I work in midtown Manhattan. I can remember not all that long ago (10 years? 12? This was during the last gasps of the cigar boom) I could stroll out of the office at lunchtime and make my way to Barclay Rex, Arnold's, Nat Sherman, Davidoff, Connoisseur, and De La Concha. Each place had many beautiful pipes on display and a tobacco selection somewhere between decent-to-great. J&R Cigar was also nearby and had large cases of pipe tobacco downstairs (Dunhill, Rattray, McClelland and more). Even the head shops would sometimes have an overpriced Don Carlos in the display next to the hookah.
Davidoff bought out De La Concha and the pipe activity there is greatly reduced. Inventory is not even a quarter of what they used to have. Besides the house brand pipes it looks like they are just selling through what came with the purchase. Nat Sherman has one little case – maybe 20 pipes total. All the other stores have closed.
My point is that even near the "crossroads of the world" there are only two and the pickings are scant. Internet commerce has killed the rest.
I was in the Owl Shop maybe 10 years ago and I remember thinking then that their selection was awfully thin. Maybe things have changed since but not to look at their website. The word 'pipe' doesn't appear once.
We live (for now) in the golden age of shopping online. I think your best bet is to deal with reputable, out-of-state vendors. Order a few pipes, examine them at home at your convenience, and ship back the ones you don't care to keep. Grab a couple of cheap cobs while you're at it to round out your rotation.
Good luck!