Thompson St, SoHo

For a street that sprawls two very high density neighborhoods, there isn't much going on by the way of Thompson Street. It starts at Washington Sq Park, which is nice, but a lot of streets do. Right at Thomps and Wash Sq South there are two churches across the street from one another. This kind of amuses me because one of them is a Catholic Church and the other one is notoriously liberal (i.e. helps people with drug problems, abortion issues, provided sanctuary for rioters).
There are a couple of chess shops on this street which I find kind of weird. Of all the little streets surrounding Wash Sq Park, it's interesting that two Chess shops are on the same one.
There's a bar called The Dove on Thompson at Bleecker that I love. It's a really cozy bar that always has a great vibe. It was an Italian Place for nearly 100 years before that. It's the place where Cher gets proposed to in Moonstruck. John Patrick Shanley was a frequent customer. And, apparently, Dylan Thomas had his first meal there. Obviously, it's not the same place; but, it's still such a cool place.
Once you get south of Houston, this is a pretty Italian street. It has a ton of mobster blood all over the sidewalks and roofs (people were often strangled and dropped in this area. Some really famous Mob coups happened on Thompson. There are a few little stores and a ton of apartments. But, other than that, it's relatively quiet . . . . for downtown New York.

You've heard of the Washington Square Park chess scene, right? The southwest corner tables are usually populated by chess hustlers, who do a lot of shouting and thinking out loud to distract you, plus their gullible victims who think they're too too clever, plus the amused onlookers and random Washington Park crazies. If you'd like to get hustled on the main playing field, and maybe take down one of these cheap chess-masters yourself, you can first get in some practice at Chess Forum or The Village Chess Shop, both on Thompson Street. Both establishments have a gorgeous selection of chess boards on display in the windows and also for sale, as well as books and other chess paraphenelia. There are always people loitering around these places to play a couple of matches with, so you might end up getting informal lessons. Two other important spots on this street: Generation Records for the avid music fan, and the Smoke Shop, where you can get exotic cigarettes from all over the world, and a nice assortment of rather tacky, ornate hookahs. I also love Stella Vintage for one-of-a-kind dresses and such. Thompson Street hasn't quite survived the NYU student invasion, but some of the important landmarks remain.