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Confession: I never feel quite cool enough to fit in at Longman & Eagle, where the young and beautiful staff all seem to wear oversized hipster glasses and have a slightly detached air. Whiskey, of course, helps alleviate that out-of-place sense, and Longman & Eagle offers nearly 150 different types, a fifth of which are available for just $3 a shot. This bar is notoriously crowded in winter, when the disaffected artsy crowd is waiting to get seated at the gastropub. During warm months, a patio opens up, giving you more breathing room. If you want to make a night of it, reserve one of the rooms upstairs at the Longman & Eagle Inn, which will also score you a rare reservation at the popular farm-to-table restaurant. Only hotel guests are granted such a thing.