Staying at the Essex House across from Central Park Labor Day w/e
Why a two mile walk?
From your hotel limiting yourself to a two mile walk is basically eliminating anything below 23rd St or so.
If you really want a taste of NYC, you need to consider a lot more area: Chinatown, Lower East Side, Union Square, East Village, West Village, TriBeCa, etc. Places like Katz's Deli, Russ & Daughters, dell'anima, Zabb Elee, Sao Mai, Motorino, Terroir, etc. are all downtown.
Are you opposed to cabs, buses, the subway? What if the weather is bad?
Here's a post I wrote for another out of towner, maybe it will help you.
To make the best use of your time, you should try to find things to eat to/from the tourist destinations or near the tourist destinations. Our tourist destinations are spread out all around town.
Where are you coming from?
When are you coming? How long are you here? How many meals do you have available?
We don't want to recommend food that you might do better at home, but we also may have some cuisines you can't find at home...
I'd say we are pretty strong in a lot of different cuisines but not equally. Budget will makes big difference in where you can go.
Are you willing to wait for a table at a no reservations restaurant? If so, for how long?
What is your budget, per person, per meal, BEFORE tax, tip, wine/drinks/etc for your meals? It is much easier for us to help you if you give a pre-tax-and-tip figure.
Feel free to break out your budget in terms of upscale/fancy meals (and number of them) and cheaper/everyday meals.
Note that popular places tend to book about a month in advance. Most upscale restaurants serve weekday lunch (but not weekend lunch), and serve dinner Monday through Saturday, and are usually closed Sundays, though there are a few exceptions to the "closed Sundays" rule (ex: Per Se, Eleven Madison Park, Jean George).
What else are you doing while you are here? Planning around sightseeing, shopping, Broadway shows, etc?
Check out some "Only in NY" type foods while you're here: bagels and smoked salmon, pastrami on rye, pizza, hot dogs & papaya juice, black and white cookies, cheesecake, egg creams, pickles, halal carts.
Russ & Daughters (takeout, busy on weekends), Katz's Deli (from When Harry Met Sally), Papaya King etc. (not gourmet but iconic), William Greenberg's black and whites, Junior's cheesecake, egg creams from Gem Spa or Ray's, Pickle Guys, the Halal Guys (53rd and 6th after sunset), are all iconic "NY" sorts of places that are worth a look.
If you're interested in some of the places I listed above, you could do a LES food crawl.
I highly recommend RGR's self guided Lower East Side Gustatory tour but sub in Pickle Guys for Guss' Pickles and note that Economy Candy's address is incorrect:
Best NY style pizza:
We also have some of the harder to find Chinese cuisines: Henan, Shaanxi (Xian Famous Foods) and Fuzhou in Manhattan, and many more in Queens and Brooklyn (Shangdong/Qingdao and Dongbei to name a few). scoopG's Chinatown list (dependent upon where you are coming from these may be exotic or not... most places don't have Henan or Xian style food though):
You might also want to do a restaurant doing creative takes on Asian, like at Momofuku Ssam Bar, Wong, Fatty Cue, Takashi, RedFarm, Mission Chinese, Jungsik, Kin Shop, or Danji.
My favorite unique places in NY serve Xian (Chinese) food, Issan (Thai) food, organic/local/sustainable Japanese BBQ, authentic Basque (Spanish) tapas, creative diner food, pretzels, hot dogs, halal food, steak, upscale rustic Italian, Italian subs, creative Italian-American, high end non-sushi Japanese (like kaiseki), creative desserts, molecular gastronomy, mixology/creative cocktails, and creative brunches (sometimes every day of the week).
Some common tourist inquiries:
Where to Eat Near Museum Mile (Metropolitan Museum of Art, Whitney, Guggenheim, etc) on the UES:
Where to Eat Near the Museum of Natural History on the UES:
Where to Eat Near Macy's/Herald Square/Penn Station/Empire State Building:
Where to Eat Near Grand Central/Midtown East:
Where to Eat near 5th Avenue shopping / Bloomingdale's / Rockefeller Center:
Pre-theatre Dining (many of the same Times Square recs also apply):
Where to Eat Near the 9/11 Memorial:
Notable food trucks/carts:
Prix fixe lunch deals:
Best breakfast/brunch in NYC:
It is (IMO) at the Breslin, Locanda Verde, Shopsin's, Clinton St Baking Co., or Minetta Tavern.
Best bagels in NYC:
Summary: the freshest bagels are the best; bagels don't age well at all. Focus on the smoked salmon instead. Preferably at Russ & Daughters! Featured in shows such as No Reservations and Louie!
