Manhattan Tip-to-Tip Walk

One walk that I’ve been interested in trying for many years is the tip-to-tip walk in Manhattan – essentially walking from the northern to southern tip of that NY island. Going “straight down Broadway” the whole way is roughly 13 miles, though it’s common to zig-zag to various sites along the way. While it’s not a short walk, it is also quite doable in a day. And there’s an immense variety in things that you’ll see along the way.

Why do it? Manhattan is full of everything imaginable – I found it to be just a super interesting urban walk. And, even though I’ve been to New York a ton of times, I saw things on this walk that I’d just never gotten around to seeing, e.g. the Apollo Theater in Harlem, the Inwood Park and Cloisters area in Upper Manhattan, various historic brownsones/churches/cathedrals. And as a plus, along the way, you’re often not more than a block or two from a coffee shop or tasty snack.

Planning/Logistics

I’d learned of the tip-to-tip walk years ago after a father-son trip to New York, but filed the idea away for “later.” Most of my real planning was the week and the night before – I read some blog posts and got some AI summaries that indicated how to get to the starting point, which routes to take, how long it takes, and such. (You typically do the walk from North to South, and start by taking the subway to the 215th Street Station, walking the last few blocks)

It seemed reasonably do-able, the weather was good, and I had a window to go – so I decided to go. In my case, I live a 4 hour drive from NY in Boston, so I booked a midtown hotel and parking spot, and drove there the afternoon before the walk.

Clothing-wise, you mostly need comfortable shoes and appropriate layered clothing for the weather. For your phone, it’s a good idea to take a power bank. For your stomach, there’s a lot of food/drink to buy along the way.

Make sure that you’re able to do a longer walk. And if you like this walk, maybe consider a stretch of the Camino de Santiago in Spain in a future year!

(Just to note, this sort of walk is not necessarily appropriate for most on a first trip to New York – in that case, there are so many tourist highlights to see in NYC for which to save your steps – e.g. walk the Brooklyn Bridge, go to the Met, see a Broadway show, explore Central Park, go up the Empire State Building, see the Statue of Liberty… one can go on and on).

Route Summary

On the right is my route that Strava recorded. I determined mostly on the fly, though having read the AI notes the night before. The naive “straight down Broadway” is about 13 miles, while my route was somehow 22.5 miles (!) – so be careful with the zig-zag detours if you don’t want to walk too much. But in my case, I elongated the route because part of the goal was to leave the hotel at sunrise and reach Battery Park at sunset.

Here’s the short version to summarize the steps that I took, and then I’ll go through the route in detail:

After the Broadway bridge from the Bronx, I detoured to explore the Inwood Park and Cloisters area in the upper tip of Manhattan. Then I went down Broadway.
After the Washington Heights area (170th Street), I switched from Broadway over to St Nicholas Ave for a while, which had more historic buildings.
By 125th St (MLK Blvd), I explored the area in Harlem by the Apollo Theater.
By 116th St, I cut through Morningstar Park to the Columbia University area.
Alternated between Broadway and Amsterdam Ave through the Upper West Side. Had lunch around 72nd St.
After lunch, continued down Broadway to the bottom of Central Park, where I walked east to 5th Ave, to avoid Broadway through midtown.
Took 5th Ave through Madison Square Park, then followed Broadway to Union Square.
Took a longer detour along 14th to Greenwich Village, and eventually back to Washington Square Park.
Went to Little Italy (east along Houston St to Mulberry Street) and skirting Chinatown on Canal St.
Again, down Broadway, detoured to the Freedom Tower, and glimpse the City Hall and the Charging Bull.
Reached Battery Park 20 minutes before sunset!

To the Start of the Walk – to 220th Street / Inwood Park Area

Leaving my midtown hotel at 6:30am, I grabbed a quick breakfast nearby, and got on the #1 subway line to the 215th Street station – the train part is roughly 30 minutes from midtown. From that station, it’s another 5 blocks or so to the Broadway bridge between the Bronx and Manhattan. When all was said and done, I made it to this tip around 7:30am.

Note that this section of at the upper tip of Manhattan isn’t the most photogenic. It was full of everyday life – commuters, construction workers, and people taking their kids to school. I did cross the Broadway bridge to the Bronx and back to feel like I hit the “boundary” of Manhattan.

From there, I also wandered around nearby Inwood Park, at the northwest tip of the island (the Broadway bridge is effectively the northeastern tip). It was fairly scenic, much nicer than the Broadway bridge area, and I would have spent more time there, but I realized that I should pace myself.

Upper Manhattan, North of Central Park

From Inwood Park, I made my way down Broadway, making a pit stop at the northern-most Dunkin in Manhattan. And several other pit stops that I’ll skip.

Within the next many blocks, I ran into some interesting tidbits – a “cross” that was left in the aftermath of the 9/11 wreckage (moved to the grounds of the Church of The Good Shepherd), the Dyckman Farmhouse Museum (built 1764), and the Cloisters Museum (part of the Met collection). The Cloisters is up a path in Fort Tryon Park (roughly 200th St), and had nice views of the Hudson.

