7 Best Small Towns in Long Island That Aren’t in the Hamptons

This nautical village toward the eastern tip of the North Fork has an almost New England coastal vibe, with sweeping water views and a tiny but adorable downtown drag. Be sure to pop in for shuck-your-own local oysters at Little Creek Oyster Farm & Market, a beer flight at Greenport Harbor Brewing Company and eclectic sandwiches and snacks (think a grilled tuna banh mi and “redneck Korean poutine”) at Jennie’s at Drossos.

Known for one of the nicest (and cleanest) beaches near the city, Long Beach also boasts a ton of great bars and restaurants, so you can make a day of it even if the weather takes a turn or you’re just sick of the sun. A few faves (though seriously, there are tons): superfood bowls at Island Thyme, burgers and shakes at Laurel Diner and creative small plates at Lost & Found.

Attention, history buffs: This little hamlet is loaded with sites to explore, including Planting Fields Arboretum, a 409-acre estate complete with formal gardens, greenhouses stocked with rare blooms and a Tudor Revival mansion. There’s also Raynham Hall Museum, the 18th-century home of a Revolutionary War spy, and Sagamore Hill, aka the “Summer White House” home of Teddy Roosevelt. And don’t head back to the city without grabbing an Italian ice from a little hot dog stand (and century-old institution) called Bonanza.

This commuter town offers way more than just proximity to the city: There’s the Heckscher Museum of Art, which houses more than 2,000 works by American (and many Long Islander) artists in a gorgeous beaux arts building; the Huntington Harbor Lighthouse, another beaux artsstructure, which dates back to 1857; and the Vanderbilt Museum and Planetarium, a natural-history center inside a sprawling mansion (surprise—this one’s Spanish Revival and designed by one of the firms that did Grand Central Terminal). Stick around for dinner right on the water at Prime and a show at The Paramount.

Another North Fork gem, this teensy hamlet boasts beautiful views of the Peconic, farm stands stocked with local produce and Downs Farm Preserve, a plot of woods and wetlands that includes the site of a Native American fort. But its biggest selling point might be that it’s right smack in the middle of wine country. You really can’t go wrong with any of the nearby vineyards, but we love the sustainable wines and events at Bedell Cellars and the low-key, local’s secret vibes at Lieb Cellars.

If you’re looking for somewhere to really shift into vacation mode, head to the largest town on Fire Island. Along with (duh) a lovely beach, you’ll find plenty of quintessential beach-town shopping and dining options (don’t miss the breakfast items and baked goods at Rachel’sBakery). Be forewarned, though, there are some odd rules here, including no food on the beach and no bike riding in the village—hence its nickname, “The Land of No.”

Nautical vibes abound at this historic maritime village, which has a reputation for attracting artists and writers (Jack Kerouac once lived here). Grab breakfast at Tim’s Shipwreck Diner (the friendly small-town eatery of our dreams), pop into the Northport Historical Society to get acquainted with the town’s seafaring past and stay for a show at the John W. Engeman Theater, where you might catch a few Broadway actors at non-Broadway prices. And you’ll definitely want to spend some time strolling along the harbor, snapping a pic of the iconic gazebo and watching the boats sail by.