Travel Guide to Long Island’s East End

By Caitlin Hornik

Wine country. Charming villages. Beautiful beaches. These are just a few of the adventures that await you on Long Island’s East End.

What to Know

If in New York City and you hear the phrase “Out East,” chances are it’s in reference to Long Island’s East End. From the Hamptons to the North Fork to Montauk, there is plenty to do and see.

The East End is quite literally surrounded by bodies of water: The Atlantic Ocean on the south shore, the Long Island Sound on the north shore, and plenty of streams, rivers, and bays in between. You’ll also find plenty of wide-open space; a stark contrast to the sky-high buildings of New York City. There’s cleaner air to breathe and certainly a slower pace.

When to Go

April through October will provide the best weather and ample opportunities to partake in East End activities. However, many wineries are open year-round and some even have cozy fireplaces providing the perfect Winter weather ambiance to enjoy a crisp glass of wine! And there is definitely something to be said for experiencing holiday festivities and decor on the East End, especially with a dusting of snow on the ground and a cup of hot cocoa! But if you’re looking to sit outside in the vines, then be sure to plan your trip for Spring, Summer, or early Fall.

How to Get Around

The East End requires a car to get around. If you’re staying in Greenport, East Hampton, Montauk, or Riverhead, you’ll have an easier time getting around on foot in these village towns. But if you’re looking to hop from town-to-town or winery-to-winery, a car or rideshare service is your best bet!

What to Eat

You’ll be able to find an array of delicious foods on the East End. Find a charming American bistro or a fancy Italian restaurant for dinner, but be sure to check out the smaller local coffee shops and diners for breakfast and lunch! There are some incredible bakeries, breweries, and ciderhouses, too!

What to See

Of course, the main attraction for many is the wine country. There are a few dozen to check out on the East End alone! Some of the most well-known include Wolffer Estate, Sparkling Pointe, Raphael, Pindar, Duck Walk, Channing Daughters, Macari, and Bedell. Many wineries offer private tours and tastings. There are also some amazing beaches in the Hamptons and Montauk! Spend the morning on the beach and then tour wineries into the evening hours.

Riverhead, often considered to be the gateway to the East End, is home to the Long Island Aquarium, the Riverhead Outlets, and the Riverhead Ciderhouse. So there’s no shortage of activities there! Be sure to check out the Flanders Duck, too.

Lavender by the Bay is a seasonal attraction with fields in Calverton and East Marion. It’s a great pit stop for a photo opportunity and a spectacular-smelling pick-me-up! Calverton is also home to Splish Splash water park, which is perfect for a family-friendly day of fun in the sun.

The Hamptons have some of the best shopping on Long Island, so if you’re a fashionista, be sure to plan an afternoon out there.

If you make it to Montauk, be sure to visit the lighthouse! It’s one of the top-rated attractions on Long Island.

Tips and Tricks

If you’re planning your own wine tour, be sure to consult a map to plan your route! You don’t want to do the North Fork and Hamptons/Montauk all in one day -- It can make for a logistical disaster. You can explore the North Fork one day, the Hamptons one day, and Montauk another! It’ll leave you with more time to explore each quaint village and attraction.

When packing for your trip, it’s always helpful to bring an umbrella and a light jacket regardless of the time of year. If you’re on the water, it can get chilly at night, so always best to be prepared!

Long Island’s East End is absolutely beautiful and full of life, no matter when you visit.

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