Shelter Island was once the anti-Hampton – quiet, windswept, and casual. Lately, alas, it has been bitten by the chicness bug and in summer months can get downright crowded. But winters are still glorious. Especially at the classic, rambling Ram’s Head Inn, built in 1929. Ferries to Shelter Island run all year round, and the inn is open for the last three weekends in February. The tennis courts may be closed, but the desolate beauty of the island and the inn’s gracious service, cozy rooms, and elegant food are all you’ll need. On the way home, take the ferry to Greenport. The route along the North Fork is more picturesque than the South Fork’s, and the wineries along the way are open to walk-in visitors year-round. (Hargrave Vineyard is a good bet, as is nearby Lenz Winery.) After all, there’s no better way to wind up a winter weekend than sipping Cabernet at dusk.
Details Ram’s Head Inn, 516-749-0811 (rooms start at $95 during the off-season); Hargrave Vineyard, 516-734-5111; Lenz Winery, 800-974-9899.