for me, for whatever reason, forever remains a Fall destination/getaway (I generally recommend late Sept to late Oct). Sure I’ve visited in every season, but my preference is always for Autumn. The heat and tourist hordes (oppressive in Summer) are gone, the locals are slightly calmer, and the hooplah (+cold) of Xmas and Winter are still somewhere in the future.
So as I plan a mid-Autumn getaway here is…
MY NEW YORK LIST 
The Ace Hotel: http://www.acehotel.com/newyork hipster central with great lobby scene and great coffee in that lobby… :) p.s. make sure to pack your mac.
Americano: http://www.hotel-americano.com/ ultra-modern latin/japo cool in Chelsea. The rooftop pool was quite the scene this last summer.
Crosby Street Hotel: http://www.firmdalehotels.com/new-york/crosby-street-hotel my favourite hotel in Soho. A proper English tea is available.
Gild Hall: http://www.thompsonhotels.com/hotels/nyc/gild-hall great style, crisp sheets - think stylish hunting lodge (and great rates on weekends).
Hotel on Rivington: http://www.hotelonrivington.com/ for the view over, and location in the LES. and the show-off showers.
NoMad Hotel: http://www.thenomadhotel.com/ Jacques Garcia strikes again.
6 Columbus: http://www.thompsonhotels.com/hotels/nyc/6-columbus need to be near Central Park? this is my fav.
The Standard (High Line): http://www.standardhotels.com/high-line THE hotel for the views and the celeb watching.
Wythe: http://wythehotel.com/ I love this place in Brooklyn. Gorgeous.
Abraco: http://abraconyc.com/#home almost never open, but very good coffee when they are.
An Choi: http://www.anchoinyc.com/ go for the drinks and ambiance, Hanoi bunker style in the LES.
Barrio Chino: http://www.barriochinonyc.com/ tacos and tequila deep in Chinatown.
Bathtub Gin: http://www.bathtubginnyc.com/ kinda hidden speakeasy, yes with a bathtub.
Bottino: http://www.bottinonyc.com/ another great resto (this one Italian) popping up in the Chelsea Gallery District.
Bouchon Bakery: http://www.bouchonbakery.com/ nice pastries to go near Central Park.
Bugs: http://therealbohemian.tumblr.com/post/29078680506/bugs the smallest sushi bar you ever did see.
Dirt Candy: http://www.dirtcandynyc.com/ my go-to for inventive vegetarian.
Doughnut Plant: http://doughnutplant.com/ just go ok? they’re like little deep fried, creme filled orgasms… ;)
Fat Radish: http://thefatradishnyc.com/ funky, clean, simple, really good.
5 Leaves: http://www.fiveleavesny.com/ the best burger in Brooklyn, and probably all NYC.
Frej: http://www.frejnyc.com/ hidden, awesome food, great indie vibe.
Gimme Coffee: http://www.gimmecoffee.com/static/community_stores.aspx love the coffee here, I go to Mott St.
John Dory Oyster Bar: http://www.thejohndory.com/ fresh oysters is what I go for.
La Esquina: http://esquinanyc.com/# the mexican here is very respectable, great location between Soho, LES, Nolita for doing other stuff.
Locanda Verde: http://www.locandaverdenyc.com/ very good Italian. and very buzzy.
Luke’s Lobster: http://www.lukeslobster.com/ the best lobster roll I ever had I think.
Murray’s Cheese Bar: http://www.murrayscheesebar.com/ cheese cheese cheese! and craft beer.
9th St. espresso: http://www.ninthstreetespresso.com/Ninth_Street_Espresso/Locations.html attitude laden service yes, but the espresso is worth it.
Num Pang: http://www.numpangnyc.com/ no frills, great sandwiches.
Ovest: http://www.ovestnyc.com/ “Naples style” pizza and pasta in Chelsea.
Public: http://public-nyc.com/ Brunch is the meal here.
Red Farm: http://redfarmnyc.com/ love the very flavorful “fusion” here (and I’m not a fan of fusion).
Rubirosa: http://rubirosanyc.com/ my fav pizza and pasta in town.
Schiller’s Liquor Bar: http://www.schillersny.com/about.php say what you will, but I like this LES standby.
Smith and Mills: http://smithandmills.com/ miniscule TriBeCa boite worth the hunt.
Taim Mobile Truck: http://www.taimmobile.com/ best falafels!
Tartinery: http://www.tartinery.com/ sleek, french and tasty.
Tortaria: http://tortaria-nyc.com/ the latest Latin “trendy” food.
Txikito: http://www.txikitonyc.com/ tapas Basque style. And very good.
Aerie Ancient Baths: http://ancientbathsny.com/ relax go do it…
Aesop: http://www.aesop.com/usa/ustorelocator/location/map/ the Nolita location is the one I love.
All Good Things: http://allgoodthingsny.com/ a gourmand’s food hall in TriBeCa that has locals salivating.
Flight 001: http://www.flight001.com/ a must for every jetsetter.
High Line: http://www.thehighline.org/ for an early evening stroll.
Le Bain: http://standardculture.com/lebain for late night debauchery.
Lost Weekend: http://www.lostweekendnyc.com/file/HOME.html espresso, and gallery, and stuff…
New Museum: http://www.newmuseum.org/ oftentimes great contempo art and a view (on weekends only)
OHWOW: http://oh-wow.com/book-club/ a miniscule bookshop
Sleep No More: http://sleepnomorenyc.com/ haunted house/theatre/dance piece.
Treasure & Bond: http://www.treasureandbond.com/site/ 100% of profits go to charity. awwww.
V Files: http://therealbohemian.tumblr.com/post/21053856123/vfiles-gallaghers ever wanted to find a 1967 issue of Playboy? It could be here.
A FEW TIPS
PORTER AIRLINES is constantly offering 50% off sales from Toronto to Newark Airport. They also just opened a LOUNGE for all passengers next to their gates at Newark Airport so they are a very popular choice for downtowners. Air Canada and Westjet often match the discounts.
KEEP in mind 2 things: 1. There is no US Customs Preclearance at Toronto Island, so all passengers are processed at Newark (Crazy long lines between 2pm to 9pm) 2. All flights to New York (whether Newark, LaGuardia or JFK) tend to be subject to air traffic delays. I have NEVER in my 20 yrs of flying to NYC ever been on a flight that departed AND arrived ONTIME. My tip is earlier in the day, the less late. Once it snows - just pray…
HOTEL RATES in Fall tend to be a fair bit higher than in Summer so to get lower rates I usually book thru Quikbook OR if you can bear to wait until the day of, and aren’t married to your hotel choice, the HOTEL TONIGHT app (iPhone, Android) has been very successful for me. (Just check there are no conferences in town).