The Long Island wine country starts, appropriately, where the Long Island Expressway ends. Zip through the sea of big-box stores in Riverhead (stop if you need tube socks) and head north to Briermere Farms (631-722-3931; 4414 Sound Avenue), where you’ll want to buy a blackberry-apple pie, the start of your picnic.
The vineyards are clustered around two main roads, Sound Avenue (Route 48) and the Main Road (Route 25)—most north-south roads connect them. On 25, pull into Bayview Farm Market in Aquebogue, where they’ll roast you a fresh ear of corn. Back in the car, you’ll start to see vineyard signs. Unlike in Napa, there are dozens rather than hundreds, so stop at anything that looks interesting. (Raspberry wine? Well, maybe.) As you approach Mattituck, Love Lane is your destination. The Village Cheese Shop (631-283-6949) has local goat cheese from Catapano’s and plenty of imported offerings as well. Connie’s Bake Shop (631-298-8989) has salads and sandwiches on crusty artisanal breads. La Ferme de la Mer (631-298-4646) will have the perfect Provençal tablecloth to display your growing buffet. (Note to shopaholics: A clothing shop called Mint, just a few doors down, seems to have intercepted a shipment due for Barneys; 631-298-8009). Back on Route 25 in Cutchogue, keep an eye out for Wickham’s Fruit Farm, which not only has the finest local peaches (and homemade doughnuts) but a frigid cheese cellar for respite from the humidity. Then go to the Galluccio Family Wineries (on Route 25, in Cutchogue; 631-734-7089), which has a picnic-perfect dry Riesling and an expansive, vine-side lawn on which to lay your blanket. For more tastings, visit Bedell (in Cutchogue) and Lenz (in Peconic). That ought to put you in the mood for a lazy walk along the Sound in Peconic. Wine country ends in Greenport, where, amid the Jersey-shore-style funk, you’ll want to admire the extravagantly restored carousel. Stop in for a cocktail at Trummer Home (631-477-1880), an outdoor lounge where famed “bar chefs,” brothers Albert and Stephan Trummer, will fix you a honeydew cocktail. When you can fathom eating again, stroll into The Frisky Oyster (631-477-4265) for steak-frites, or Scrimshaw (631-477-8882) on Preston’s Wharf for the postcard setting. After, take the ferry to Shelter Island, where you’ll find rustic accommodations at the Chequit Inn (631-749-0018).
The next day, if you haven’t yet taken an oath of sobriety, board the south ferry to Long Island’s other fork, where the Wölffer Estate in Sagaponack (631-537-5106) is a lovely, Cutchogue-like oasis amid the madness of the Hamptons.