The type of artisanal cheddar I was writing about yesterday - mature, full-flavoured, unpasteurised - isn’t the easiest cheese to match with wine.
One’s instinct is to drink red but it’s a struggle. You don’t want anything too light and graceful or, conversely, too full-bodied and tannic. There can be some wild flavours in a cheese like this which I think are best matched by an equally artisanal wine - and old Syrah/Shiraz, Grenache or Mourvèdre, maybe - or a blend of all three. Or a good Zinfandel. But don’t introduce blues or smelly washed-rind cheeses to the cheeseboard as well.
Vintage port is surprisingly - or not so surprisingly - good as we confirmed at a cheese and wine tasting I conducted for Decanter last year. One associates it more with stilton but it’s equally good with a fine cheddar. But it’s not the type of wine to open with a ploughman’s or other light lunch.
That distinction goes to a traditional British ale which I’m not sure isn’t the best pairing for this kind of cheese, especially if you serve it with an onion pickle or a chutney. Something like Adnams Broadside or Young’s Special. If you find British beers too bitter a sweeter-flavoured American IPA may be more to your taste, being a classic example.
If you’re looking for a terroir-based match a farmhouse cider would be the obvious choice for an authentic Somerset cheddar, especially if you serve it with apples or an apple chutney. Personally I prefer a medium-dry style but that’s up to you.
Apple-based aperitifs or digestifs such as Pommeau and Pomona which is made by the Somerset Cider Brandy Company can also work very well. Obviously they’re more alcoholic than cider but you could serve them instead of port for after dinner drinking.
Other possibilities, less mainstream: a full-bodied oaked Chardonnay pairs surprisingly well with cheddar as does a good rich whisky like The Macallan or Famous Grouse. Sherry can also work well particularly if you serve your cheddar with nuts - I’d choose something like a palo cortado. Other possibilities would be a medium-dry Madeira or a 10 - or 20 - year old tawny port.