Travel Guide: Navigating Long Island's East End, for a summer or a day

Greater East End coverage is funded in part by Peconic Bay Medical Center in Riverhead, providing world-class services to all of Eastern Suffolk County. Because an extraordinary community deserves extraordinary care.

Call it the East End. Or the Twin Forks.

Or split it into the North Fork and South Fork, aka the Hamptons.

Heck, call it Peconic County; you’re sure to find plenty of sympathizers out here — and less folks loyal to the rest of Suffolk County — mainly over what the five East End towns feel is a lack of representation in county government. But we’ll put politics and nomenclature aside, for now.

The East End of Long Island comprises Riverhead, Southold, Shelter Island, East Hampton and Southampton towns. Within these towns you’ll find dozens of historic villages and hamlets, all leading to Montauk on the South Fork and Greenport and Orient on the North Fork.

You’ll also find a curious mix of people, including “natives” who might trace their local ancestry as far back as the 17th and 18th centuries — either as baymen, fishermen, farmers, ministers or tradesmen — living alongside relative newcomers from Manhattan, Brooklyn and other points west. Then there are the newly arrived immigrants, mostly from Central and South America, as well as the uberwealthy summer residents, which include a healthy share of famous people. And of course, the actual natives of Shinnecock Indian Nation in Southampton.

We’d say they all get along swimmingly, but we’d be lying.

But that shouldn’t stop you from staying out of the fray and enjoying a splendid day, weekend, month or entire season “out East,” as many Long Islanders are apt to say. We can help you navigate it all.

Top: A yacht docked in Sag Harbor in 2023. (Unsplash)

The towns

We’re going to put each individual town under the Spotlight here, starting with Riverhead.

Riverhead

Downtown Riverhead is on the upswing, and it’s been a long time in the making. Main Street and the surrounding areas, which includes Polish Town, now not only plays host to the Long Island Aquarium, Hyatt Place and The Suffolk live entertainment venue, but lots of restaurants and breweries, too. It’s also a great spot to take a walk along the Peconic River, with street festivals such as Alive on 25 running every summer.

And that’s just the downtown. Riverhead Town as a whole offers great parks, beaches, and plenty of farms and farm stands for fresh produce, baked goods and pumpkin and strawberry picking, depending on the season, with about a dozen wineries, two distilleries, and the Riverhead Ciderhouse.

Here you’ll also find Splish Splash Water Park, which is seasonal, and the new Scotte’s Pointe adventure park, where you could try your luck at some indoor surfing and much more. All that and a shopping mecca on the strip of boulevard that’s known as Route 58, which includes Riverhead Tanger Outlets.

Southold

Southold Town offers lots of little downtown hamlets for shopping and noshing along the main historic corridor, Main Road, a wonderful roadway for pastoral sightseeing with historic homes and little museums.

The town is also home to Greenport Harbor Brewing Company, and breathtaking Sound beaches with plenty of lodging options in and around Greenport especially, where you’ll also discover a little nightlife as well, with big parties on the water every Sunday in the summer at Claudio’s. Like in the neighboring Riverhead, Southold Town is also home to plenty of wineries, farms and farm stands, with some really renowned restaurants, namely the North Fork Table & Inn.

Southampton

There are several big downtowns and villages in Southampton Town, which in and of themselves could make for a great weekend getaway, namely Westhampton Beach, the Village of Sag Harbor (half of which is in East Hampton Town), Southampton, Bridgehampton and Hampton Bays.

Among them you’ll find dozens of independently owned boutiques as well as big brand-name shops, art galleries, performing arts centers, boutique hotels and bed-and-breakfasts. And all the downtowns are a short drive or even walk from a beach. There’s also vineyards and pumpkin picking, though not as much as on the North Fork.

If you’re coming from points north, you could stop for a photo outside The Big Duck roadside attraction in Flanders. Makes for the perfect home-made postcard.

