Get Thee to a Winery

Click here to print a full-size map of our winery tour!

Back in 1973, when Louisa and Alex Hargrave purchased 60 acres of former potato fields and planted the first serious wine vines on Long Island, the East End was a very different place than it is today. There were no farm-chic tasting rooms with Hummer limos parked outside, no celebrated chefs creating menus worthy of a two-hour trek. But when a potato pest decimated eastern Long Island’s signature tubers, a Cornell study suggested area farms plant grapes instead, and a beverage destination began to take root.

Decades later, Long Island is wine country, and its East End, just two hours from our own little island, boasts nearly 50 wineries, many producing bottles of fantastic quality. It’s well worth the trip, especially in fall, when a golden glow settles over fields pregnant with pumpkins, and vineyard canopies turn from green to yellow and red; farm stands tumble with lateseason bounty; sweet, thimble-size bay scallops make their annual appearance and local clams and oysters are at their most delicious.

It’s not Napa, but hell, who would want it to be? Here’s our guide to three glorious days in our very own backyard wine country.

Day 1

Most of Long Island’s wineries are on the North Fork, and nearly all have tasting rooms that open around 11 a.m. Kick off your first day at the honey-colored, cedar-shingled barn where 1. Roanoke Vineyards runs its tasting room just west of the town of Riverhead. Owned by Wölffer vineyard manager Rich Pisacano, with wines crafted by Wölffer’s talented Roman Roth, Roanoke’s excellent offerings include the 2007 Marco Tullio, a cabernet franc-merlot blend named for Pisacano’s Chilean father-in-law—he’s 93, but he thinks he’s 20—rich with ripe cherries and spice.

You’ll need stamina to make it through a day of swirling, sniffing and sipping, so fuel up with a proper lunch at 3. The Modern Snack Bar, a gem that’s been satisfying locals since 1950 with big portions of homestyle favorites. Pull a vinyl-backed chair up to a faux-marble Formica table for gravy-topped, utterly tender local duck served with mashed turnips—a perennial favorite that goes great with a glass of Lenz Merlot or Macari Sette from the locally minded wine list.

After lunch, head to 4. Paumanok Vineyards for the gorgeous 2005 Cabernet Sauvignon and the 2009 Chenin Blanc. Winemaker Kareem Massoud’s thoughtful, restrained style has garnered attention from the most exacting urbanites (his 2007 Cabernet Franc is poured by the glass at Minetta Tavern).

Feeling lightheaded? A new sidewalk on Route 25 now connects the neighboring towns of Aquebogue and Jamesport, letting you sip and stroll in safety. The new path starts right outside Paumanok (if you drove, just ask to leave your car in the lot) and lets you walk the third of a mile to 5. Jamesport Vineyards. They donate a portion of the proceeds of their East End series of wines to the Southold Project in Aquaculture Training, an initiative to help save local shellfish.

Amble a quarter-mile east down the road to the gorgeously serene new tasting room of 6. Sherwood House Vineyards in a newly renovated 1880s farmhouse. Gear up your gams for a little more walking with a respite on the cushy shell-gray couch in front of the big brick fireplace, and enjoy the old-world-minded style of winemaker Gilles Martin, who also works at 19. Sparkling Pointe, the all-new, all-bubbly winery on the main road in Peconic. It’s worth the visit for both Martin’s way with fizz and the almost comedically modern (given the old Potato Barn feel of the East End) tasting room with its bubble chandelier and St. Tropez-ish, airy feel.

Take a vino break at 7. Gabrielsen’s Country Farm for a little pumpkin picking, or just to enjoy the acres of unspoiled farmland while the sun sets. With the dinner hour ahead, there are walkable options to consider, too—longtime local favorite 9. Jamesport Country Kitchen, the very first winery-owned eatery; 2. Comtesse Thérèse Bistro which opened over the summer, or the comfortably elegant, sustainably focused 8. Luce & Hawkins which also happens to be one of the prettiest and most luxurious bed and breakfasts on the North Fork—and a great place to call it a day.

Day 2

Start your morning with a house-roasted cup of joe and a plate of house-made pastrami hash and eggs at 11. Love Lane Kitchen. Kill a little time before the tasting rooms open with a stroll down the eponymously named lane to check out the Provençal pottery, French kitchen antiques and rustic signs hand-painted with the name of your favorite North Fork town at 12. La Ferme de la Mer. There’s also the irresistible selection at the 13. Village Cheese Shop, where you can pick up some award-winning East End cheeses for a superb wine-country snack later in the day.

Head north on Love Lane and hang a left onto the Sound Avenue to 10. Macari Vineyards, a family-owned, biodynamic winery producing lovely bottles like the herby 2007 Dos Aguas (named for the nearby Long Island Sound and Great Peconic Bay, it tastes of ripe black cherries and plums) as well as its own line of honey from the farm’s hives.

