FRIDAY
Shelter Island to Greenport to Southold to Riverhead
5:30 P.M. | For my sixth annual cocktail crawl, I’m yearning to explore uncharted territory—a.k.a. the North Fork. After taking the South Ferry from North Haven to Shelter Island, my fellow imbibers and I head toward LA MAISON BLANCHE (11 Stearns Point Rd., 631-749-1633, maisonblanchehotel.com). Dating from 1886, the inn has a sweeping veranda, where we sip BLOODY BULLEITS (Bulleit bourbon, Solerno blood orange liqueur, Antica Formula vermouth, muddled cherries). Outstanding grilled calamari fortifies us for the ride on the North Ferry to Greenport.
6:45 P.M. | At the bar in the Greenport hot spot NOAH’S (136 Front St., 631-477-6720, chefnoahs.com), we sip citrusy SOUR PICASSOS (Absente absinthe, Hendrick’s gin, lime zest, grapefruit juice, tarragon), a fitting complement to ceviche and crab-stuffed deviled eggs.
8:00 P.M. | Hitting our stride, we head to Southold to check out the culinary temple NORTH FORK TABLE & INN (57225 Rte. 25, 631-765-0177, northforktableandinn.com).
Here we sample THE BAUM (Strega, lemon, orange juice, orange soda, saffron bitters), which pairs well with platters of roasted baby beets and asparagus topped with prosciutto and quail eggs.
9:30 P.M. | In Riverhead’s District neighborhood, Dennis McDermott has transformed a 1960s bank building into THE RIVERHEAD PROJECT (300 E. Main St., 631-284-9300, theriverheadproject.com). Mixologist Melanie Hand offers us a DISTRICT SMASH (Corsair gin, basil, strawberries, pepper) and local striped bass ceviche wrapped in butter lettuce.
SATURDAY
Sag Harbor to Bridgehampton to East Hampton
5:30 P.M. | Tonight’s crawl kicks off at Sag Harbor’s MADISON & MAIN (126 Main St., 631-725-6246, madisonmain.com), the new seafood tavern from restaurateur Michael Gluckman and chef-partner Eric Miller. We sip SPICY TEQUILA GIMLETS (Avion tequila, lime and grapefruit juices, rose simple syrup, jalapeño) and feast on Venetian-style soft-shell crabs and local day-boat calamari from Montauk with herbs, sea scallops, and clams.
6:45 P.M. | Off to Bridgehampton and the new organic oasis FRESH (203 Bridgehampton Sag Harbor Tpk., 631-537-4700), most recently the site of South Fork Kitchen. Barman Doug Sheehan serves FRESH GARLIC MARTINIS (American Harvest organic spirit and tomato consommé with clove, coriander, and garlic), while chef Todd Jacobs treats us to vegan summer rolls and tomato and lobster soup.
8:00 P.M. | We motor over to East Hampton celebrity hangout NICK & TONI’S (136 N. Main St., 631-324-3550, nickandtonis.com), which is celebrating its 25th anniversary this year. At the packed bar, we sip MAI TAIS (Diplomatico Blanco rum, Rhum Clément V.S.O.P., orgeat syrup, Pierre Ferrand Dry Curaçao, lime juice, sugarcane) accompanied by grilled calamari salad with spicy chili vinaigrette.
9:30 P.M. | Our final stop of the evening: Jonathan Rapillo’s new venture, SIENNA RESTAURANT & ULTRALOUNGE (44 Three Mile Harbor Rd., 631-604-6060, siennahamptons.com). At the bar, Evan Finkelstein shakes up SOUTH FORK SHIPWRECKS (Pyrat XO Reserve rum, Combier Pêche du Vigne liqueur, fresh lime, demerara syrup, Briermere Farms peach jam) and serves them in a Marie Antoinette coupe. After a nibble of tuna tartare and ceviche spiked with tequila, we say a final toast to another amazing cocktail crawl.