Unfortunately there aren't many good beer bars on the island--actually, there isn't one at all. Whale's Tale can be found everywhere though. Try and hit Brotherhood of Thieves.
Welcome to The Brotherhood of Thieves- Nantucket 1840’s whaling bar and restaurant
It's a pretty cool pub with low ceilings and dark wood right in the center of town. If you're looking for a liquor store, hit Hatch's as they've got the best selection on the isalnd. It's located at 129 Orange Street, which is a short ride from Main Street (you could walk it also--probably 15 minutes).
An excellent place for brunch and dinner is Black Eyed Susan's. I'm not sure if they'll still be open in October as they're seasonal, but it's a must hit. BYOB and cash only.
http://www.black-eyedsusans.com/
Definitely go to Cisco when you're there. Have the sampler and sit out on the patio. My personal favorites are Indie Pale Ale, stout, porter, and bailey's. They've tweaked the Whale's Tale recipe in recent years for the worst in my opinion--it used to have such a nice floral aroma with a good biscuity malt backbone.
Enjoy the island!
Nantucket
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