13 Underrated Towns to Explore on Your Next Long Island Getaway

Long Island, New York is 118 miles of small town charm, soft sand beaches, and lively pockets of nightlife. But for most vacationers, about 75% of the island isn’t given a second thought as they plow down the Long Island Expressway on their way to the Hamptons.

The hill we’re dying on? You don’t have to go all the way east to experience an idyllic and worthwhile getaway—plus you’ll inevitably save some coins. We’re here to shed some light on the underdogs of the Long Island ecosystem. From Port Washington’s small business shopping mecca to the engagement photo magnet that is Babylon, the midsection of Long Island is full of road-trip–worthy destinations—despite its middle-child status. Here are 13 of the most underrated towns to explore on Long Island.

Babylon is a romantic destination and the local Argyle Park is a hotspot for engagement photoshoots. If you’re not feeling lovey-dovey, the town is still a beautiful spot to roam around. In fact, the real headliner of the Babylon park system 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 also a near-perfect stretch of sand. For a quick bite, you can’t go wrong with Gino’s Pizza of West Babylon, for pizza, pasta, calzones, and more Italian American classics.

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 handmade wares at the cooperative Earth ‘N Vessel Pottery Studio, or grab a drink at the pocket-sized, 1970s retro bar, The Cortland. At the very least, treat yourself to an exceptional donut at NoFoDoCo (full name: North Fork Doughnut Company), which finally brought its perfect dough up Island.

One of the biggest villages on the Island, Huntington’s streets are lined with an impressive inventory of shops, galleries, and restaurants. Fuel up for the day with an all-day brunch at Hatch or a waterside patio situation at upscale Prime, followed by a sweet treat from Sweetie Pie’s on Main. For a dose of local culture, you can catch dinner and a show at The Paramount or see what’s playing at the Cinema Arts Centre. On the other hand, if Mother Nature is calling to you, take advantage of the excellent hiking trail at Cold Spring Harbor State Park. If you’re looking for stunning lodgings or a historic tour, the Oheka Castle is a non-negotiable.

California isn’t the only state with a summertime surf paradise by the name of Long Beach. Start your mini-vacation off by exploring the 3.5 miles of shoreline and two-mile boardwalk. With the rest of your afternoon and evening, charter a sunset cruise, go paddleboarding, take in the natural beauty of Edwin B. Forsythe National Wildlife Refuge, or hit up Lost and Found or Blacksmith’s Breads for a bite. If you don’t feel like driving, take advantage of transportation packages for a round-trip train ticket on the LIRR, discounted beach access, and free Long Beach bus service.

The historic little gem of Northport sports a live entertainment scene that rivals that of its larger neighbor Huntington. Case in point: John W. Engeman Theater, an intimate venue for Broadway productions. Visitors can catch a wide variety of beloved shows from Footloose to Heartbreak Hotel. Walking around, you might notice the exposed streetcar tracks, which are relics of a bygone era when the village was called Great Cow Harbour—a moniker residents love paying tribute to at the annual Cow Harbor Day. The center of community life can be found at Cow Harbor Park, which is ideal for a picnic of baked goods from Copenhagen Bakery just across the street.

Although technically a hamlet, Oyster Bay is worth an extended stop on your road trip. Highlights on the activity sheet include checking out Teddy Roosevelt’s summer White House called Sagamore Hill, walking the mile-long Oyster Bay History Walk (which manages to squeeze 30 historic sites into one loop), and finding a perfect spot to lounge on Beekman Beach.

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. You can even cosplay a Parisian vacation with a stop by Mademoiselle Patisserie for a French pastry or two. Down by the water, go upscale at Lombardi’s on the Bay or embrace the kitsch of dining on a literal boat at Harbor Crab Co.

Those ferrying in and out of Connecticut can spot Port Jefferson from the water by its distinctive, candy-cane–striped smokestacks. This large but walkable village boasts a Port Jefferson Farmers Market on Sundays in Harborfront Park from May through mid-November, perfect for gathering ingredients for an organic, locally sourced dinner. For a laidback night, Billie’s 1890 Saloon is a neighborhood favorite for cheap drinks and a convivial vibe.

Unlike its neighbor Americana Manhasset—a miniature Fifth Avenue packed with luxury stores—Port Washington trades big-name labels for local, small businesses. Favorites among locals include Eclectic Avenue for crystals and herbs, Locally Inspired for handcrafted gifts, and Port’s Cozy Corner for blankets and candles. Other than shopping, spend the day ogling real estate or head to Sands Point Preserve to see castles and the Execution Rocks Lighthouse.

Just 0.6 square miles, Roslyn does a lot with a little. The postcard-worthy town impresses visitors with its historical landmarks, from the clock tower dating back to 1895 in the town center to the grist mill from the 1700s. Start at Gerry Pond Park for a self-led tour of the village’s protected landmarks by car or foot. In the evening, head to My Father’s Place and pay tribute to the legendary cabaret club that once hosted then-unknowns like Billy Joel and Bruce Springsteen.

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 small businesses like 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.

Long Island
Nestled between the North and South Forks of Long Island is the summer refuge of Shelter Island. Here, visitors will find stellar beaches, wetlands, forests, golf courses, and marinas to perfect for summertime escapades. We suggest you plan some extra time into your day for hiking Mashomack Nature Preserve, playing bocce and sipping cocktails at The Tavern, or picking up some fresh produce from the outdoor farmers’ market at the Shelter Island Historical Society.

The whitewashed clapboard village of Stony Brook epitomizes the New England aesthetic. Here, 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. For a heavy dose of Victorian quaintness, we suggest the adorable Robinson’s Tea Room. But the real-show stopper is the Three Village Inn, which dates back to the 1750s, and its award-winning, reputedly haunted Mirabelle restaurant.

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