NYC Tip To Tip Walk

My wife and I moved to Manhattan in the summer of 2023, not because we had to, but because we wanted to, and both work and family considerations conveniently allowed for a few-year window where we could try out the big city.

And for the relatively short time we plan on living in the Big Apple, our goal is to see and try out as much as realistically possible, including a lot of walking in NYC.

In that spirit, the week before Thanksgiving, when our daughter came home for a few days to visit, the three of us decided to try and walk from the northern most point of Manhattan to the southern tip.

This walk is fairly well known and was made famous in an episode of Broad City and is often referred to as the Tip To Tip walk, Top To Tip or even Top To Bottom walk.

Whatever you call it, the walk will end up being around 13-16 miles, depending upon the route you take, and will likely take most of your day. And energy.

I read about a few routes for walking in NYC that some people chose to take, including straight down Broadway which will run you through Times Square, or along the western side of the island which would have you skipping most everything worth seeing except the Hudson River and the shoreline of Manhattan.

My preference was to see a few important historical sites along the way, some cultural hot spots, interesting architectural highlights and almost assuredly stop for a bite or two as needed and grab a bunch of selfies with my wife and daughter as we walked through neighborhoods we had only heard about before.

And also to skip Times Square. I’ve been to Times Square, and will again as it is very hard to see a Broadway show without going through, but it’s not my favorite and would prefer to pass by without walking through whenever possible.

Working with what seemed like other people’s highlights, plus adding a few points of interest for myself and subtracting Times Square I ended up with a list of 20 spots I wanted to see as we walked what turned out to be a 16 mile trip from tip to tip.

It feels like most people start in the north and work their way south, which is also what we did, but I can see a reason or two for deciding either way. First, it is a little downhill from north to south but aside from the Cloisters most of the hills are pretty minor. And second, there aren’t as many commercial potty stops and restaurants available in some of the northern neighborhoods, so we tackled those when we knew we would already be well fed and had no need for a restroom, first thing in the morning.

On the other hand, by the time we got to the southern side of the island, there were lots and lots of people out and about, slowing us down and generally behaving as large NYC crowds often do. So if you love that vibe, great, you’ll see it in the afternoon on your walk. If you hate that energy, you may consider starting your Bottom To Top walk from Battery park and heading north to get through the most commercial neighborhoods before the shoppers and gawkers come out to play in such great numbers.

1 – The Broadway Bridge, The Met Cloisters and Morris-Jumel Mansion

Some people apparently start their walk at the 215th Street subway station on the 1 line as that is the northern-most subway stop on Manhattan. We went a little extra and started around 220th, basically the foot of the Broadway Bridge that would carry you over into the Bronx.

From there we walked towards Fort Tryon Park in Inwood which contains The Met Cloisters, a collection of European medieval art and architecture largely bought and donated by well-known financier and philanthropist John D. Rockefeller Jr. This very first segment was easily the steepest hill and climb that we had all day.

We did not stop to go through the museum as our primary goal was simply to complete the walk, so we walked by, grabbed a picture or two and swung by the Morris-Jumel Mansion in Washington Heights which may be best known as having been used by General George Washington as his headquarters for a month in late 1776.

In between our first two stops we did walk by the George Washington Bridge, which was pretty cool as we were not expecting to do so, or at least hadn’t really thought about it. Walking in NYC from Inwood, through Little Dominican Republic and then Washington Heights was a great opportunity to see neighborhoods with a very different look and feel than I have been exposed to in what little I have seen on Manhattan so far.

It was a very quiet walk in several mostly residential neighborhoods and without too many destination stops that made up our list of 20 places we were hoping to see on our tip to tip walk.

2 – Hamilton Heights, Apollo Theater, Columbia and St. John The Divine

Next up on our list was the Hamilton Grange National Memorial or simply Alexander Hamilton’s old house. Yes, that Alexander Hamilton. And yes, it is Uptown, it is all very sad, but such a great musical! If you pay attention, or think about many stops with a broad view, the Top to Bottom walk on Manhattan is almost a Hamiltonian walk, he shows up in many places!

Pro Tip: Not that I am a pro, but this could be important info for first time NYC Manhattan island walkers… The Hamilton House National Park has a clean restroom available to the public! Make sure to check hours before you plan your walk.

Leaving Hamilton Heights we walked into Harlem, which again has a very different energy and architectural aesthetic than many of the blocks we had walked so far. And of course, if you are in Harlem looking for iconic and historic destinations then The Apollo Theater is a must.

I saw a few other blog posts and articles about restaurants that looked good for lunch but we weren’t looking for a sit down restaurant as it would slow us down and we were worried that we wouldn’t want to get back up to start walking again.

After finding the Apollo we veered pretty hard west to make sure we got a chance to step into the courtyard at Columbia University, which was way nicer than I had ever dreamed. I don’t know why, but I really thought it was going to be gray and maybe a little run down. Instead it is really pretty and looks as nice as any suburban private liberal arts school you can think of!

One interesting note about Columbia is that it was established in 1754, before the American Revolution, as King’s College on the grounds of Trinity Church in lower Manhattan, it was renamed after the revolution and later moved to its current spot in the late 1800’s. One of its famous students? Alexander Hamilton.

One last stop on the north side of Central Park before we head south into the Upper West Side was The Cathedral Of St. John The Divine, sometimes referred to as St. John the Unfinished, one of the world’s largest churches. It seems unlikely that the church will ever be finished, as the ground under it proved to be less than ideal for such an endeavor. Plus the change in architectural style partway through construction probably didn’t help the situation either.

