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Here are a few general guidelines to start with:
1. Sweet beverages in general pair well with saltier, more aggressive cheeses.
2. Subtle ones require more balanced and nuanced ones from the cheese.
3. Bubbles will complement dense, rich creamy cheeses, and go particularly well with those made from goat's milk.
When you're entertaining, you may want to rein in your preferences for the wildest, most exotic flavors in order to please large numbers of people. But that doesn't mean being boring.
The Best Cheeses for Winter Beers
This time of year, the shelves of your favorite beer retailer are full of special winter brews from many fine breweries. There really is no consensus among brewmasters on exactly what a holiday beer is: some are cinnamon-spiced and redolent of ginger and clove, while others are piney and roasty.
Most of these brews lean toward the malty, slightly sweet side, which makes them an ideal match for some of the firm sheep cheeses that can be found this time of year. Try the standard bearers: Vermont Shepherd, Dante, and Weston Wheel. A newer option, Singing Brook from Blackberry Farm in Tennessee, is well worth the pursuit. These cheeses offer a well articulated flavor; they start buttery, have herbal components in the middle, and finish with a distinct and pleasant edge of salt. The slightly sweet element in the beer will balance out the salt nicely.
Dark seasonal brews like Smuttynose Winter Ale and seasonally-appropriate stouts pair well with alpine cheeses like Pleasant Ridge Reserve and Springbrook Tarentaise. These cheeses are dense and often redolent of roasted nuts; that aspect of their flavor matches the nuttiness of roasted malt (which is what makes darker beers dark) and creates a harmonious pairing.
The Best Cheeses for Wintry Wines
Many of us switch to red when the weather gets cold, and unfortunately, red wines are much harder to pair with cheese than their white or pink counterparts. In fact, many experts have thrown up their hands in exasperation and announced that cheeses shouldn't be paired with red wine. I roll my eyes at that kind of defeatism, but cheeses must be chosen carefully and with an eye toward versatility. Alpine cheeses like Pleasant Ridge Reserve or firm sheep cheeses like Vermont Shepherd are pretty safe choices for pairing with many red wines. If you're serving Bordeaux or Rhone Valley reds, try a good quality cheddar like Cabot Clothbound, Montgomery's Cheddar, or Keen's.
The Best Cheeses for Champagne
The best approach for bubbly is to serve goat's milk cheeses (which echo the wine's minerality) and very creamy cheeses (which benefit from the cleansing, palate-refreshing bubbles.) Kunik from Nettle Meadow Farm in upstate New York is an ultra rich, creamy cheese made mostly from goat's milk. It's dynamite with Champagne. You could also consider serving a variety of options from California's Cowgirl Creamery. Their Mt. Tam, Pierce Point, Devil's Gulch, and Inverness cheeses all pair so well with champagne that you'll want to make sparkling wine a year-round drink.
What About Egg Nog?
I'm fond of boasting that there isn't any beverage that I wouldn't pair cheese with, but egg nog is the exception to that rule. It's so heavy with dairy already that any more would be overkill.
Maybe you should serve gingerbread cookies instead?