12 Cool Towns That Make Long Island a Year-Round Star

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Deal Expert, New York
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Thanks to fantastic beaches and celebrity sightings, Long Island easily draws a summertime crowd. The secret, though, is that this island is a compelling destination year-round, with charming villages, historic sights, interesting museums and huge parks.

The best way to explore Long Island is to make a road trip out of it, meandering your way east toward the north and south forks of the island. As you go, expect to see forests and farmland, scenes out of a New England postcard, hip downtown spots and bohemian beach towns. It’s kind of like all the best parts of America on one island.

The “offseason” (fall, winter, spring) is a great time to visit — you’ll save big on the island’s cute hotels and inns, and the island’s many attractions will be less crowded. Here are a dozen spots you don’t want to miss along the way.

Huntington: To Dine For

Driving along the North Shore that hugs the waters of Long Island Sound, you’re passing through the famed Gold Coast of Gatsby-era mansions. In Huntington, don’t miss the stunning Oheka Castle, a sprawling 1920s estate filmed in Citizen Kane and various other projects, which offers mansion tours to the curious.

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Huntington is known as Long Island’s major dining destination, with restaurants offering up dishes from around the world as well as from its own fruitful backyard (think seafood and farm-to-table). The town is also a hub of arts and culture, with The Paramount offering concerts, comedy and other special events throughout the year, and the Heckscher Museum of Art showcasing more than 2,500 pieces by American and European artists dating back to 1534.


Stony Brook: History & Heritage

Long Island is full of Americana throwbacks, particularly in the Three Village area of Old Field, Setauket and Stony Brook. Be sure to check out St. James General Store, opened in 1857 and in business ever since. Here you can find everything from molasses candy to pottery and children’s toys — and weekend visits from Santa in December.

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As you drive along Route 25A, you’ll see signs for Washington’s Spy Trail, in reference to the secret agents who in 1778 spied on the British during their occupation of Long Island. (Check out the AMC series “Turn” for more on that.)

Make your way to Stony Brook Village, where you’ll find high-end boutique shops around a village green, as well as the Jazz Loft, a newly opened museum with hundreds of instruments, diaries and original sheet music from jazz greats.

Down the road from the Village is the Long Island Museum of American Art, History and Carriages, informally known as the Long Island Museum. The highlight of this Smithsonian Affiliate is the nation’s finest collection of more than 100 horse-drawn carriages dating back to the 1700s.

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Port Jefferson: Incredible Sea Views

Prepare yourself for gasp-inducing views as you make your way into seaside Port Jefferson and catch a glimpse of the Long Island Sound and its busy marina. (The “welcome to NY!” sign here is for ferry passengers arriving from Bridgeport, Connecticut.)

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Affectionately known as Port Jeff, the downtown area resembles a New England town, with its whitewashed buildings and restaurant windows open to the sea breezes in the summertime. The Rinx at Harborfront Park offers outdoor roller skating with harbor views from April to August and ice skating from November through March.

Year-round, visitors can check out the Port Jefferson Brewing Company or the Maritime Explorium, a children’s museum. Seasonally, there’s the annual Dickens Festival (Dec. 3 & 4, 2016), which incorporates costumed characters and decorated streets into a celebration of “A Christmas Carol.”

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Mattituck: Taste of Long Island

It’s about this point in the journey that Long Island splits into two forks and the landscape along the North Fork turns to farms, fields and vineyards.

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Here’s where you’ll find Mattituck, in the middle of Long Island’s blossoming wine region. Taste the vintages at some of the North Fork’s 30+ wineries like Bridge Lane Wine or Shinn Estate Vineyards. East End Bike Tours specializes in seasonal 13.5-mile guided tours of North Fork’s wine country, taking cyclists through tree-lined streets and picturesque vineyards – weather dependent, of course.

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Fittingly, to go with all the wine, Mattituck is also home to a certified cheesemonger at the Village Cheese Shop.

