Looks like I'll be there for a weekend. Besides the Madison brewery, are there any shops\breweries worth visiting. And on a side note; any Halloween area activities in Bennington?
Farm Road Brewing is a really cool spot with very nice beers. Bennington Beverage Den has a good selection, though if you're a NYer at this point they will have very, very little that you don't already see here. Four Quarters, maybe some other Burlington stuff that doesn't get NY distro. Prices are cheap as hell though so stock up. There's also Harvest Brewing but the beer is eh and I absolutely hated the vibe so I cannot recommend it.
If you want to drive a little further there is Bear Naked brewing which has a huge deck with a beautiful view which should be great that time of year.
Incredible view, great pizza, but they have no mastered beer making yet. Snow Republic near Mount Snow has some good beers. Worth a stop if you are out and about.