Our New York City Walking Tour

If you love to walk, and you’ve always wanted to visit New York, I have the self-guided tour for you.

People have been coming to New York to visit since the Dutch settled here. They want to see the buildings, the culture, the places recognizable from movies, and experience the food. I have a tour, created by Jack and myself that is perfect for first-timers. It accomplishes everything you need in a day, and at the end, you can eat whatever you want because you will have walked till your legs fell off.

Take the 6 train to the Brooklyn Bridge. All the way down there. You will get a sense of New York from our subway trains, but you will be on the cleanest, and most gentrified line so you need not be afraid. The subway trains of the 1980’s have long since been replaced.

Walk exactly half way across the bridge. You will know you’ve done that when the Brooklyn-bridge cables have dipped all the way to the railing and will soon begin to climb upward again toward the historical arches. From here, you can see the statue of liberty and take beautiful pictures with many city views. Now walk back towards Manhattan.

Straight in front of you, is City Hall and it’s park. You can cross it and see the members of the financial districts sipping Starbucks and reading the Financial Times. Cross Chambers street and you will find yourself at Ground Zero. Everyone wants to go there, and this will get it out of the way. If you see Century 21 across the way, do not go there. Although the discount shopping is unparalleled, you will not be able to lug it the rest of the way. There is a cemetery with iron bars around it. For months after the towers fell, this fence was covered in tragic, hopeful, inspiring and supportive banners and messages.

Head north, past the post office until signs begin to turn to Chinese. Around Grand Street (a few blocks after would be alright), turn right (heading East) for about three blocks. You will find yourself in another country. There is even an HSBC with sweeping roofs and a McDonald’s with the famous sign in Chinese. Canal Street has great shopping. You can get a real or fake Coach bag for next to nothing.

Find Mott Street and head North. You will pass the tiny vestiges of Little Italy, now swallowed by trendy neighborhoods and China town. At Spring Street, turn right (east) and walk three blocks. If you are very hungry, Lombardi’s , on the South side of the street, serves some of New York’s oldest pizza. I went there once with someone who had been ordered from Ohio to bring back slices wrapped individually in tinfoil by the chef. “He knows how.” Or, you can go to Rice to Riches, on the North side of the street, where you will be entranced by the space-modern décor and the never-ending selection of Rice Puddings. Even the dishes and spoons (look like shoe horns) are great.

Once back on the street, go back to Mott Street and go North (right out the door of Rice to Riches and then Right on Mott). Walk north. You are now in SoHo (Stands for South of Houston). If you can slog your way through the trendy folks who are paying twice what the rest of us are for rent, you can admire all of the fancy boutiques.

Cross Houston and head a few blocks west to Sullivan Street. As you walk up it, you will see the Peanut Butter Company. They have different flavors of peanut butter and feature The Elvis. It was the King’s favorite sandwich of peanut butter, banana, honey and bacon. It’s so much better than it sounds.

Continue North. You will hit West 4th st/Washington Square Park. There, in the South West corner of the park, you will see the chess players from Searching For Bobby Fisher (the movie). Don’t play them. It is a New York tradition for them to scam you and they WILL take your money.

Here, cross West 4th and turn Left on Macdougal (you will be walking South but only for a block or two). Past Ben’s pizza and Café Reggio (where I once had so many $2.50 lemonades that the lady started giving them to me for free. It is literally lemon juice with a sugar pot in the middle of the table. You just season to taste). Past The Comedy Cellar where I highly recommend you come back in the evening because it is great, and turn right onto Menetta Lane. There is another tiny left there that I think is also Menetta lane. You are on the smallest named street in Manhattan and one of my favorite places in the city.

On sixth avenue, cross west onto Bleeker st. There you will find Amy’s bread which makes some of the best sticky buns, and breads, I have ever bought. Then Murray’s cheese, where I worked for six months. The cheeses selection is phenomenal and the girl who ages the cheese in the five temperature/humidity controlled caves, Zoe, does an amazing job with each cheese. You can taste any cheese that is not sold by the each so take a number and see what looks good.

