The route from Riverhead to Orient is chock-a-block with restaurants, markets and wineries, and this guide should not stop you from keeping your eyes and mouth open for late-breaking treats. One essential piece of equipment to bring: a cooler filled with freezer packs.
Proceeding west to east, your first stop is North Fork Chocolate Company (740 Main Rd., Aquebogue, 631-779-2963, northforkchocolate.com) for exquisite chocolates and ice cream made with local milk. Next, browse the restaurant-quality kitchen equipment at Bowery Fork (1075 Franklinville Rd., Laurel, 631-298-1818, boweryfork.com) before hitting up The Village Cheese Shop (105 Love Lane, Mattituck, 631-298-8556, thevillagecheeseshop.com) for one of the Island’s best selections of cheese. (Aren't you glad you brought a cooler?)
Head down to New Suffolk for great views of Cutchogue Harbor and casual eats and drinks at Case’s Place (650 First St., New Suffolk, 631-734-8686, casesplace.com) before heading to 8 Hands Farm (4735 Cox Lane, Cutchogue, 631-494-6155, 8handsfarm.com) where you can see sustainably raised sheep, pigs and chickens, buy wool and meat (as well as the remarkable European-inspired charcuterie made by head butcher Julien Shapiro).
Flagging? Stop for an expertly pulled, poured or brewed coffee at North Fork Roasting Co. (55795 Main Rd., Southold, 631-876-5450, noforoastingco.com). Now it’s time to relax with a glass of wine at one of the North Fork’s loveliest and lowest-key wineries, The Old Field Vineyards (59600 Main Rd., Southold, 631-765-0004, theoldfield.com, weekends only during spring).
Finally, watch the sun set over Greenport Harbor from the patio at Little Creek Oyster Farm & Market (37 Front St., Greenport, 631-477-6992, littlecreekoysters.com) where you can shuck your own local oysters and clams and quaff local (as well as excellent nonlocal) brews.