I'm fond of red onion, capers, regular cream cheese, and tomato on mine. Try a few smoked salmons before you settle on one, they're surprisingly different (and lox is not the same as smoked salmon, because lox is salmon cured in salt brine, and most people actually prefer the more modern, Nova-style smoked salmon). You can get a mini-sized bagel sandwich at Russ & Daughters, too, if you wish. Takeout only.
If you like the idea of RGR's self-guided LES tour above, check these out, too.
Maybe scoopG's self guided Chinatown tour:
A West Village food crawl
Used to live next to the NYAC.
You are lucky to have one of the best premium bakeries/cafes close by in Petrossian. Almond croissant is a must there (before 12pm on weekends, they always run out).
You also have a 1 michelin starred Austrian weinbar across the street in Seasonal, more modern than cozy but still casual.
For coal oven pizza, Angelo's on 57th and 6th Avenue and Don Antonio's a few blocks down for that fried starita.
Viet/Thai go west to hell's kitchen, won't we as good as queens but still good and relatively inexpensive.
Soup Dumplings at Joe Shanghai are a block and a half west on 56th St. Ippudo ramen is several blocks south.
I almost never do casual italian as it is generally on of the most overpriced and disappointing things in NYC, but serafina is a couple blocks away. For fine italian, Quality Meats just opened up Quality italian on 57th and 6th and everyone I know who has gone there raves about it.
I would not limit yourself by miles walking but rather what is easily accessible via subway (E/B/D and F are all within a block). That opens up flatiron, chelsea and soho. Great casual American can be found in the bar rooms of the NYC restaurant empires (notably Craftbar).
"I almost never do casual italian as it is generally [one] of the most overpriced and disappointing things in NYC...."
Sounds to me like you have not been to Le Zie, Frankies, Rubirosa. among others. Maybe it's a downtown versus uptown thing, as I often am disappointed by the uptown options (or maybe I just don't know where to go uptown).
OK Kathryn, the sneakers will be on and I'll be on the move! thx for the great suggestions and links! My printer will be getting a workout in a moment!
Will be in NYC 4-5 days thur-tues Labor Day w/e. Just back from London where I left most of my $$$ dining but, I'll worry about that, next month!
More inclined to enjoy the warmth, charm and character of a neighborhood hangout. And of course, good food and drink.
IMHO the best $31 you can spend is for an MTA subway/bus pass for a week. If you take 13 trips on a subway it will pay for itself. Having visited many times and used this transportation, it eliminates many $$ in cab fares and lets you explore the area. The buses can be fun to ride back above ground and see what you miss on the subway. Maps are available at stations with a service area--it is safe, quick, comfortable, and convenient--- part of why NYC is such a fun destination. You will still walk and get exercise. Passes can be bought a the stations with a credit card (some but not all take cash also). There are also stores that sell them but they are not as convenient as the stations since you've got to go into a station to catch a subway. You can do a search for New York City Subway Map and see the system and get a good idea for your trip planning before you arrive. Have fun! Kathryn's point about "why walk" is good advice. Unlimited travel on subways and buses for 7 days is just a wonderful deal...it pays for itself if you save a couple of cab rides and gives you great flexibility.
I take the subway all the time in NYC, but walking is also great. In fact, it is my very favorite form of transportation worldwide, and I always prefer to walk home after dinner if at all possible. (I really don't want a bus ride after.) Generally, when I visit New York, I can always find wonderful restaurants for dinner within a 30 minute walk of where I am staying. Central Manhattan is quite safe at night for after dinner strolling.
There is nothing wrong or dangerous about taking the subway back to where you are staying from other places. I'm just saying it's not just the way I prefer to end a wonderful meal in Manhattan, and I am hardly an unusual person.
You are about 1 block from Columbus Circle and the subway station. Please see my post on: http://chowhound.chow.com/topics/913599 for an interesting area in the West Village(there are many great areas). You're a straight shot to the Christopher St. Station (on the downtown line 1 train) which is just about a block from Il Cantuccio a wonderful Tuscan Bakery. Enjoyed that area with my wife. A lot of great food and people watching---cheese, pork store, breads, and pizza. Kathryn has great information on this topic as well as others.
If the weather is nice, few things capture the flavor of NYC like a picnic in Central Park. Walk over to the food hall at the Plaza Hotel, which is a little like a NYC food greatest hits, and pick up lunch (a lobster roll from Luke's, or a funky sub from No. 7, or a traditional French baguette sandwich from Pain D'Avignon, and maybe a cupcake (or three) from Billy's) to take over to the park with you.