Spend a day exploring some newer additions to the area’s slate of 48 wineries. Start out with a tasting ($17 for four wines) at Sparkling Pointe Winery and order caviar ($14 to $26) or Vosges chocolate ($10) from a vineside armchair. Head to Shinn Vineyards for the new vintner tasting ($25), during which owner David Page lets guests sample from the barrel and taste current vintages of reserve wines not available during regular tastings. Call ahead to One Woman Wines in Southold to see if they’re hosting Tastings Under the Stars, a bi-monthly campfire outing from 6 to 10 p.m. with cheeses, tapenades, hummus, and other tapas available ($6 to $10).
Catch the sunset at one of the best spots on the North Fork. Drive about four miles up Nassau Point Road in Cutchouge to a thin neck that juts out into Peconic Bay. Once you can’t drive any farther, you can walk out on the sandy peninsula, which puts you halfway across the bay. (Depending on where the tide is, visitors may be able to walk into knee-deep water.) Stake out a spot and bring a bottle of wine as you watch the night sky unfold while you’re surrounded by water on three sides.
Sip pink wines and pick up cooking tips at Croteaux Vineyards, where they only make rosé. Tastings ($10 to $15) take place in a gravel-lined garden styled to look like Provence with cheerful red-metal seating. Chat up owner Paula Croteau about her first cookbook, Farmhouse Kitchen Favorites, which was published in November and focuses on seasonal recipes. In the winter, she teaches cooking classes in the winery’s farmhouse.