From there, I wandered down Broadway, which was some mix of apartment buildings, bodega shops, and stands on the sidewalk. Around the George Washington Bridge (179th Street), it started getting busier.

Turn at Washington Heights: Around 170th Street and the Washington Heights neighborhood, I went down St Nicholas Ave, per the AI suggestion – because it had more historic brownstones and churches.

Harlem: Soon enough, I was in Harlem (around 125th Street or MLK Blvd), where I walked by the famous Apollo theater. In that area, many of the streets are named for famous African Americans like MLK, Malcom X, and Fredrick Douglas.

Columbia University: I’d never been by the Columbia University area around 116th Street, so walked west that direction. As of 2026, it is closed to the general public (presumably because of the large 2025 protests). One thing that struck me was that while it’s near Harlem, it feels very separate because the geography is somewhat uphill from Harlem – walking through Morningside Park, you go up many stairs. Below is the of Harlem from Morningside Park, as well the entrance gate to Columbia.

Just a couple blocks away on 112th Street was the St John the Divine Cathedral, which was well worth a photo on the outside.

Upper West Side and Midtown

One route suggestion was to go through Central Park, but having spent my share of time there, I was more interested in continuing around Broadway in the Upper West Side. I had reached 110th Street, or the northern limit of Central Park, by about 11am. Having been walking from 220th street since 7:30am (and leaving my hotel at 6:30am), I started thinking through my route for the rest of the day. My goal was lunch and a break around noon, and finishing at Battery Park around 4:30pm (sunset that November day was roughly 4:50pm).

Upper West Side: Through the Upper West Side, I alternated between Broadway and parallel Amsterdam Ave. I think Amsterdam Ave may have had more restaurants on it, but it may have just been the blocks that I was on.

Lunch: I had lunch at a sushi place by 72th Street, around noon. I imagine that sushi sounds light fare for a long walk, but given the numerous stops for treats that I’d had earlier in the morning, it worked. One related photo, a scene repeated all over NY, is of a queue of folks waiting at a shop for niche food (Hungarian pastries in this case).

Lincoln Center/Park: After resting at lunch, I continued down Broadway through the Upper West Side to the Juliard/Lincoln Center area, which coincides with the southern tip of Central Park at 60th Street. I decided that I’d prefer not to take Broadway through Times Square mid-day (personal preference), so I elected to walk along 60th Street to 5th Ave, and traverse midtown via 5th Ave.

Midtown: Going down 5th Ave, with all its stores, felt somewhat more familiar. I walked by Rockefeller Center (the lego store version of itself at Rockefeller Center pictured), St Patrick’s Cathedral, and the Empire State Building (34th St). There are many more pictures that could be posted in this area, as they are the prime tourist area.

Madison Square Park/Union Square Park: Broadway intersects 5th Avenue around Madison Square Park, so I started following Broadway again at that point, walking through both parks. There are always a number of interesting stands and exhibits and people in those parks.

Lower Manhattan

Greenwich Village/Washington Square Park: At that point, I decided to detour quite a bit west to Greenwich Village – taking a beeline down 14th Street. This was admittedly somewhat out of the way, but I was running ahead of schedule, and decided to spend a bit of time there. Plus, I enjoy stopping at the neighboring Washington Square Park and NYU area.

After resting a little in Washington Square Park (note: parks like these have restrooms), I continued on to Little Italy. At the end of Little Italy, bordering Chinatown, on Canal Street, there always people hawking fake watches and handbags. There seemed to be more of such vendors out than a few years back.

At that point, it felt a lot more like Lower Manhattan. I walked by City Hall, and did a short detour to see the Freedom Tower and the WTC Memorial.

Nearing the end, I walked by the famous Charging Bull of Wall Street, and turned around to see the Lower Manhattan Skyline.

I did make it to Battery Park roughly 20-30 minutes before sunset, and was able to sit in one of the benches and watch the sun set by the Statute of Library. A great ending for a great walk!

After the sun set, the express train on the subway got back to midtown quicker than I expected. I was ready to rest some! For dinner, I picked up a gyro sandwich from one of the halal carts on way back. Though after resting in my hotel room, I did take a walk around Times Square – and got some ice cream – before turning down.

Some Take-aways

The Manhattan tip-to-tip walk was really enjoyable! I definitely recommend if it you like walking and have seem many of the “highlights” of New York, but want to see more.

Fall and Spring are great – I’m glad that I did it in the Fall when it was pleasantly cool but not cold.
Bring layers of clothing and good shoes. Bringing snacks/water is less important, since there is food/drink for sale everywhere.
Bring extra power for your phone. I used my phone’s battery and most of the powerbank’s battery, even with low battery mode on.
It’s easy for detours to add steps. If you’re more comfortable with 13-16 miles, avoid the wild detours that I did, since I clocked in a 22.5 miles. But if I’d omitted the Inwood Park/Fort Tryon and Greenwich Village, it would have been more managable.
The North-to-South direction is the right choice, things largely get more interesting over the course of the day.