Hit Siro's after the races, and then downtown. Go up and down Broadway, take a look at some of the hotspots -- you'll see 'em, LOL. Off Broadway, yes, The Parting Glass is a stop, City Tavern, Mare, 9 Maple, Gaffney's, and more. For dinner -- some of my favorites are Lanci's, Chez Sophie, Doc's Steakhouse, Grey Gelding, Springwater Bistro, and One Caroline.
Now, if you are looking to enjoy a cigar -- the only place you can smoke inside is the smoking lounge at The Wine Bar, or outside area at 9 Maple and Mare (I think you can still smoke outside at Mare -- not sure, so check first).
Enjoy!
Eric
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