Due to its proximity to farmland and sea, the North Fork food scene is getting rave reviews as a food destination. On the drive, you may be tempted to stop at farm stands selling everything from potatoes and fresh eggs to fruits and ducks. At sit-down restaurants, expect menus to include fresh-caught fish and oysters along with traditional staples.


Greenport: A Whale of a Time

Wine isn’t the only thing brewing in Long Island; craft breweries in the region have also gained a huge following. Greenport Harbor Brewing Company, for example, hosts art and music events, plus there’s a full tasting room on the second floor of the original home brewery.

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Greenport started out as a whaling village and still retains this connection to the sea. Yachts are docked along the harbor and the North Ferry transports passengers (and cars) to and from Shelter Island. The storybook village has a community feel as well as lots of shopping, dining and B&B options, plus there’s a carousel for the kids at Mitchell Park Marina.

Check out the seafood and steak at Claudio’s, one of the oldest family-owned and operated restaurants in America, opened back in 1870.


Shelter Island: Quiet Respite

The only way to get to secluded Shelter Island (or, “The Rock” as locals call it) is by car ferry from Greenport or Sag Harbor. Sitting in Peconic Bay between the North Fork and South Fork, this 8,000-acre island is bike-friendly with few cars compared to the rest of Long Island, but keep your eyes peeled for the many deer roaming around.

Nearly a third of the island is home to the Mashomack Nature Preserve, with plenty of walking and hiking trails that are open year-round. In the warmer months, kayaking is also pretty popular here as the water is relatively calm.

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If it’s people-watching rather than bird-watching that’s your thing, grab dinner or drinks at Sunset Beach, where the scene feels a bit more like the Hamptons.


Sag Harbor: Writers’ Retreat

The ferry south from Shelter Island takes you straight to Sag Harbor, on the South Fork. In the 1800s, Sag Harbor was one of the largest ports in the Northeast, and you can still get a sense of that from the leafy streets shading huge homes.

While the downtown is full of upscale shopping, dining and hotel options, it’s got a bit of downtown Seattle hipness to it as well. Sag Harbor has long been known as a retreat for writers, attracting literary greats like James Fenimore Cooper and John Steinbeck, and it still draws a creative crowd. In fact, many of Bay Street Theater’s productions have moved to Broadway and off-Broadway spots.

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Listed on the National Register of Historic Places, The Sag Harbor Whaling & Historical Museum pays homage to the industry that built this town. Looking for live whales instead? Whale-watching tours are available from local companies in the summertime. While you’re waiting, get a lobster roll or fish sandwich at the Dock House, literally a tiny shack on the pier where you can sit and look at the boats.


Montauk: The New (Old) Cool Kid

Montauk Point Lighthouse used to be the focal point for travelers heading out to “The End”, as locals call Montauk — the furthest point east on Long Island. In recent years, the area has upped its cool factor with boutique hotels and high-end restaurants, so stay the night to properly check out the scene.

Park your stuff at upscale places like Montauk Yacht Club Resort & Marina and Gurney’s Inn & Spa and then rent a boat, go fishing or parasailing, or drink a sample or two from the Montauk Brewing Company. Don’t forget to please your Instagram followers with a sunset and a sunrise photo of the historic lighthouse, commissioned by George Washington in 1792.

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Photo by Alissa Rosenberg

The lighthouse is open daily in the summer months and on a varying schedule throughout the year. Of course, you can get dramatic natural shots outside at any point — especially as the sun rises over the ocean.


East Hampton: Meet the Original

There are around 20 hamlets and villages that make up the Hamptons on the East End of the island, but East Hampton is a celebrity in its own right. This town still oozes cool with its celebrity spotting, upscale shopping and destination dining, not to mention its beaches.

But East Hampton is not just massive summer homes and beach chic. Wander around a 16-acre sculpture garden at LongHouse Reserve or explore modern art at the Pollock-Krasner House and Study Center. Or go camping and hiking at Cedar Point County Park. Or discover local history through a visit to Home Sweet Home Museum (dating back to 1720) or while dining at aptly named 1770 House.

