of disassembly.

The first official record of the carousel was in 1950 when Northrop Grumman purchased it for community events at its Calverton plant. When the plant closed in the 1990s, it was donated and later ended up in Greenport, after much competition from neighboring towns. Today, the Greenport Carousel is a huge attraction for tourists, residents, and families across Long Island.

It’s not every day a carousel with no origin story arrives on your doorstep.

Ride the carousel in Mitchell Park from 10 am to dusk.

Click here to learn more about the Greenport Carousel

Final Thoughts

I had my misgivings about this mystically tiny town, but this citified Long Islander stands corrected! Greenport is filled to the brim with oddities, activities, and mysteries. A few days in this waterfront hamlet didn’t feel like enough, and I find myself daydreaming about my next trip to Greenport at least once a day.

From wineries to mysterious carousels to the best gluten-free pancakes I’ve had in what feels like a decade, I know that Greenport has everything this North Shore girl needs to have an adventure.

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Author Bio: Aurie Ceylon is a writer, reader, and traveler from New York City. A quirky and self-proclaimed wanderer, Aurie writes detailed exploits of adventures on her blog – hey, it’s aurie! 

Aurie is finding happiness through her travel adventures. Stick with this New York wanderer as she fills her heart – and stomach – in small towns across America.

Follow Aurie on Instagram to see more of her travel content! IG: @heyitsaurie