When we step off the train in Southold, Long Island, I can’t help but think, “We’re not in New York City anymore.” Just two and a half hours from Manhattan, the green, wide open spaces of the North Fork of Long Island seem as far from the congested city as can be. The most striking difference is the presence of land, lots of land. That most coveted of commodities in Manhattan is present here—in all its sprawling, lush glory: along its sidewalk-less road, between, behind, and in front of its single family homes and, most importantly, in and among its vineyards.
The Long Island Wine Country celebrates 40 years this year. In wine speak, where “vintage” and “aging” are the highest ranked of buzz words, 40 years doesn’t bear a lot of weight. Napa Valley and even Oregon wine countries date back to the 19th Century, and don’t even try to compete with Tuscany or Bordeaux. But amid these young vineyards one has the opportunity to witness some great history, including Southold, the oldest English settlement in New York. Plus, what it lacks in years, Long Island’s Wine Country makes up for in heart. And beauty. And some darn good wine. And at less than a three hour train ride from Manhattan, the sprawling, verdant setting makes a welcome break—and easy day trip—from the busy, overcrowded city.
Where to Wine Away the Hours
The idyllic courtyard of Croteaux Vineyards could only be closer to a fairytale if they served pink wines. Oh wait, they do. I’m not a sweet wine fan, so I had my doubts about an all-rosé winery, but Croteaux managed to convert me. Instead of using the by-products of red wines as is typically done in the making of rosé, at Croteaux the fruit is harvested early and for the explicit purpose of making the pink wines. The result is not only a pretty color but a crisp, refreshing wine that can hold its own against the usual whites or reds any day.
There is a small open-air lounge with cushions and benches, but a shaded table in the courtyard is the place to be. If you’re lucky you’ll get a visit from Sargent, the friendly, honey-colored terrier who belongs to the Croteauxs. The family moved to the area in 1992, and only fell into the business of winemaking when they purchased the neighboring farm to preserve its history. They live in the Victorian-era farmhouse at the back of the property, and are working to make the Dutch Colonial barn—which was built in 1749 and borders the courtyard—into a tasting room. For now though, wine lovers are content to gaze at the historic structure. With its enchanting setting and enriching history (as told, if you wish, by the proprietor himself), Croteaux takes the tasting experience to a whole new level.
Plan to arrive when it’s time for lunch in order to maximize the experience with a fruit, cheese and baguette basket ($10). Tasting here is inexpensive to boot: $7 allows tastes of three wines, plus the pink cuvee and a spiced sangria. And odds are good you’ll want a bottle for the table ($18) to help savor the experience.
After the intimate Croteaux experience, the spacious, more traditional Corey Creek Tasting Room was a jarring difference, but the friendly mother/daughter team manning the counter made us feel instantly welcome as they enthusiastically explained the tasting options: $5 (three wines), $8 or $12 (four wines). The wines served here come from Bedell Cellars, one of the larger Long Island wineries, and received mixed reactions from the group of tasters. The standout here of the four was, not surprisingly, the chardonnay; this is what Corey Creek is best known for, but it should be noted that the nice, robust Cabernet Franc lingered pleasantly on our lips a while after.
We spaced out our tastings by commandeering a table on the breezy deck, where we then paired each wine with the vineyard’s savory views. Many tables had chosen to share bottles out on the deck, which is also a way to enjoy the singer/guitarist perched in the corner.
As small as Croteaux is, Osprey’s Dominion Vineyard is large. And yet here it’s easy to feel like just one of the gang. The tasting room is comfortable and spacious, but when the weather is nice, the place to be is out on the vast lawn, which stretches out to the vineyard with plenty of space to frolic in between. Picnic tables are scattered along the edge of the lawn, which is reminiscent of a Technicolor Gatsby party, sans the 1920s garb. Here you’re sure to become fast friends with folks at the scattered picnic tables, and even faster friends with the group crowded around the “wine bar,” which sells wine both by the tasting and the bottle. If you’re opting for the $5 list rather than the limited releases, you’ll be sampling five different wines, ranging from whites, rose, reds, and dessert wines. (Hold on to the citrusy yet subtly sweet flavors of summer a little longer with a bottle of 2007 Semi-Dry Riesling for $14.)
