Madison has more of these "towns within the town" than I've seen most anywhere. These are towns that, at one point, were separate and distinct from Madison, but because of Madison's growth, are now wholly (or partially) surrounded by the City of Madison. They also are not subject to the city of Madison's laws and regulations - more specifically, they are not subject to Madison's smoking ban. Confusingly, one of these towns is called "Town of Madison" - a 3.6 square mile bit of land on Madison southside that is the remnants of Madison's pre-capital days. An interesting note: by 2022 the Town of Madison will be completely annexed by the cities of Madison and Fitchburg. The others are Monona, Maple Bluff, and Shorewood Hills.
The village of Maple Bluff, in addition to being the home of the Governor of the State, is also the home of Drakenberg's Cigar Bar. Tucked into a non-descript strip mall next to Manna Cafe at 611 N. Sherman Ave in the Lakeview Shopping Center, it is, as you would guess, a cigar bar - but it also has a pretty decent liquor selection and darn fine beer selection. The breweriana (liquoriana? cigariana?) on the walls is impressive. The lights are low and the air is sweet and hazy from the cigars. Honestly, my favorite thing is the awesome collection of cigar ashtrays.
On tap is a diverse selection of the usual (Guiness, Leinie's, etc.), but also some other more quirky and unique: Flying Dog's Double Dog IPA, Atwater's VooDoo Vator Dopplebock, among others. The bottles are a decent selection of Germans (Franziskaner), Belgians (Gulden Drak) and American (Schlitz).
Drakenberg's is definitely a dude's paradise; but it's not really a date place. So, in comparison to its obvious counterpoint - Maduro - I wouldn't hit it up after taking a date out to a fancy dinner on the square. But, I would go there with my buddies to grab a cigar and beer before going out on the town. It doesn't have Maduro's suave citified pretensions, but rather has the feel of a gentleman's club before that term was co-opted by the strip joints. It's only drawback is that they do allow cigarette smoking inside, so the spicy cigar smoke is cut by the acrid stench of cheap cigarettes.
Like I said, the beer selection is solid and, frankly, unexpected. The taps should rotate frequently and the bottles are interesting and hopefully getting better. It's definitely worth checking out. It won't be everyone's thing, but if you like (or can tolerate) cigars, it's a good place to get something a little different. Unfortunately for us Westsiders, it's not very easy to get to. But you Eastsiders now have Alchemy, Dexters, Malt House, and Drackenberg's to quench your beer thirst.