Underrated Towns to Hit on Your Next Long Island Getaway

Long Island, New York is… well, long. It’s 118 miles across, yet most New Yorkers miss a good 75% of it as they barrel down the Long Island Expressway in a rush to reach the Hamptons.

On the way “out east,” as we say, there’s a common misconception that things don’t get interesting until you pass Riverhead, where the island splits into the North and South Forks. But despite its middle-child status, the midsection of Long Island is full of pitstop-worthy destinations, offering up historic New England vibes to the north and sublime beaches and nightlife to the south. (Famous Long Islander Billy Joel differentiates it this way: “Either you date a rich girl from the North Shore or a cool girl from the South Shore.”)

So eschew the Hampton Jitney for your own set of wheels. Slow your roll and enjoy the journey. Here are the best places to visit on this overlooked slice of Long Island.

If you’re looking for charming New England vibes, plan your Long Island road trip along the North Shore. This is, naturally, the best route if your final destination is North Fork. Driving 25A takes you over narrow, curving roads that hug steep hills and provide tantalizing peeks at the water beyond white picket fences and historic colonial homes.

Port Washington
Just north of Americana Manhasset—a miniature Fifth Avenue packed with luxury stores, if you’re into that kind of thing—you’ll find one of the longest downtown strips on Long Island. Here you can trade big-name brands for downhome local joints like Salvatore's, a cash-only coal oven pizza place whose pedigree ties back to both Patsy’s in East Harlem and Grimaldi’s in Brooklyn Heights. Other names that may ring some bells? Vanderbilt, Guggenheim, Hearst, and even Gatsby (this town served as inspiration for East Egg). Spend the day ogling real estate or head to Sands Point Preserve to see castles and the Execution Rocks Lighthouse.

Roslyn
Historic Roslyn manages to impress in just 0.6 square miles, boasting a postcard-worthy town center with a clock tower from 1895 and a grist mill from the 1700s. Start in Gerry Pond Park and tour the village’s protected landmarks by car or foot. At The Roslyn Hotel, a reincarnation of the original My Father’s Place pays tribute to the legendary cabaret club that once hosted then-unknowns like Billy Joel and Bruce Springsteen (though it’s closed right now due to the pandemic).

Oyster Bay
Yes, it’s also a township—and a rather large one that actually extends the width of Long Island—but the hamlet of Oyster Bay is where you want to set your Google Maps. Check out Teddy Roosevelt’s summer White House, Sagamore Hill; walk the mile-long Oyster Bay History Walk, which manages to squeeze 30 historic sites into one loop; or simply wander into the park across the street from the LIRR train station to find your own perfect patch of beach.

Huntington
One of the biggest villages on the Island, Huntington’s streets are lined with an impressive inventory of shops, galleries, and restaurants. You can start with all-day brunch at Hatch, stake out a spot by the fireplace at Honu, or opt for a waterside patio situation at upscale Prime. During non-COVID times, you can catch dinner and a show at The Paramount or see what’s playing at the arthouse theater. For now, take advantage of the excellent hiking trail at Cold Spring Harbor’s park, then reward yourself with a rainbow cookie crumb cake (yes, of Comfortland fame) and apple cider donuts at Sweetie Pie’s on Main.

Northport
This historic little gem has its own answer to Huntington’s live entertainment scene in the John W. Engeman Theater, an intimate venue for Broadway productions. Exposed streetcar tracks are relics of a bygone era when the village was called Great Cow Harbour, a moniker residents love paying tribute to at annual events like Cow Harbor Day. Community life in this waterfront family town centers around Cow Harbor Park, ideal for a picnic of baked goods from Copenhagen Bakery just across the street.

Stony Brook
It doesn’t get much more New Englandy than this whitewashed clapboard village—a pet project of Ward Melville’s who envisioned it as a “living Colonial Williamsburg.” A visit to the Carriage House Museum is more fascinating than you’d expect, and the Avalon nature preserve packs enough delight to live up to its mythical name. Stop by the adorable Robinson’s Tea Room for a heavy dose of Victorian quaintness, or Pentimento for house-made pasta in their garden. But the real-show stopper is the Three Village Inn, which dates back to the 1750s, and its award-winning, reputedly haunted Mirabelle restaurant.

Port Jefferson
Those ferrying in and out of Connecticut can spot Port Jefferson from the water by its distinctive, candy cane-striped smoke stacks. This large but walkable village boasts a Sunday farmer’s market in Harborfront Park through mid-November, and plenty of seasonally focused restaurants like The Fifth Season and Old Fields. You can always count on East Main & Main donuts to have something special on their rotating menu of oversized, over-the-top treats. On the divier side, Tara Inn is a classic old watering hole with cheap eats, while Billie’s 1890 Saloon is another neighborhood favorite, resurrected after a fire by popular demand.