The best part, though, is the lawn party itself. On the weekends a band inhabits the small stage set up midway between wine bar and vineyard, with plenty of space to dance in between. If you weren’t friends with the picnic table cronies before the music started, you’re sure to be when the band starts up.
A votre santé!
Bottle this list:
Croteaux Vineyards | 1450 South Harbor Road, Southold, NY | 631.765.6099 | Croteaux.com
Corey Creek Tasting Room | 45470 Main Road, Southold, NY | 631.765.4168 | Coreycreek.com
Osprey’s Dominion Vineyard | 44075 Route 25, Peconic, NY | 631.765.6188 | ospreysdominion.com
How to get there: Ready for your own day of wine and rosés in North Fork? Well, get thee on a Long Island Railrood train to Southold, and do it quickly. Weekend trains depart Penn station at 9:16 am ($16.75 each way) and take just under three hours, placing your right on track to hit that lunch at Croteaux target. The Southold train station is approximately one mile and a half from Croteaux, and from there the wineries are clustered together on the main road. Make sure to purchase a $5 permit at Grand Central to bring your bike on board (good forever).
To get from place to place, you have a few options. There is, of course, the old standby of hiring a tour or limo service to do all the dirty work for you. These average around $100 per person. That said, we don’t recommend the standard tour routes. For one thing, you can personalize your wining experience far more by going on your own, and, more importantly, many wineries (especially the smaller and more interesting ones) do not accept tours.
A far better route would be to bring your bike and ride between wineries—it’s an easy trip and a whole lot of fun. (Of course we urge you not to drink and bike too heartily.) Walking from Southold is also doable, but there is no sidewalk, so take care walking on the shoulder of the road.
If you still feel you must drive, check out our mini-guide to hybrid rentals.
For more ideas on places to sip and sleep in the North Fork, read Vine Time.
View Long Island Vineyards in North Fork by Bike in a larger map
Sarah Knapp is a Brooklyn based entrepreneur whose love for the outdoors and community building led her to the October 2013 creation of OutdoorFest. She has a BA in History, is a Wilderness First Responder and a NY state hiking, camp and boating guide. Her proudest achievement to date is reading the Aeneid in Latin. 
Allison was one of our first top writers and Chief Editor but is no longer working with offMetro. Allison is a native New Yorker, who has lived in Rome, Tuscany, Melbourne, Toronto and Los Angeles. She frequently contributed travel pieces to Family Travel Forum, using her own children as guinea pigs as they travel the globe. She never missed a chance to sample local delicacies, as her love for travel goes hand-in-hand with her love for food and wine. 
Josh Laskin is a freelance travel writer and photographer based in the White Mountains of New Hampshire. When he is not at work or on the road, you can find him in the mountains snowboarding, climbing, hiking, fly fishing, mountain biking, and eating bagel bites.
Annie is a travel writer, environmentalist, and surfer based in Venice, CA. She heads up our West Coast team, keeps our grammatical errors in check, and makes sure our California writers always have a plan for their next adventure. Follow Annie’s travels @annelisemcb.
Carly Pifer is a freelance writer who has been known to follow whims inspired by romantic movie scenes or colorful street style shots to India, Japan, Tunisia and Argentina. After stints living in Seoul, Boston, Paris and Los Angeles, writing and searching for something intangible, she landed somewhat steadily in Brooklyn and has begun to find inspiration in her more immediate surroundings. 
Kate E. O’Hara is a New York based freelance writer and photographer who loves all things food—especially the people who make it and market it. Her writing aims to capture the essence of the food experience; the stories that go well beyond a plate of ingredients. In addition to her love of food, Kate is also known to have a hankering for red wine and craft beer. You can also find Kate on Instagram