Come Labor Day, there’s one question that every year-rounder must be prepared to field: “What are you going to do all winter?” 

Notice the emphasis on “do,” as if, like the college students, the more imaginative verbs had fled the Island after the third week of August.

The psychology behind this question is complex, but here are at least a few possible motivations. Morbid curiosity (as in, “How much will your off-season plans resemble the plot of ‘The Shining’?”). Escapist fantasy (“Let me guess, surf lessons in Balí, followed by a three-week stage at La Verre Volé in Paris?”). And finally, simple boredom (remedied only by a mental image of me frantically scouring the Island for a proper cappuccino in late February).

Honestly, it’s a fair question. (If I were a summer resident, I’d want to know.) The issue, rather, has always been with my response. You see, I never had any plans — at least not ones that I felt would interest those curious enough to ask. 

That is, until now. Since returning home from Montreal, where I spent the last half a decade, I’ve begun to see the Vineyard winter not as a necessary evil, but rather as an opportunity. And what opportunity isn’t best seized with a glass of wine in hand? 

Which is why, this year, my winter plans will center around a few of my favorite bottles — as affordable as they are delicious — paired with all the local flavors and experiences I’ve so dearly missed during my time away. 

Ryme Aglianico Rosé

Pouring
I like my rosé cold (yes, even in winter), so I suggest keeping this one on ice — or, better yet, on the back porch. 

Pairing
Atria’s Beet with a “T” Carpaccio with Brussels sprouts, goat cheese, and kale. (137 Main St., Edgartown)

Bragging Point
Sonoma-based winemakers Ryan and Megan Glaab are Italian grape specialists, but Aglianico is their calling card. This red grape, native to Basilicata and Campania, is typically associated with full-bodied reds, which makes this rosé a thrilling exception. And thanks to its oomph and complexity, it’s a rosé for the body and the mind.

Hammerling Wind, Sand, and Stars

Pouring
The colder the better. For this sparkling wine, move the bottle from the fridge to the freezer 15 to 20 minutes before you serve.

Pairing
Mo’s Cauliflower Melt with braised greens and cheddar on homemade sourdough. (At the Portuguese American Club, 137 Vineyard Ave., Oak Bluffs)

Bragging Point
Hammerling Wines is a small operation with big dreams. Its founder/winemaker Josh Hammerling is out to prove that California’s coastal ridge is the next great sparkling wine frontier. This bottle, in my humble opinion, might just prove him right.

Florez White Rhino Grenache Blanc 2019

Pouring
Serve it at fridge temperature, but don’t be afraid to leave it on the table once it’s opened to bring out those bright herby aromas. 

Pairing
Grilled swordfish from Net Result (79 Beach Rd., Vineyard Haven)

Bragging Point
UC-Davis alum James Jelks is just as talented as he is groovy. Respected by both natural and conventional wine circles, he is one of the brightest stars in Santa Cruz. This masterstroke of a Grenache Blanc (a Southern Rhône variety) has more body and texture than your typical white, but with a zingy salinity (zalinity?) that leaves you wanting more. 

Maître de Chai Red Table Wine

Pouring
We think all reds deserve a slight chill regardless of the season, so pop this one in the fridge for 15 minutes before serving.

Pairing
Rosewater Market’s buttermilk fried chicken sandwich with pickles, greens, and aioli on toasted ciabatta. (20 South Summer St., Edgartown)

Bragging Point
Maître de Chai’s winemakers, Alex and Marty, both worked as chefs at the French Laundry — which taught them that a dish (or a bottle of wine, for that matter) is only as good as its ingredients. Accordingly, these two spend less time in the cellar and more time rediscovering old, forgotten vineyards in the wilds of Northern California.

Les Lunes Cabernet Sauvignon

Pouring
Bright and lively, this Cabernet is perfect as a winter aperitivo, and best when chilled — so fridge it for 20 to 30 minutes before serving.

Pairing
Grey Barn cheese plate! Lean into their fresher, creamier styles like the magnificent Eidolon. (22 South Rd., Chilmark)

Bragging Point
Unlike most American winemakers, Shaunt Oungoulian and Diego Roig farm their own fruit (currently about 10 acres across Napa and Sonoma). This translates to high sustainability standards and a price-to-quality ratio that is simply out of reach for most small producers.

Keep Wines Pinot Meunier

Pouring
Pop it in the fridge for 20 minutes to bring it just below room temperature before serving.

Pairing
The Larder’s Jambon Fromage sandwich. This fresh, juicy style of red wine is made for lunching in style — especially when delicious cured meats and brie-style cheeses are involved. (342 State Rd., Vineyard Haven)

Bragging Point
Pinot Meunier deserves more recognition. And this wine, sourced from one of Napa’s first certified organic vineyards, provides ample proof. Fun fact: Pinot Meunier might sound a bit esoteric, but it’s actually one of two red grapes used in Champagne production (the other is its celebrity sibling Pinot Noir). Co-owners Johanna Jenson and Jack Roberts also happen to be one of California’s coolest wine-making couples, dividing their time between Napa and Jack’s native Gascony in southern France.

Sam Decker lives in Chilmark and is the general manager of Atria in Edgartown.