1. Where to Stay
There are no bad views from the Shinn Estate Farmhouse (from $275), the only on-vineyard inn on the North Fork. Enjoy a bottle of Shinn’s rosé in the Northfield Room, with its sunset view of the Long Island Sound. Hard-core oenophiles should sign up for a Wine Asylum Weekend ($1,000 per couple): three days of working in the vineyards, tasting wines, and refueling with meals cooked by co-owner David Page, who also owns New York’s Home with wife Barbara Shinn.
The year-old North Fork Table & Inn ($250), houses four elegant rooms in a white-columned Colonial on Route 25 in Southold. Meals are served in a pretty, pale-blue dining room, where a nightly changing menu features dishes like crispy-skinned black sea bass in a carrot-ginger broth, and, of course, a good local wine list.
At the Red Barn Bed & Breakfast (from $175) in Jamesport, owners and Slow Food members Linda and Jim Slezak serve lemonade with homemade cookies on the wraparound front porch and a three-course breakfast using mostly local, organic ingredients. Take public transportation out to the East End, and they’ll pick you up at the station—and knock 10 percent off your room.
Jamesport resident Jeff Hallock recently completed a four-year restoration on the once dilapidated, now immaculate former sea captain’s home, the Jedediah Hawkins House (from $325). The Key-lime-colored mansion, originally built in 1863, has six creatively decorated rooms, but the top-floor Belvedere Suite is the best, with its 360-degree views, and telescope for stargazing.
2. Where to Eat
Start your day off at Delicious (24375 Main Rd., Orient; 631-477-3223), an aptly named restaurant that shares digs with the Orient Gas Service Center (whose sign you’ll more easily spot from Route 114). The crazy-strong Danesi coffee is imported from Rome, and the house-made apple strudel, bread pudding, and to-go cups of thick chocolate mousse are worth the ten-minute drive (or twenty-minute bicycle ride) from Greenport.
Pretty, white-tiled Love Lane Kitchen (240 Love Ln.; 631-298-8989) on Mattituck’s storybook-quaint main street also does a mean breakfast, with homemade rolled-oat granola. For lunch, pick from a stack of under-$10 sandwiches with ingredients like prosciutto di Parma, grilled hangar steak, and local goat cheese.
The open kitchen in Greenport’s the Fifth Season churns out an aromatic bounty of local products, like duck from Aquebogue’s Crescent Farm and organic veggies from Satur Farms in Cutchogue. The beers all hail from New York, and the wine list is exclusively local.
A few storefronts away on Front Street is the deliciously quirky Frisky Oyster, made chic with bright-red flowering-vine walls and a cultural-immersion menu that sails through the Mediterranean, Asia, and back. Parents should call ahead for a sitter—kids under 6 are not allowed.
3. What to Do
The North Fork is not only obsessed with organic veggies and homegrown wine. It’s also a dairy hot spot. Head toward the town of Peconic on Route 48 and look for signs for Catapano Dairy Farm, where you can taste some award-winning chèvre and a chocolaty goat-cheese fudge, and then visit with the farm’s 90 hard-working goats. Next, hang a left onto Love Lane for lunch at one of the tile-topped tables at the Village Cheese Shop (105 Love Ln.; 631-298-8556), where you can feast on regionally based cheese plates.
Strict permit-only parking rules on the East End make it tough to get to the beach. Get around it by stopping into Cliff’s Elbow East (50 North Sea Dr.; 631-765-1203) off Route 48 in Southold, where local oysters and clams on the half-shell are accompanied by a great list of Long Island wines. Park in the restaurant’s lot, and then stroll over to long, quiet Kenney’s Beach, one block north. Compared to South Fork beaches, it’s never overcrowded and often dotted with families camped out for a low-key day of sand and sun.
4. Insider’s Tip
Since there’s no way you can visit all the local wineries, put together a crib sheet of must-taste bottles at Greenport’s VINe, which offers a dozen-odd Long Island wines by the glass. Drop in on Fridays, and take part in the weekly winemaker series, with complimentary tastings and snacks. The former speakeasy the Tasting Room in Peconic also has tastings and flights of small-production Long Island wines, several of which you can only find here.
5. An Oddball Day
There are few sights as stunning as a clear night sky in Eastern Long Island, and on Saturdays from dusk until midnight, the Custer Institute observatory—which got a brand-new galvanized-steel dome in 2006—opens its high-powered Meade telescope to the general public for free. Beforehand, though, pop over to North Fork Potato Chips all the way at the end of the Cutchogue Business Center (read big, gray warehouse). During regular business hours, owner Carol Sidor will sell you a case of 24 bags for $18—a sharable, and addictive, stargazing snack.
6. Related Links
The farm-to-table journal Edible East End lists wine and food events on both the North and South Forks.
For a full-service listing of lodging, real estate, restaurants, and anything else you’d like to know about the North Fork, check North Fork Magazine.
The Long Island Wine Council provides printable maps of all the local vineyards.