The Tunnel

SoHo, Chelsea, the Flatiron district would be cool places to check out. If the weather is good, it's a cool area to walk around. There are some shops/restaurants on Broadway between 14th and 23rd. Washington Square Park is a cool park near some neat NYC neighborhoods. Usually they have music, fairs, etc going on there. It's between 4th and 9th. All of this area is cool because it has much more of a community feel than midtown, which is all businesses, restaurants, etc.

If you haven't been to the Times Square/Broadway district area and you have some time, that would be a good place to walk around for an hour or two. You'd have to take a cab, but it's probably 15 minutes and $20 each way, tops.

The Financial District is decent during the day, but quiet at night. If you want a good laugh, go by that Zuccotti Park at night and check out the protesters.

come on man, nyc is one of the safest places around now!

Going to see the 9/11 Memorial is an absolute must. Very sobering, but pretty much a requirement for all Americans in my opinion. If you are down there, the old Downtown Athletic Club building is very close to there. It's been converted into condos I think, but they might still have the Heisman bust in the lobby, that would be neat at a football fan. I used to belong to the DAC prior to 9/11 and it was a really cool place, used to visit the room where they presented the trophy all the time.

Other places in lower Manhattan that could be fun..
Bars:
There is a string of bars down on Stone and Pearl Streets that that really come alive in the spring for happy hour..A couple are called Ulysses Folk House and Stone Street Tavern.

Food:
BLT Steak is right by the WTC area, and Dillon Prime is a litte but north of there near Canal If you are looking for good Italian, there is a GREAT place called Ecco, on 124 Chambers Street. The Lobster Fradiavlo is absurd. There is actually a pretty decent wings and sports bar right next to that called Mudville 9.

Let me know how it goes.

comedy cellar in greenwich village...2 shows on weeknights, 3 on Friday, 4 on saturday.
they get a ton of talent.
aziz ansari, louis ck, dave attell, judah freelander, colin quinn, jim norton all regulars...this is the place a ton of guys try out their material and just practice stuff...it is where chappelle and chris rock are known to drop in.

each set has 4-5 comics and they usually keep pretty up to date on their website, although they have a lot of drop-ins...it is cheap, and small spot, so really cool....food in restaurant above is also good.

so much good food as well...shake shack is pretty sweet burger/shake place that is all over...if you are looking for something quick.

Go see a show at UCB if you get a chance!

you can always visit the lovely Menlo Park Mall in Edison

speaking of comedy clubs, Carolines in NYC is nice depending on who his there. The food is decent as well.