Mac Dougal St, Greenwich Village

Macdougal used to be a very artsy street. And, a lot of that vibe is maintained but not quite to the degree that I wish it were. I know NYU is to blame for a lot of that. But, it's unfortunate that the area that was designated for the arts set is now much to expensive for any of the artists to actually live in.
The block between 8th and Waverly was really happening during the beat generation. The north corner of Macdougal and 8th was a popular bookstore where Bob Dylan and Allen Ginsberg hung out. It's now a clothing store. 179 Macdougal used to be a cabaret where Barbra Streisand and Woody Allen performed. Now it's a dry cleaner. 176 used to be a salon / tea room for the literary set. Now, it's a laundromat. You get the idea. This used to be the prime area for the artist and bohemian set and now it's very commercial. The buildings are the same but the energy is different. Don't get me wrong, Macdougal is still a very village street -- it has just lost a little bit of it's bohemian ties. I'm assuming this is because it's now a desirable neighborhood and NYU kids are always around.
Macdougal takes a brief reprieve as it turns into Washington Square West but it turns back into Macdougs after the park. Most of the block is taken over by NYU as its law school is on the west side of the street. Provincetown Playhouse used to be a really renowned theatre and now it's a really renowned Children's theatre -- so, if you have kids, this is the place to go. The building is really cool but I've never seen a play here as I'm not 8 years old. The only building on the block that hasn't been replaced by NYU is 129 Macdougal. It's a cool tea spot now that would be cooler if there weren't so many students. It used to be a speakeasy that forbid men entry. That must have been a sight in the 1920's: a women's only speakeasy!
South of 3rd is where Macdougal really starts to jam and still has a little bit of the vibe I imagine it had fifty years ago. Cafe Reggio is a great little Italian place that has been open since the '20's and has been featured in a ton of movies. Mamoun's Falafel (the most famous falafel joint in the city) is directly next door. And, next door to that is the Olive Tree Cafe and the Comedy Cellar. The Olive Tree is nothing to talk about, food-wise, but it's where all of the comics from the Cellar hang out in between sets so it's always pretty lively. Directly across the street from the Olive Tree is a fantastic old building that Louisa May Alcott lived in when she wrote Little Women. It looks exactly the same as it did almost 200 years ago. Next door to the Olive Tree is Cafe Wha -- it's a very famous performance venue where Jimi Hendrix, Bob Dylan, Richard Pryor and Bill Cosby all performed. A few of my friends' bands have played here and I have always had a great time.
Across Minetta Lane is a building that has always had a noteworthy business in it. It used to be an Italian Restaurant (1937) that served as the meeting place for Ezra Pound, ee Cummings and Ernest Hemingway. Then, it was a speakeasy. Now, it's Minetta Tavern. It's a very trendy restaurant that still looks very old school which is rare for trendy restaurants. I don't think the food is out of this world but I still really like the place. It's always crowded, dark and cozy. Next door to Minetta is the polar opposite sort of venue: Off the Wagon. It's the frattiest bar of all time but you can have quite a lot of fun playing beer pong there on a weekday night when it's not too crowded.
Essentially every building on this street that hasn't been torn down by NYU has a great arts-tied history. Some of that energy is still prevalent in the bars and performance venues which is great. It's a very lively street and it is, aesthetically, exactly how you would want a village street to look.