Across the street from the church and its grounds is a stop that many people add to their Tip To Tip Manhattan walk, the Hungarian Bakery. We didn’t. The line was out the door and partway down the block and we were not interested in waiting in lines.

3 – UWS, Lincoln Center, Columbus Circle, Central Park and The Plaza

As we continue to head south into the Upper West Side we have already walked over 100 blocks and almost seven miles! It is really weird to me that when you are at the midpoint of the island, north to south, you will still be pretty high up in the Central Park area, it’s a much larger island than many people think.

There were not very many destination spots on our list that we expected to see in the Upper West Side, but at the same time there were just continuously beautiful buildings and iconic shops all up and down Amsterdam Ave and Broadway.

And lunch. So many options for lunch. We opted for sliced pizza, easy in easy out. We were really trying to limit how long we sat down because getting back up and starting to walk was already getting difficult!

One of our destination spots once again was much larger and much nicer than I had expected. I thought Lincoln Center was a music hall. Singular. One large auditorium. Nope. It’s a complex that really needs to be visited to be appreciated.

On the other end of the expectation spectrum was Columbus Circle, nothing much to see here, but there is a ton of foot traffic, a lot of energy and a seemingly equal number of food carts. Oddly Columbus Circle is used as the geographic center of NYC so when you are mapping on Google or wherever and you see how far it is to drive from Point A to NYC, you are mapping to Columbus Circle.

Many people choose to continue down Broadway at this point, but in our goal to avoid Times Square we scooted along the south side of Central Park and then turning south on 5th Ave while passing in front of The Plaza, a pretty iconic hotel which has been made famous in a small number of tv shows and/or movies.

By the time we walked by the Plaza we had walked just over 10 miles.

4 – Midtown, 5th Ave, Rockefeller Center and The Empire State Building

We are well over half way now but still have 5 or 6 miles to go, and we are just now leaving the south side of Central Park! Again, my mental map of walking in NYC and Manhattan was soooo wrong!

While the miles may be slowing down, the attractions and destinations are really picking up on the southern third of the island. Our initial plan was to walk down 5th Avenue until we crossed Broadway and then follow Broadway for the duration, but there were so many people out that walking with any pace and trying to stay together simply became more difficult than it was worth, so we zig zagged over to 6th Ave to walk a few blocks and allow the pedestrian traffic to clear out before getting back on to Broadway.

But not before we got to Rockefeller Center! Did I mention we were walking the week before Thanksgiving? And that the Rockefeller Christmas Tree had already been brought to the square, covered in scaffold as it was being decorated? So many big brands had already put up their holiday decorations on the exterior of their buildings that it was simply fun to walk a few blocks just checking them all out.

It had been our intention to swing by Bryant Park to see the Winter Market, which always gets super high rankings and reviews, but with our switch to 6th Ave we missed it and didn’t swing back over to 5th until we hit 34th Street so we could see the Empire State Building. I’m a real sucker for Art Deco buildings so this was right up my alley. I also love the Chrysler Building, but chose not to include it on this trip since it would have taken us a few blocks out of our way, and I was already tired.

As a way to make ourselves feel better about missing the Chrysler Building and Bryant Park and still having about 4 miles to go, we stopped at a little hole in the wall for a snack and some water to help power us through the rest of our walking challenge, because the legs were getting pretty tired by now!

5 – Lower Manhattan, Union Square, Trinity Church and Battery Park

As we were still walking south on 5th Ave it wasn’t until we walked by Madison Square Park that we hit Broadway, which would take us the rest of the way to Battery Park at the southern tip of Manhattan.

On the south side of Madison Square Park is the Flatiron Building, a timeless classic featured in photographs around the world since it was built in 1902. While it was partially to mostly covered in scaffolding due to it’s being under construction while being converted into condos it was still worth the effort to stop for a quick selfie.

From there it is only 5 or 6 blocks to the north side of Union Square, one of my favorites due to its large and frequent greenmarket or deluxe farmers market. Lots of fruit and vegetables, artisan breads, cheese, pastries, small batch liquor, meats and even some hand made crafts, always fun to visit even if you aren’t buying.

From there keep heading south on Broadway towards City Hall and you’ll pass Strand Bookstore, often referred to as one of NYC’s best and most beloved independent book stores. We did not stop as we feared we would never get started again.

By the time you pass City Hall you will be only a block away from part of the World Trade Center complex. We felt up to it and detoured one block west from Broadway, passing the Woolworth Building, another of my favorites, in order to see The Oculus and a few of the newer towers including One World Trade Center. And then back around the block to get onto Broadway again.

In another 5 blocks or so we passed Zuccotti Park which garnered a lot of attention back in 2011 as the site of the Occupy Wall Street protests. I was very much expecting a green grassy park instead of the concrete heavy and stepped multi-level space and again found myself realizing how little I knew about many of the stops on our tip to tip NYC walk.

The blocks are a little weird this far south in Manhattan, but in only another few blocks is Trinity Church, one of our stops that I was very much looking forward to. Not only because it is so close to the end, but also because it is the resting place of the Hamiltons, Alexander, Eliza and their eldest son.

We’re almost there! Almost immediately after leaving Trinity Church we passed the Charging Bull or the Wall Street Bull. It was mobbed. And we were very tired. So we passed it right up.

All that is left is walking another block into Battery Park and heading a few steps further south so that you can see the Statue of Liberty, barely.

We made it, 5 hours and 40 minutes of walking 16.4 miles, tip to tip. By the time I got back home, it had been 7.5 hours, door to door for my top to bottom Manhattan walk.