It's hard to beat a good maduro paired with a good Stout or Porter. In the winter time I like to pair maduros with heavy Stouts/Imperial Stouts like Brooklyn Black Chocolate Stout, Old Rasputin Russian Imperial Stout, Buried Hatchet Stout, Samuel Smith's Oatmeal Stout and Samuel Smith's Imperial Stout (just to name a few). As far as Porters go, Samuel Smith's Famous Taddy Porter and Sierra Nevada Porter really hit the spot. The Stone Smoked Porter also pairs really well with maduros (IMHO, at least).
Damn, this thread is making me miss the winter already.