@Double Don: Try googling P. J. Clarke's, where Sterling Cooper had a party. I believe there are 4 locations.

It's certainly not from MadMen days, but there's a bar in the East Village (E. 6th btw 1st Ave and Ave. A) called Death and Company, which is an old Prohibition term. It makes "real" drinks, not even vodka drinks, with old and artisan ryes, rums, gins, all kinds of bitters, potions, etc. From like the really old days. But it has that "drinking man's bar" feel to it and might start off the night quite well.

And how about Keen's for steak and chops, or Smith and Wollensky's?

If you could somehow be transported back in time to MadMen days but with a 2009 pocket, check out of the sleazy Times Square Hotel, book a suite at The Plaza or Pierre, spend the evening at The Playboy Club, and the following morning skip the conference and get your ass over to the nearest Real Estate office and buy up any Town Houses for sale. Then go home and wait.

Sort'a MadMen-ish...but if this is your first time:

Walk through the lobby of the Plaza at Central Park South and Fifth Ave. Right behind it is Bergdorf Goodman (make sure you go upstairs...)...Walk through Grand Central Station...1/2 a block away have a cheap lunch (a bargain) at Patrick Conways ...up a few blocks and trek through The Roosevelt (Don stayed there) and then a few blocks south to the iconic Seagram's Building and the 4 Seasons Restaurant.

These are all in close proximity on the east side. You will walk down Madison and Lexington Avenues and at some pioint pass the Waldorf-Astoria. Hilton ran it, and the Plaza.

I think Pete and Trudy live either @ 38th or 32nd.
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Stay away from Bloomingdale's, the Hard Rock Cafe or any other spot that has people outside with shopping bags.

2 cocktails in the Oak Room Bar will cost you $25, and well worth it.
If you are so inclined...stop for a drink at The Townhouse...opens at 4.

Dress well and DO NOT look like a tourist: if anyone asks...tell them you are from Mt Kisco.

Addresses and info on all these places are available online. Have fun!

Travel over to Brooklyn and go for a steak at Peter Lugers.

Go to Keen's Chophouse.

Gavin - Great pointers.
Pete & Trudy live off 5th Avenue @ 86th Street.

Not very MadMen-ish, but have a drink in the Rainbow Room (top of Rockefeller Center).

We had Thanksgiving dinner in the Rainbow Room. I think you will really like it there.

Welcome to our fair city, DoubleDon! Check out this great article:

http://newyork.timeout.com/articles/own-this-city/77796/mad-men-walk

Time Out NY is a good website to look up other random things to do as well. Also Yelp.com is great for restaurant reviews, etc.

I recommend Bemelman's Bar on the UES for a cool, swanky, retro place to grab a drink. It's located in the Carlyle Hotel on E. 76th. Very MM.

http://www.thecarlyle.com/dine4.cfm

I agree with Zabadu on Peter Luger (unless you're a vegetarian). Classic. I'm pretty sure they don't take credit cards so be aware of that before you go.

Wonder where Gail Klein is? I know she used to live in Manhattan and worked at Saks. She might know some good places....Gail, are you still around???

Love reading all these great suggestions (stuck waaaaay down here in the Midwest)....going to keep them all in mind to use someday when I get to finally visit NYC.

If you're lucky enough to get tickets, see the Bye Bye Birdie revival. John Stamos is Albert (Dick van Dyke's role in the Ann Margaret movie).

Be sure to let us know how your trip goes and what you actually decided to do! My first NYC trip was 25 years ago and I still remember it.

I'm here, SC Fan!

Why don't you go to the original P.J. Clarke's on 3rd Ave. around 50th St. where the Maddicts had a party last December?: Then, you can walk on Madison Ave. between 50th and 51st Sts. and see the Advertising Walk of Fame. Go to Grand Central Station and eat oysters and drink martinis at The Oyster Bar. Sorry, folks, but The Rainbow Room closed down last year. La Grenouille is still there, if you want VERY expensive French food, Mad Men style. If you're really adventerous, walk through Central Park into "The Ramble," the notorious gay meeting place, where Sal went cruising. Then go down to Greenwich Village and hear some live music at the Village Vanguard and pretend to be a beatnik.

Have fun!

P.J. Clarke's is on 55th St. and 3rd Ave. This is where Pete and Trudy did the "Twist!"

Have lunch or dinner at the 4 Seasons in the Seagrams Building.

The Yankees play the Angels at the new Yankee Stadium, and if baseball is not your thing, you can always give Elliot Spitzer a call and cruise for some hookers at the Javits Center

You guys are awesome! I am a huge fan of old hotels so I think I'm going to try to hit the Plaza, Waldorf, Algonquin, Roosevelt, and the Paramount. Then also try to squeeze in PJ Clarks... we'll see, if I have a drink at each, I'll be flying high by the end of the night.

Love all the suggestions and will take ths with me... THANKS ALL!

I'll report back...

I can't wait to hear how it goes, DoubleDon! I love introducing people to my beloved city!

Oyster Bar for lunch--I just went with my pops when I was in town last week! SUCH good seafood and at a reasonable price. It's a jewel.

But if you have big bucks and love seafood, you must go to Le Bernadin. It is arguably the best restaurant in the western hemisphere. And attracts many of those martini power lunchers as in MM days.

hey Monte-At any bar I have ever been in the WORLD (except maybe London) everyone asks everyone else where they are from. Mt Kisco is a very nice little place (50's home of Bennet Cerf).
Perfectly respectable.

And yes, no one really gives a damn, but it is called social interaction and I find it very useful when picking someone up in a bar.

GailKlein: Oh no, I'm so sad to hear the Rainbow Room is gone.

I think it was Peggy and Ken doing the Twist in Season One - The Hobo Code. She "twisted" over to where Pete was sitting. And he shot her down.

Pete & Trudy did the Charleston.

Mt. Kisko? Isn't that where she boiled the bunny? Be careful!