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Visitors to the Hamptons in the fall and spring will find many of the perks that make it a destination for the jet set, without the crowds.


Patchogue & Sayville: Welcome Home

It’s time to head west on the South Shore and get a real sense of hometown in Patchogue and Sayville.

A few years ago, Patchogue revitalized its downtown area by incorporating the local arts community. Because of that, an old vaudeville house became the Patchogue Theater for the Performing Arts, which today hosts live performances, films, educational presentations, commercial productions and community forums. For year-round live music, head to Patchogue’s Blue Point Brewing Company (which has the funniest ad campaign) as it features bands in its tasting rooms.

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All through Long Island you’ll find independent shops, galleries and restaurants, as well as some that have branched out beyond their hometown. There’s one well-known name in the Long Island restaurant scene that makes its home on Sayville’s Main Street. Butera’s started 25 years ago and has grown to four restaurants across the island, forging its reputation on generous portions of family-style Italian food.

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Walk off the meal and stroll over to the Long Island Maritime Museum. In the olden days of sailing, with no electronic navigation, many small ships ran aground into Long Island’s barrier beaches, making it a valley of shipwrecks, and the museum’s 14 acres feature exhibits from 18th- and-19th-century shipwrecks to an actual sloop from 1888.


Fire Island: Put it in Park

Fire Island has the most bohemian vibe of Long Island’s many beach communities. Cars are prohibited in most areas. Most people take a passenger ferry from Patchogue, Bay Shore or Sayville, but you can also use private boats and water taxis. There is bridge access at either end with parking for day-use only. While you’re still on the mainland, check out the historic William Floyd Estate. The Fire Island National Seashore includes this former home of a Declaration of Independence signer.

Sailor’s Haven combines a beach with The Sunken Forest, a 300-year old holly forest. It’s the only one of its kind on the East Coast, and guided tours take you along a 1.5-mile boardwalk through freshwater bogs and the swale between the dunes.

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In addition to residential communities, the 32-mile long barrier island is also home to the picturesque Fire Island Lighthouse. Make sure you climb the steps for a great view.

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If only every road trip ended with a walk along a beach.


Ready to go? Hotel rates on Long Island peak in the summer months, so the offseason months are a great time to visit for a good deal. You’ll find the lowest rates when searching for midweek stays.

With additional reporting by Ryan Haase.


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Show 10 Comments
  • Diane

    Sometimes you don’t give a second thought to where you live until you see it through another lens. This reminded me of why I love my island so much. Thanks!

    • Spectator

      When you’ve been away for YEARS and come back, you can’t believe what you missed while you were living there.

  • Tom Nofi

    Great stuff. Were you also aware that Long Island has a second county, called Nassau. Pretty amazing beaches, history and sites there too, from Glen Cove to Long Beach and everywhere in between

  • Joan Bernstein

    Many restaurants and boutiques close for the winter on the East End, or reduce their hours. Take that into consideration as you explore.

  • Sue Boudreau

    Have you visited Bay Shore lately? A beautiful Main Street with 400 hanging baskets plus fabulous acclaimed restaurants, historic homes including Sagtikos Manor where Washington slept, Gardiner Park for walking trails leading to the bay, a relaxing marina for fishing and the ferries for Fire Island make it a great addition to your list.

  • joe vette

    Liking Southold. On the way, stop at Joe’s Crab Shack .

  • Tara

    I hate to be ‘that person,’ but the Three Villages are Stony Brook, Setauket, and Old Field. St. James is part of the Town of Smithtown.

  • Stephanie Plummer

    I love Long Island, it’s where I grew up and will always be my home!

  • Stephanie Plummer

    Babylon is a really quaint town.

  • disqus_zLY0jsDmax

    You forgot Oyster Bay, Long Beach, Locust Valley, Manhasset, Port Washington…