I'm going to New York for a long weekend in September. What would I regret not doing during my time in NYC?

I would definitely see a Broadway show if you are into that sort of thing. Some of the most fun I had in NYC was walking around Chinatown and Little Italy. There are also a lot of museums and cathedrals to visit if you want to do that. Then of course there’s all the other landmarks like the Statue of Liberty, Ground Zero, and the Empire State Building.

Haggle with Chinatown vendors.
Go to Times Square.
Take a picture of the Wall Street charging bull.
Go to the museums.
Go to Central Park.
Ride the subway to nowhere in particular.

There have been some extensive answers to this question many times. Search on NYC and see if you can find them; otherwise, I will try to.

Going to see jazz at Micahel’s Pub. I am envious. September is a perfect time to be in NY.

Circle Line Cruise could be fun!

I was in New York for just a few days over Thanksgiving last year, and despite time being tight, one of my most treasured memories of my trip was when I had made plans to meet a friend at the Museum of Modern Art and, via miscommunication, arrived an hour early. I bought a hot dog from a stand and sat on the steps of some church along 5th Avenue (just Google Mapped it – St Thomas Church on Fifth Avenue) and watched people go by.

Times Square at night sounds touristy, but is a must. Spend some time walking around Central Park, too… it’ll be lovely in September.

You might find goNYC useful.

I personally would not put the Empire State Building at the top of my list.

I find the Status of Liberty and Ellis Island more interesting.

If you appreciate art the Metropolitan Musem of Art is fantastic. I think admission is $20, but if that is steep for you, you can offer less. Just say you prefer to pay $10 (or whatever you are comfortable with) and there will no problem.

The new Planetarium at the Museum of Natural history is very good also.

Defintely walk through central park (the met museum of art has a terrace where you can look ove rthe park, very nice). If you decide to shop, I recommend Bloomingdale’s. Although, Macy’s I think is still the largest store in the world, but macy;s is more chaotic. No tax on clothing under $150 or maybe it is $120?? In NYC.

Do ride the subway at least once. Get off in Grand Central Terminal (featured in so many movies) go to themain part of the terminal, super high ceilings. I think they changed the flipping sign to digital that showed all of the trains coming in and leaving, a little bit of history lost. I think there is still a small museum of transportation there (an annex to the main museum in Brooklyn) which gives you a little dose of the subways history, and some souveniers you can buy like subway map umbrellas and things. From Grand Central there is a fast train over to Times Square.

Go to a deli and have a pastrami sandwich. My husband likes Stage best, but Carnegie is probably the most well known, but Katz’s is the one from When Harry Met Sally. Oh, MOMA is nearby Stage and Carnegie if you go there. There is free adission on Friday night from 4:00 to 8:00 from what I understand, you can look for details here http://www.moma.org/visit/plan/index#ticketing

Walk around SoHo

Oh, if you are one of those no gluten, natural people, Baby Cakes brownies are not to be believed!! http://www.babycakesnyc.com/

Walk across the Brooklyn Bridge!

Have your picture taken,one one knee proposing marriage to the Naked Cowboy !
Buy yourself a 3some with some Times Square hookers !!

Eat as many times, in as many places, as many varieties of
unfamiliar food as you can; nosh, instead of sitting down to meals. You’ll keep yourself fuelled and you’ll experience many cultures.

You have to atleast consider the following:

Go very early to the Rockefeller Center on Friday for the (NBC) Today Show live broadcast. Across the street on Fifth Avenue is St. Patrick’s Cathedral.

Walk up 5th Avenue to peruse the high class, high-fashion, designer stores and boutiques. If you need to use the restroom by this time, go to Trump Tower at 5th Av/E56 St. Head-up north to Central Park, along the way are F.A.O. Shwartz Toy Store, The Plaza Hotel, the Apple Store.

Head westward to Columbus Circle and take subway down to Wall Street. Places to visit are the World Trade Center – ground zero, South Street Seaport, NYSE, Trinity Church, Battery Park. Staten Island Ferry Terminal.

Hop on a Free Ferry ride to Staten Island to get a vista of the NYC Skyline while the ferry crosses the New York Bay, passing right infront on the Statue of Liberty. Stay on the ferry for the trip back to Manhattan.

Trek back northward to Chinatownand spend the afternoon rumaging through Canal Street stores. Dinner time at Little Italy is pricey but walking through Mulberry Street is one of the Must-Do’s.

Threafter, its a either East Village or Greenwich Village for drinks and hanging-out.

Nightlife are plentiful in Chelsea/Meatpacking District.

Spend a few hours after midnight in Times Square and if you get hungry, head on over to Japantown or Koreatown where they have 24-hour Sushi joints and Hibachi restaurants.

Trying to see everything is exhausting, keep a list of resting spots where you can simply sit down for free. (http://www.bryantpark.org/, Central Park, the libraries, Battery Park all come to mind)

You will have a GREAT time!
Here’s one of the previous threads.
http://www.fluther.com/disc/68006/what-isare-your-favourite-things-to-do-while-on-a-weekend/

to echo @jaytkay‘s point, plan your pace . . . map out where/what you will visit and nearby Restrooms, you will appreciate knowing where you can “rest” as the need arises.

Make sure you wear comforatble clothing and shoes.

Dirty water hot dog vendor across the street from battery park yum! My favorite part of NYC.

I thought it would be corny but the Circle Line boat tour that takes you all afternoon along the river and around the island was the highlight of my visit there. Great sights, great history.

The Met museum (of course) I spent three days in a row there in bites of about 5–8 hrs each, so worth it.

Moto bar in Brooklyn. Trust me on this one for atmosphere and excellent food, it’s small but worth the cramping. Reminds me of a place in SF actually.

uh, not walking past a smoking SUV in a theatre district on a quiet evening in times square.

Statue of Liberty…there is nothing like seeing it from the water when you take the ferry. And seeing the city from the water. It will imprint your memory.