Lighten your load by checking in to Long Island’s only on-vineyard bed and breakfast at 14. Shinn Estate Vineyards. Owners Barbara Shinn and David Page offer weekend tours of their organically farmed vineyard, followed by a tasting of their estate-grown wines. (Page will also whip up a hearty breakfast for you in the morning—which, seeing as the couple were the talent behind Home restaurant on Cornelia Street, you’d be wise to stick around to eat.)

Just east is the town of Southold, where you can take a late lunch to go at 20. Erik’s, purveyor of outstanding sandwiches, and head to 16. The Tasting Room, a building that was once a speakeasy but since 2003 has been the spot to sample bottles from boutique vineyards that don’t have their own tasting rooms, like Schneider Vineyards and Bouké Wines. Next door in the same building, check out 17. A Taste of the North Fork for some LI-centric delicacies, like Orient Farm lavender honey or North Fork red wine jelly. Head south to 15. Lenz, where Eric Frye’s Bordeaux-style merlots have garnered so much attention.

After a marathon day of tasting-room trekking, you might not think you have room for one more, but it would be a shame to skip the stunning tasting patio at the rosé-only 18. Croteaux Vineyards. Finish with dinner at the newly opened 21. Noah’s, which keeps a healthy selection of local vino to pair with its seafood-minded menu of small plates.

Pedestrian-friendly Greenport—downright hopping for an old whaling town—offers a number of choices for staying the night. (See a full list at the North Fork Bed and Breakfast Association site, nfbba.org.) The minimalist, hipster-friendly Greenporter Hotel is home to La Cuvée Wine Bar and French Bistro, which specializes in farm-to-table offerings; as the weather cools, its famous “winter white bisque” stars rutabaga, turnips and parsnips. At the Stirling House B & B guests wake to the sourdough strivings of the owner; consider VineTime, their all-inclusive package which includes winery tours, vineyard walks and tastings at top area restaurants.

Day 3

After that spectacular breakfast at Shinn, catch the North Ferry for a quick $9 boat ride to Shelter Island. Snag a pulled pork sandwich at 22. Kyle’s, where you should just decide right now to have one of their outstanding jelly donuts for dessert. Then continue south for a dose of fresh air at 23. Mashomack Preserve, a pristine, 2,100-acre, protected natural sanctuary that runs along 10 miles of Shelter Island’s pretty coastline—the suggested $2 donation grants you access to hike through its well-marked trails.

Wave goodbye to Shelter Island as you ride the South Ferry ($11-$12) to Noyak, continuing on Route 114 through the historic whaling town of Sag Harbor, which has maintained its many charms despite all the Hamptons hype. Travel along tree-lined, winding Sagg Road until it breaks open into rows and rows of pretty vineyards, letting you know that you’ve arrived at 24. Wölffer Estates. Probably the grandest of all the tasting rooms on either fork, the broad, butter-yellow, stucco building, with its thick doors, vaulted ceilings, German stained glass and sweeping vineyard views, it’s a great place to try Roman Roth’s fantastic wines, like the barely pink, mostly merlot 2009 Rosé or the heady merlot, cabernet franc, cabernet sauvignon and barbera blend that makes up his 2006 Fatalis Fatum.

About 200 yards from Wölffer sits 25. Loaves and Fishes, the tiny but pricey purveyor of ultra-gourmet takeout, such as rotisserie-style local duck, coriander-and-lime-drizzled crab cakes, and crusty loaves of bread perfect for a wine-country picnic. For a more cost-conscious option, the Pike Farm Stand next door sells raw veggies and goods from 28. Blue Duck Baked Goods, about a 10-mile drive away, and a good stop for outstanding pastry, homemade quiche, sandwiches and pretty cupcakes (the mocha are divine). Or hit Bridgehampton’s favorite brunch spot 27. Pierre’s for BLTs on brioche, Alsatian-style onion and goat cheese tarts, or a two-pound Maine lobster, flambéed with Cognac, dotted with freshly snipped tarragon and snuggled up alongside crispy pommes frites.

Pack up your leftovers and head to 26. Channing Daughters Winery where the incredibly talented winemaker Christopher Tracy experiments with lesser-known varietals like Tocai Friulano, Malvasia, Teroldego and Blaufrankish, and his intensely aromatic white blends, which have won a multitude of converts to Long Island wine and are poured in Manhattan hot spots like Gramercy Tavern, Hearth and Adour. Don’t miss Tracy’s fittingly named Envelope— as in the thing he loves to push—which in the 2007 release was a blend of chardonnay, gewurztraminer and Malvasia Bianca. In the back of the tasting room, you can open a bottle and feast on your locally procured picnic bounty, looking out over the vineyards dotted with owner Walter Channing’s sculptures. It might look nothing like Napa, but it’s just as transcendent a setting for a sip, and much easier a trip from Manhattan.

