If I have time to drive out, I head to Matador Cigar Shop in Roslyn, NY. It's a little bit of a hike for me, but their humidor is top notch and filled with all of the cigars I'm looking for. Their back area has a pool table and the regulars are always friendly.
If I want to catch dinner or don't feel like straying too far from home, I head over to either Havana Dreams in Woodhaven, NY or The Habana Hut in Bayside, NY.
The former has a decent humidor, an outdoor area for the summer and a bar that serves beer and wine. The latter is the smallest of the three but is the one I visit the most due to its location (right by a bunch of restaurants on Bell Blvd.) and crowd. The humidor isn't large by any means, (maybe 6 ft. wide by 30 ft. long) but it has a good line of tats and padrons and always has something new for me to try.
The regulars are awesome and always easy going and welcoming.