John’s Pizza is another block up Bleeker. It is famous and very good. I have heard that tourists come far and wide to try the pizza. I have also heard that they do so because it has been made with jarred tomato sauce and therefore tastes familiar to them.

Last stop on this street, is Ottomanelli’s on the left hand side. It is what remains of old New York butcher shops. You don’t have to go in if you don’t want. I mean, you can’t really drag a roast with you. But just appreciate the fact that this place seems frozen in time. At Thanksgiving, they have an elaborate system where you order your turkey and they write everyone’s names in black marker on brown paper bags that have been taped to the wall. When you show up and get your turkey, where you are on the board indicates to the guys what size you have ordered and what breed. They cross your name off with a long ruler that has a marker taped to it. It’s a mad house so I won’t be doing it his year, but if you ever move here, join the tradition at least once.

Now, walk back to sixth avenue. You have to go left out of Ottomanelli’s. Cross it, and head north (left). You will see the West 4th basketball courts. You might recognize them from Mountain Due Red commercials or movies about New York from the 1980’s and early 90’s. Many great players were discovered here and for a long time, being acceptable to play there said a lot about your abilities.

Continue north one block and turn right. You are going back to Washington Square park.

Walk through the arch on your way out of the park. If you are lucky, someone will have whispered “butts, smoke, trees” in your ear. You have just been offered drugs. As you pass through the arch, think about the history of New York. It was built to symbolize the divide between the industry and business of uptown and the artistic vibes of downtown. Now, NYU graduates pass underneath as part of their commencement ceremony.

Turn Right and head east towards Astor Place. There is an enormous black cube in the center. Turn it. Don’t worry, you can. I bet you it’s possible.

Then north. At 12th street, turn left (west) and stop in at The Strand. It is quite possibly the largest bookstore in the world and although you can’t ever find what you’ve gone in for, you always walk out with your arms fully loaded.

Further north, about two blocks, you will see Union Square. Have a seat and watch the crazies go by. Jack and I once saw a woman clutching a tree branch as if it were a picket sign. She wandered around yelling at people and flashing them her nether regions. From far away, it was highly amusing. Also take not of how easily New Yorkers can ignore such a strange occurrence. This is also the home of our largest Green Market. Open Monday, Wednesday, Friday and Saturday.

Now, you’ve rested a few minutes, go to the north-west corner of the park and walk North on Broadway. At 23rd Street, look around. The building at 23rd between Broadway and 5th Ave should look familiar because it the most blown up building in modern movies.

Madison Square Park is home to the Shake Shack. Hungry? They serve one of the best burgers in New York and shakes and custards to match. The line is so long though, that a Shack Cam was installed so that you could check on it from your office before racing down to get online.

Moving north, walk up 5th avenue and take in the shops. There are more businesses than stores this far south, but you will pass the Museum of Sex and the Empire State building. At 42nd Street, you will see the New York Public Library with it’s famous Lions out front. Remember them from Ghost Busters? On 42nd, turn left (west) and walk passed Bryant Park to Times Square. You can walk up if you’d like, it is very crowded. Here, you can by 10 I Love NY T-shirts for $7.

As you meander, be sure to be back on 5th Avenue by 51st street to see Saks (the fancy department store) and St. Patrick’s Cathedral. Here you will also see the luxurious stores. Louis Vuitton, Coach, Cartier, Harry Winston and finally, at 59th st, FAO Schwartz. Go inside and pass out among the fluffy dogs in the front. Or take a look at the giant piano from the movie Big. It was removed for a while, but has since been given it’s own section and designated dancing musicians.

Now, you are safely at Central Park. If you still have any strength left in your jelly-legs, check out my Central Park-Museum mile tour. Otherwise, crab a cab and head to your hotel to rest for your theater/dinner plans. You have walked at least six miles today, seen three countries and several New York cultures, and you deserve it.