Hotel at a Glance: The Cliffside Resort

The “cliffs” of The Cliffside Resort are actually bluffs overlooking the ocean, on which The Cliffside Resort is built. Thanks to its elevated position, each condo suite at the hotel enjoys a gorgeous view of the Atlantic’s waves. Just over the bluffs themselves, the resort also owns its own private beach, where guests can dip their toes into the water or build castles in the sand.

• Morning coffee with a view: Each suite has a private balcony with a view of the water.
• Perfect your downward dog with yoga classes on the Great Lawn.
• Bring your beach read to the lounge chairs at the quiet, private beach.
• Sip on award-winning wines: Known for its top wineries, the North Fork has a variety of places for you to grab a glass; try the Mattebella Vineyards, just 10 minutes away.
• Eat fresh seafood at the restaurants along Greenport’s Main Street.

Long Island’s North Fork: Award-Winning Wineries, Farm-to-Table Cuisine, and Historic Fishing Villages

At the end of the Long Island Expressway, Long Island splits into two peninsulas—known as the North Fork and the South Fork—that together make up the majority of the famous East End. Considered the island’s agricultural center, the North Fork is dotted with orchards, organic farms, and a growing number of renowned wineries. At Sherwood House Vineyards in Mattituck, you can taste smoky merlots in an antique-filled barn. Paumanok Vineyards, located 15 minutes west, produces estate-bottled Bordeaux-style blends.

A handful of gourmet restaurants in the area make it easy to find food pairings worthy of your favorite Long Island vintage. Just out the back door of Greenport’s The Frisky Oyster is the harbor where its namesake oysters are harvested and delivered daily. Many of the local eateries source their fruits and vegetables from the organic-farm stands along Route 25. Following suit is The North Fork Table & Inn—helmed by a two-time James Beard Foundation Award–nominated chef—which uses organic ingredients in all its menu items, including its decadent desserts.

Despite its growing reputation as a first-class foodie spot, the North Fork is still a low-key farming-and-fishing region. Historic villages line the shores of Long Island Sound, offering opportunities for fishing, crabbing, and clamming. You can rent a kayak and paddle through local bays and estuaries, or head to Orient Beach State Park and hike through maritime forests and bird watch in saltwater marsh.