There’s a lot of small-town pride in the villages along the Great South Bay, and for good reason. The superb beaches are smooth, wide expanses protected by barrier island Fire Island (another destination in and of itself) with nary a pebble to be seen. The number to remember here is 27A, which is Montauk Highway and Main Street in turns, and will take you through a scenic multi-village tour once you cross into Suffolk County.

Long Beach
California isn’t the only state with a summertime surf paradise by the name of Long Beach. Planned by William Reynolds of Coney Island’s Dreamland fame, this town not only rocks a 2.25-mile boardwalk and beach, but a fantastic downtown with rousing nightlife on the West End. It’s a community unlike any other on Long Island, where young professionals and creative businesses—see Baked by the Ocean and Blacksmith’s Breads—thrive.

Rockville Centre
A hub for many NYC commuters, this village has some truly beautiful Tudor, Colonial, and Victorian homes nestled in its quiet neighborhoods. It’s inland, but what it lacks in beachfront it more than makes up for with hiking trails and quaint small town touches like the hand-carved, antique carousel in Hempstead Lake State Park. Stop into the Bowery Bar, a carnival and street fair-themed spot with a menu of creative Frankenfood and games in the beer garden outside. A bit more subtle is Cork & Kerry, an elegant speakeasy hidden in a retro Victorian home serving up creative cocktails.

Freeport
Freeport’s claim to fame is the Nautical Mile, a network of restaurants and party bars that line a long canal down into the Bay. Start your tour at John J. Randall Park as you eat and drink your way down to the Woodcleft Scenic Pier. The aptly named Halfway Down can help you pace yourself appropriately.

Babylon
Couples have been posing for engagement photos in Argyle Park since the dawn of engagement photos, and it’s worth a walk around the lovely grounds en route to downtown. But Babylon’s headliner is the 875-acre Robert Moses State Park, whose iconic bridge and lighthouse mark the western end of Fire Island. Not only is it the oldest state park on Long Island, it’s one of the most perfect stretches of sand you’ll find on it. For a quick bite near the train station, Supreme Philly Cheesesteak gives your taste buds a trip out of state before Gino’s Pizza of Babylon, home of the Everything Bagel Crust, brings you right back home again.

Bay Shore
Bay Shore is best known as the gateway to Fire Island, but don’t board that ferry just yet. Over the past few years, this downtown village has been revitalized into more than just a parking spot. Nerd out at Lost Planet Comics, shop student wares at the cooperative Earth ‘N Vessel Pottery Studio, or grab a drink at the pocket-sized, '70s retro bar, The Cortland. At the very least, treat yourself to an exceptional donut at NoFoDoCo—or North Fork Doughnut Company, whose perfect dough has finally arrived up-Island.

Islip
A stroll through this village is short but sweet—especially when you stop at Manhattan Sweets Boutique Bakery for any of their signature rainbow cookie spins, from cupcakes and bars to baked donuts. Just steps away is Teller’s, one of the island’s best steakhouses; Treme, a New Orleans-style music venue; and Oconee Diner, which is boisterously decked out for every season. Nearby, Heckscher State Park has beaches for swimming, wetlands for kayaking, and walking trails for wildlife-spotting.

Sayville
For one of the biggest, baddest, most generously stuffed, garlic-buttered lobster rolls this side of New England, get yourself to Claws Seafood Market, right at the edge of downtown Sayville. Then walk that bad boy off with a stroll down Main Street, browsing shops like Sayville General Store, Madison’s Niche, and Paper Doll Vintage Boutique. Just north of the main drag, you can do a bit of time traveling at Islip Grange, a cool collection of pre-Civil War buildings in an open park that offers a glimpse of Long Island living in the 19th century.

Patchogue
Patchogue’s Main Street is something of a poster child for successful downtown revitalization—once headed toward blight, today it’s a buzzy nightlife district with an impressive catalog of dining options. There’s Tennessee-style barbecue at Bobbique, authentic Colombian food at Gallo, and a rooftop bar at Caribbean-influenced Rhum. Get a taste of Paris with one too many pastries at Mademoiselle Patisserie, or just have one too many at BrickHouse, Long Island’s oldest brewery. Choose between dough-slingers at Delfiore, cash-only Gino’s, or Detroit- and Neapolitan-style Donatina. And down by the water, you can go upscale at Lombardi’s on the Bay or embrace the kitsch of dining on a literal boat at Harbor Crab Co.

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