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Bedell Cellars in Cutchogue, which has a reputation as among the most beautiful wineries around. (Credit: Bedell Cellars courtesy photo/W Studios NYC)

We’ve all gone on that winery trip where we didn’t quite prepare. Maybe we planned our first stop, but didn’t look beyond that. Or perhaps more likely in this time of COVID-19 we had it all sketched out but didn’t make any reservations and found we couldn’t be accommodated at our wineries of choice.

No matter the situation, it’s best to be fully prepared when spending a day among the Long Island vines. Especially when you’re coordinating with friends or planning on using ride-sharing services.

Personally, I like to hit two wineries when headed out for a day of tasting. One stop is great if you’re planning on attending an event or listening to music. Three stops, personally, can be a bit too much in one day when I’m trying to avoid feeling rushed or having too much to drink. Two locations gives you some variety and the time to savor the experience.

I can still remember on my first-ever trip to the wineries stopping off at Castello di Borghese in Cutchogue and then heading east, feeling anxious with only a handful of other options along the way and not much knowledge about any of them (Sparkling Pointe probably should have been my pick). I ended up turning around and becoming even more overwhelmed as I drew closer to home and still hadn’t made up my mind.

I thought about this recently when meeting up with friends on an impromptu day out and finding that with capacity limited by important new social distancing policies, I needed a reservation to avoid waiting at any of the spots we had our eye on.

To help visitors to the region plan ahead, I decided to piece together these winery pairings. No, not wine pairings, but rather location matches based on geography, wine style or theme.

No matter which winery you choose to visit, please check ahead regarding rules, closings and hours as our local wineries navigate the coronavirus pandemic and winter season. Reservations are strongly encouraged!

The Macari tasting room in Mattituck. (Courtesy Photo)

Top-rated: Paumanok and Macari Vineyards

I’ve long maintained that Paumanok Vineyards in Aquebogue makes my favorite local wines. I don’t pretend to be a particularly sophisticated or fussy wine drinker, but I can’t remember ever opening up one of their bottles and it not pleasing myself or the group I was sharing it with. The winery is aided by a stellar reputation and its serious approach to the wine tasting experience – it’s not the place to go to if you want to listen to live music and nosh on snacks. It’s all about the wine. Macari Vineyards in Mattituck and Cutchogue is also a real people pleaser, while also providing an elevated experience. This is a can’t miss pairing if you want to taste only highly regarded Long Island wines.

The Corey Creek Tasting Room. (Credit: Chris Foster)

Best of both worlds: Bedell Cellars and Corey Creek Tap Room

Bedell Cellars is unique in that it has two wineries offering completely different experiences. Its signature Bedell tasting room in Cutchogue is on a picturesque property (or do we now call it Instagrammable spot?) offering tastings of one of the region’s most established and well-respected brands. Corey Creek Tap Room in Peconic, which was updated several years back, is a bit more laid back and features craft beer and other more casual touches. A nice day out is starting your afternoon off at the former and letting your hair down at the latter.

Picking leaves off the vines at Castillo de Borghese. (Credit: Cyndi Zaweski)

OG (Original Grapes!): Castello di Borghese and Lenz

One thing you might not think about when tasting Long Island wine but should is time and history. Vineyards didn’t just pop up when the glaciers melted and formed this island — the earliest vines were planted in the 1970s by pioneers of the local industry. Castello di Borghese sits at the site of Long Island’s first vineyard in Cutchogue. Nearby Lenz, which is on a Peconic property formerly farmed by the local Krupski family, was established in 1978. Both wineries, though not under original ownership, will give you a sense of our start here.

Alie Shaper and Robin Epperson-McCarthy at their shared tasting room, Peconic Cellar Door in Peconic. (Credit: Madison Fender)

Ladies first: Chronicle and One Woman Wines

Not exactly underreported but perhaps something that can’t be celebrated enough is the important role women play in making Long Island wine. Two places that truly celebrate women winemakers are Chronicle Wines at Peconic Cellar Door in Peconic (five small wine brands from two gifted women winemakers under one roof) and One Woman Wines in Southold, which as advertised was built through the hard work of one woman, Claudia Purita. Located in close proximity to each other, they’ll both give you a quality boutique experience.

Outside the tasting room at Lieb Cellars in Cutchogue. (Credit: Courtesy photo)

The Oregon trail: Lieb Cellars and Shinn Estate

Sometimes you just want to get away from it all and spend a day off the beaten path. Lieb Cellars and Shinn Estate are both located on bucolic Oregon Road, with the latter in Mattituck and the former in Cutchogue. Both wineries are also attuned to the details that will make you want to get lost there with good wine and an immersive experience.

Th new-look Sherwood House Vineyards tasting room. (Photo Credit: David Benthal)

Amidst the fall fun: Jamesport Vineyards and Sherwood House Vineyards

And sometimes you just want to be in the thick of it, which this time of year means among the fall harvest crowds that flock to the Aquebogue-Jamesport area for pumpkin and apple picking. These wineries will both enhance that experience. Jamesport Vineyards offers sprawling grounds with pizza made in-house and a range of interesting wines you can really appreciate. Sherwood House Vineyards, which recently underwent a cozy redesign, is also a great place to spend the afternoon, especially as we get later in the season and the wood gets tossed into their fireplace.

The popular Croteaux Vineyards winery serves only rosé. (Credit: David Benthal)

Hip hip rosé: Croteaux Vineyards and McCall Wines

How could I make this list and not include a rosé combo knowing just how popular that particular style of wine is these days? While I believe you can get an acceptable rosé at most places, Croteaux Vineyards in Southold is the all-rosé-all-the-time winery of choice and McCall Wines in Cutchogue pours a perhaps less buzzy but noteworthy pinot noir rosé out of its rustic tasting barn. These places are also a good pairing due to their unique spaces and contrasting styles.

Kontokosta transports you right to the edge of the Long Island Sound in Greenport. (Credit: Eric Striffler)

Eastbound and down: Sparkling Pointe and Kontokosta

Sometimes pairing a winery is as much about geography as anything else, so if you’re looking to catch a ferry out of Orient or Greenport or staying at a hotel on the eastern edge of the North Fork, Sparkling Pointe Vineyards in Southold and Kontokosta Vineyards in Greenport make for a good two-stop afternoon. As the name suggests, Sparkling Pointe is focused on bubbly and Kontokosta is the only winery located directly on the Long Island Sound. Both provide great ambiance.

A toast to Palmer Vineyards in Riverhead. (Credit: Krysten Massa)

Go west: Palmer and Baiting Hollow Vineyard

Most of you will be going west and for young men and women Palmer Vineyards in Riverhead and Baiting Hollow Vineyard in Baiting Hollow are often wineries of choice. Both usually have good lineups of live music in summer and fall and as the two eastern most public wineries (the great Roanoke tasting room in Riverhead is private), they’ll have you instantly closer to home. I would recommend starting at Palmer and spending a little more time there.