It Ain’t All Wine

The East End is wine country, but grapes aren’t the only things growing. These farms, farm stands and markets offer great local food to sustain you between drinks.

Garden of Eve
Riverhead
Gothamites love Garden of Eve’s Greenmarket stand, but nothing compares to setting foot on the farm itself. Cooking classes and tours, an impressive on-site store, plus a garlic fest in September.

Wells Homestead Market
460 Main Road, Aquebogue
Abundant local produce, homemade baked goods, fresh mozarella and Long Island duck eggs and duckling.

Harbes Farm & Vineyard
Locations in Mattituck, Jamesport and Riverhead
This small network of North Fork farms and a vineyard includes U-pick fruit, a winery, a market, a café and bakery, even pig races and pony rides.

Wickham’s Fruit Farm
28700 Route 25, Cutchogue
Pick blackberries, peaches, tomatoes, pumpkins and apples in fields that overlook the sparkling Peconic Bay. The cider mill turns out the nectar of the autumn harvest, which pairs perfectly with the farm’s fresh doughnuts.

Sang Lee Farms
25180 County Road 48, Peconic
Gorgeous greens like tatsoi, mizuna and pea shoots; prepared foods from pesto to spring rolls; plus cheese and meats from neighboring farms.

Sylvester Manor
80 N. Ferry Road, Shelter Island
Bennett Konesni is the 15th straight generation to live on 243-acre Sylvester Manor, home to the remains of an 18th-century garden and a wind-powered gristmill. Bennett traveled the world documenting traditional work songs, which he and staff sing while tending the organic veggies.

Sag Harbor Farmers Market
25 Bay Street, Sag Harbor
This Saturday-morning market teems with peerless produce, fresh pasta, local vino, pails of pickles, the morning’s catch from several fishmongers, farmstead cheeses and jars of honey.

Hayground School Farmers Market
151 Mitchells Lane, Bridgehampton
On Friday afternoons from three to six p.m. this school’s front lawn becomes a farmers market. Students sell the veggies they’ve grown themselves, plus local produce, fish and cheese.

Fairview Farm at Mecox
19 Horsemill Lane, Bridgehampton
Get lost in the eight-acre maze of maize; visit the farm animals; hit the mini market for cheese, pies and more; then cross the street to Milk Pail Apple Farm, where you can pick your own apples and pumpkins.

Mecox Bay Dairy
855 Mecox Road, Bridgehampton
Art Ludlow’s cheeses make locals swoon; this stunning farm is home to the 12 Jersey cows whose milk is his muse. Killer on-site farm stand, too.

Getting There

Getting around by car—be it your own or a Zip—certainly allows you to be captain of your own daily destiny. If you drive, make like a wine pro and spit when you’re tasting. Every single tasting room has a spittoon of some sort and if you don’t see one, just ask— they’re happy to provide them.

No car? No problem. Take the Long Island Railroad (mta.info/lirr) or the Jitney (hamptonjitney.com), and give the knowledgeable, affable Jo-Ann Perry, owner of Vintage Tours (631.765.4689; vintagetour1.com) a ring—she’ll pick you up and drop you off at your train or bus stop and take you on a six-hour tour that includes four wineries, a wine lunch and a farm-stand stop all combined with a ton of great information delivered personally. She keeps things small (no more than 13 passengers per tour), so call ahead for reservations.

Another great option for those who want to leave the driving to someone else is Signature Tours (631.599.3317), who also offer pickup and drop-off service from LIRR and Jitney stops. Trips include winery visits, tastings, chats with winemakers, an oyster farming lesson and tasting, plus organic boxed lunches.

Go By Bike!

Map the route on your trusty iPhone, purchase a $5 LIRR bike pass (it’s good for life!) and ride off into the fields. City cyclists will find well-marked bike lanes and wide shoulders all along the South Fork. Just make sure you’ve got a good bike basket to carry home your edible findings.

Reap the Harvest

Presented by Wine Spectator, the weekend of September 24 marks the first annual Harvest wine auction and celebration of eastern Long Island’s fruits of the vine, fields and bays. Bringing together 28 wineries, 22 restaurants and 25 farms from both the North and South Forks, this two-day festival of the senses includes barrel tastings of the ’08 vintages, salons with the area’s most exciting winemakers and chefs, a 10-mile dinner series (with dishes like cold, creamy potato-leek soup with smoked blue fish from Estia’s Little Kitchen and espresso-smoked Long Island duck breast with peaches, microgreens and pickled watermelon radish from A Mano), and the Zachy’s-led wine auction and gala dinner prepared by Keith Luce (of Jedediah Hawkins and the new Luce & Hawkins; and Claudia Fleming and Gerry Haden of lovely North Fork Table and Inn, held on the stunning grounds of Wölffer Estates. Tickets and reservations at harvesteastend.com.