A Night on the North Fork

Where to Lay Your Head on This Side of LI

Named among “America’s Prettiest Towns” by Forbes magazine, Greenport (and neighboring Jamesport) make for a quiet getaway on Long Island’s North Fork. Tucked against the shores of Greenport Harbor, famed Mitchell Park & Marina hosts waterfront activities all year long, and historic homes line the streets.

Nautical buffs will be delighted by the area’s old-world charm – not to mention the East End Seaport Museum – while more adventurous visitors should tour Long Beach Bar “Bug” Light, one of only four offshore lighthouses in the country that receives visitors. For oenophiles, the villages are conveniently located in the heart of the North Fork’s thriving wine country. If you opt to sip a cocktail, imagine the town’s Prohibition-era heritage as a rum- running destination or quietly read some Walt Whitman (he’s said to have taught a semester at Greenport High School). No matter your taste, this quiet coastal paradise is well worth the trip, and here’s where to stay.

Sound View Greenport

Tucked against its own private beach, with sweeping views of Long Island Sound, the aptly named Sound View is an appropriately transportive escape. Cedar-paneled bedrooms offer sweeping views of the water, with optional shared or private decks, and the on-site restaurant, The Halyard, which capitalizes on the region’s freshest seafood and produce. (Don’t miss the classic Lobster Roll.)

For entertainment, there’s Joe’s Pub, a collaboration with Manhattan’s famed theater and cocktail destination of the same name in Greenwich Village; expect world-class acts and potent potables with which to enjoy them. All of which is to say: this is a city-approved beach vacation, complete with all the trappings of the Big Apple, but located 100 miles – and a world of relaxation – away.


Cliffside Resort

Cozy up on a beach chair gazing at the surf, tucked comfortably behind a green dune that separates you from…well, the rest of the world. That’s Cliffside, a decadent destination for Hamptons visitors in search of the ultimate escape. Units range from “water’s edge” to “water view” to “waterside,” with amenities such as complete kitchens with refrigerated wine coolers and high- thread-count Frette linens.

Cast your eyes over the rolling green lawn from your private balcony (don’t worry; they come standard on every condo) and Instagram your vacation via complimentary high- speed WiFi. You’ll do it all in comfort, with individual air conditioning in your room and pool towels, ice, and even beach-side lounge chairs included. Peak-season movie nights are a crowd favorite, but you can also bliss out with yoga and Pilates classes on the lawn.


The Duncan Inn

This self-described “boutique motel” is an enticing hybrid of motor court and resort: casual but comfortable, and nicely situated in the heart of the North Fork’s prestigious wine country. Expecting a crowd? The rooms aren’t sprawling, but “The Backyard,” their inclusive outdoor area, is – with everything from tables to a barbecue and fire pits, all available for guests’ use free of charge.

The Duncan Inn is convenient to a number of no-permit-required beaches in Jamesport, Southold, and Greenport, and also within comfortable distance of the region’s many restaurants (which have prompted some to call it “the Brooklyn of Long Island”…high praise!). If you’re looking for a comfortable place to crash and plan to use your lodging as a jumping-off point for a North Fork adventure, this is an ideal and affordable base camp.


Arbor View House Bed & Breakfast

From three-course gourmet breakfasts to an on-site spa, luxurious Arbor View House is the grande dame of the North Fork. Built around 1780 in the Federal style, then renovated in the Victorian manner of the later 1800s, it’s one of just three homes built or renovated by whaling captains in the area.

A pair of grape vines indicate the area’s prowess in viticulture, but the owners decided long ago to leave the wine-making to other professionals and devote their care and attention to their overnight guests. It shows: contemporary creature comforts like WiFi and flat-screen TVs share space with working fireplaces, lending modern ease to the resort’s Old-World charm. Soak in a whirlpool bath or entertain yourself with picks from the on-site library of DVDs, books, and games; either way, don’t miss the epic breakfasts each morning.