Just across the bay from the overhyped Hamptons lies the North Fork—a cluster of towns set among bold new vineyards and peppered with buzzworthy restaurants. The latest of the area's wineries, Shinn Estate Vineyards (2000 Oregon Rd., Mattituck; 631/804-0367; www.shinnestatevineyards.com), is owned and run by New York City restaurateurs David Page and Barbara Shinn. Drop in for a tour of their 22-acre estate and a taste of their fruit-forward Merlot and bone-dry rosé. • North Fork Food (43715 Rte. 48, Southold; 631/765-6264), a sunny gourmet shop and café, is a perfect lunchtime stop for a bite on the shaded patio (try the seared tuna or meat loaf), or for a picnic packed to go. • You can also refuel at Delicious (24375 Rte. 25/Main Rd., Orient; 631/477-3223), a café that serves rich espresso and fresh croissants and is attached to, of all things, a gas station. • Some of the area's best restaurants are on Greenport's quaint Front Street, including the Fifth Season (No. 45; 631/477-8500; dinner for two $90). The bistro, warm with saffron-colored walls and exposed brick, pairs island produce (in dishes such as roast duck with cherry and fig chutney) with local wines. • Down the street, the Frisky Oyster (No. 27; 631/477-4265; dinner for two $100) is a must for dirty martinis and flawless steak frites in a sexy, low-lit room. After dinner, call it a night at the Greenporter Hotel (No. 326; 631/477-0066; www.thegreenporter.com; doubles from $299). The refurbished 1950's-era motor inn just added a 5,000-square-foot spa with—what else?—wine-inspired treatments.
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