We knew something had changed on the North Fork of Long Island. There on the Sunrise Express bus (always the smartest way to travel the two and a half hours from Manhattan) was proof: a Goyard duffel bag instead of the usual floral tapestry roller. The area once known for its farmland and vineyards, stitched together by a string of little towns—Greenport, Mattituck, Cutchogue, and Southold—has at last made way for some serious style.
Credit Dennis McDermott and Hank Tomashevski, whose Greenport restaurant, the Frisky Oyster, became the first real pocket of sophistication when it opened three years ago. Across the street from the Whiskey Wind Tavern and the Arcade variety store, the place is casual enough for its village locale (despite the red flower-print wallpaper supposedly inspired by curtains in Richard Gere's house) but still serious enough to mark a real departure. McDermott and Tomashevski, who also cater high-profile events and private dinners in New York City, even made history when they landed Greenport a few mentions in "Page Six" of the New York Post. Beyond the buzz, what sets the Frisky Oyster apart is the food: The salad of frisée, lardoons, and Gorgonzola; the fantastic steak frites; and the chocolate pot de crème are regulars on the menu, which changes daily along with the wine list (pray they have the tamales and Pascual Toso Malbec on your visit). The restaurant has opened the door for other promising newcomers as well. There's Scrimshaw, right on Preston's Wharf, and the cozy Fifth Season, where chef Erik Orlowski, a Pino Luongo alum, creates what he calls farm-to-table cuisine. We could have done without the Fifth Season waiter's treatise on the Slow Food movement, but we loved how the ingredients of the Granny Smith apple-Gorgonzola tartlet suggested two of our stops the next day: Catapano Dairy Farm in Mattituck and Wickham's Fruit Farm in neighboring Cutchogue.
Roadside stands, mainly along Route 25, are central to the North Fork experience. The pickings range from blackberry and rhubarb pies at Briermere Farms to eggplant and corn on the cob at Sep's to Asian vegetables at Sang Lee (pick up some homemade pesto). The bounty that earns the most attention, however, is the wine. First stop on the tasting trail should be Bedell Cellars, the 25-year-old vineyard started by movie producer Kip Bedell—it's all white clapboard, French-paned windows, and oversize club chairs. The second, Lenz Winery, another maker scoring high marks for its old-vines Merlot, feels more like a barn, but the staff here is knowledgeable and always happy to show you the spots where you can spread out with your own food and a bottle or two of their wine.
There is also, finally, a place to rest your weary self. Greenport's year-old Harborfront Inn is beautifully done. Even if it lacks the B&B charm you might crave in a country hamlet, the breakfast of cheese scones and blueberry muffins from the Peconic Baking Company fills the void. Heartier fare—and a more lived-in vibe—is just up the block at Bruce's Café (order brown-sugar bacon with your omelet). Just as you start thinking the North Fork has gone completely city, you'll step in and see a folksy hooked rug of an off-kilter mermaid. Her name, naturally, is Triumph.
HARBORFRONT INN Rates, $260-$650. 209 Front St., Greenport; 631-477-0707; www.theharborfrontinn.com
BRUCE'S CAFE 208 Main St., Greenport; 631-477-0023
THE FIFTH SEASON Dinner, $90. 45 Front St., Greenport; 631-477-8500
THE FRISKY OYSTER Dinner, $100. 27 Front St., Greenport; 631-477-4265; www.thefriskyoyster.com
SCRIMSHAW RESTAURANT Dinner, $100. 102 Main St., Greenport; 631-477-8882
BRIERMERE FARMS 4414 Sound Ave., Riverhead; 631-722-3931; www.briermere.com
CATAPANO DAIRY FARM 3985 Sound Ave., Mattituck; 631-298-0043; www.catapanodairyfarm.com
SANG LEE FARMS 25180 County Rd. 48, Peconic; 631-734-7001; www.sangleefarms.com
SEP'S FARMS $ Rte. 25, East Marion; 631-477-1583
WICKHAM'S FRUIT FARM Rte. 25, Cutchogue; 631-734-6441; www.wickhamsfruitfarm.com
BEDELL CELLARS 36225 Rte. 25, Cutchogue; 631-734-7537; www.bedellcellars.com
LENZ WINERY Rte. 25, Peconic; 800-974-9899; www.lenzwine.com
$ Establishment accepts no charge/credit cards or accepts cards other than the American Express Card.