East Hampton

Long Islander Juliet Esposito at the Montauk Lighthouse. (Credit: Nick Esposito)

There’s plenty of nightlife in the Hamptons, especially if you have some bucks. But the absolute prime spot for the younger crowds right now is Montauk, on the South Fork’s easternmost tip. But Montauk is also a great spot for families, with plenty of dining options, fishing spots, beaches and even affordable places to eat. It’s also home to Montauk Brewing Company.

The other big downtown is in East Hampton Village, a spot for shopping and sipping coffee and enjoying the restaurants. Oh, and bring a bike. The folks out in East Hampton absolutely love their bikes.

Along the bay to the north you’ll find the historic whaling Village of Sag Harbor, which is shared equally with Southampton Town. This is a wonderful place for a stroll, or to head to with your boat on a hitch. It was also the beloved home of famed American author John Steinbeck, and you could even tour the Steinbeck House. If you see him, say hello to Mets legend Keith Hernandez for us.

Shelter Island

Shelter Island is like an island nation, in more ways than one. And the residents here all know one another — almost like kids in a small high school. But they are very friendly and welcoming to visitors. And during the summer, visitors of all stripes pour in, especially along the Crescent Beach strip.

There are some great boutique hotels on Shelter Island, but it makes for a great day drip as well, with the South Ferry boats leaving from North Haven, near Sag Harbor, every 10 to 15 minutes, as this is the shortest ferry ride you’ll ever take in your life. Heading to Shelter Island from Greenport takes a few minutes longer on the North Ferry, but it’s more scenic. Also, there are plenty of excellent restaurants, many of which have been in business for years. Sunset Beach is a youthful hot-spot on summer weekends,

The waterways

Gosman’s Dock in Montauk during a 2021 sunset. Credit: Barry Riela/Unsplash

There are four major bodies of water that surround these two mostly rural appendages to eastern Long Island. There’s the Long Island Sound, which runs along the North Fork’s northern coastline, and the Atlantic Ocean, which runs along the South Fork.

Between the Forks you’ll find what’s collectively and commonly referred to as Peconic Bay to the west — and Gardiners Bay to the east. Then there’s Lake Montauk and Greenport Harbor, along with the Peconic River, whose headwaters start way west, in Brookhaven Town.

No matter where you are in the salt, these are among the most pristine waterways in the Northeast.

The shores of the ocean and Long Island Sound are wonderful places to see dolphins and seals, even humpback whales that feed close to shore year-round. Snowy owls visit the beaches in the winter.

You can fish, canoe or kayak virtually anywhere, including the brackish Peconic River. Then there’s the sailing and the motor-boating, and yachting.

If you can’t get out on a vessel of some sorts, one of the prettiest strips to travel by land for water views is the causeway toward Orient. The sight of the expansive Peconic Bay from the County Road 105 bridge, which runs between Riverhead and Southampton towns, is pretty breathtaking as well.

Or simply climb the Montauk Point Lighthouse to see it all.

Swimming & sunbathing

A surfer at Cooper’s Beach in Southampton. (Credit: Mercedes Reilly/Unsplash)

The Hamptons has a reputation for being pretty exclusive in the summer months. And, yes, there are private and otherwise restricted beaches. But there are plenty of wonderful — and we’re talking among the best in the U.S. — municipal, county and state parks that are open to everyone, though sometimes with an up-charge for non-resident parking. Below are some of our favorites, with consideration of size (we’re favoring larger) and/or ease of access and parking.

Camping

Whether you’re packing a tent or rolling up with a camper or RV, the East End offers sites for camping out that could rival any in the world, with access to beaches, woods, rivers and amenities. We’ve overlooked a few, but these seven are can’t-miss.

Indian Island County Park, Riverhead
Hither Hills State Park, Montauk
Wildwood State Park, Wading River
Eastern LI Kampground, Greenport
Cupsogue Beach County Park, Westhampton
Shinnecock East County Park, Southampton
Montauk County Park, Montauk

Museums & historic sites

The Horton Point Lighthouse and Historical Museum in Southold. (Credit: Facebook)

The East End is steeped in history, as both Southold and East Hampton lay claim to being the oldest English settlements in New York State. (And were at first considered part of Connecticut.) Because of this, there are plenty of historic sites to visit, as well as museums that are both new and old.