From Midtown to the West Village: A Walk Through New York City

New York City is not a place you simply see—it is a city you experience in moments. On a recent trip we started our first day near Times Square with tickets to the Empire State Building and a lunch reservation waiting for us in the West Village. But somewhere between those two plans, the day opened up. We made our way downtown on foot, and what followed was less about sticking to an itinerary and more about noticing how the city changed along the way. This is the first of 3 posts in a Spring trip to NYC, that we hope adds some inspiration to your next trip to the Big Apple.

Herald Square to The Empire State Building

We landed very late on a Thursday night so we were able to experience 3 full days in Manhattan. Despite the lack of sleep, we were ready to go bright and early. We headed out from our hotel in Times Square, walking from 42nd to 34th Street. The first thing we noticed was spring was in full bloom everywhere. We came upon Herald Sq but it was too early for a visit to the iconic Macy’s store, so we took a moment to enjoy the flowers.

From Herald Square we made our way to the first stop of the day; The Empire State Building. Despite dozens of trips to NYC, this was our first visit to the iconic building. Pro Tip: Plan ahead. Timed tickets are still used, and it expedites the entry process. We did see people buying tickets for later in the day.

So much history here! We learned that the building of the Empire State was the ultimate teamwork, as it was completed in just 13 months from start to finish. And, in 1930, it was the beginning of the depression, giving jobs to hundreds of workers.

Did you know that the workers truly worked in teams. If one person was out, the whole team didn’t work that day. And, the riveting job, was arguably the most challenging. One person, heated the rivet, then the next guy literally tossed it up 60 feet for the final guy to put it into place. Take time to read and view some of the history of this great building. It’s really interesting.

King Kong Photo Op

Of course, take time to get all the cheesy photos too!

There are two observation decks. The first (and most popular) is on the 86th floor. Once inside the elevator, in a quick minute you are at 86, where there are both indoor and outdoor observation decks.

Our visit was a bit of a hazy day but we were glad it was mostly clear! If you look closely you can almost see the Statue of Liberty out in the harbor.

Pro TIP: buy the ticket that also takes you to the 102nd floor. It does not cost that much more, and the day were there, we just about had the whole floor to ourselves!

Back down to 86 and then the elevator to the bottom. Overall, plan around 90 minutes to catch everything to see at the Empire State Building. And for $35USD also consider purchasing the fun digital picture package.

Madison Park to West Village

Our next stop was a bit of a downshift from the energy of Times Square and Empire State. We wandered towards West Village. This stretch is where New York begins to soften—the buildings get lower, the streets less predictable, and the pace just a little slower. After passing by the famous Flatiron Building, we came across Madison Square Park, where, even on a weekday, people were out enjoying the sunshine.

The light pole banners told us we were heading in the right direction but we came across what we thought was a church and it turns out it was the Jefferson Market Library and Gardens. We did not step inside but it was charming to see along the way.

After about a 35 minute walk we found ourselves at our lunch destination a highly recommended local cafe called The Little Owl. But we could not figure out why there were groups taking pictures outside.

After lunch, looking at the building more closely… it dawned on us! This building is Monica and Rachel’s apartment building from the 90’s television show, “Friends”(and Joey and Chandler’s). Here we were, right in the building an iconic TV show. The food was fantastic and the service great, in a perfect stop for lunch but soon we were out and about again.

Our next stop in this adorable part of West Village was to see the exterior of another iconic TV show; Carrie Bradshaw’s apartment from “Sex and the City.”

We then found the heart of the shopping in West Village, with both local and small chain stores. We could have stayed all day but it was time for the next adventure.

West Village to The Hudson River

After spending time wandering through the West Village, we realized we were not far from the Hudson River. Since it was one of those perfect spring days in New York, we decided to keep walking with no real agenda. That is often when the best parts of a trip happen.

Enjoy the Sunshine!

We found ourselves in Hudson River Park, following the walking and bike path along the water. It felt like a completely different side of the city—less rushed, more local, and full of people (and geese!) out enjoying the sunshine.

Before long, we spotted something unusual stretching out over the river—Little Island. Built on the remains of an old pier and opened in 2021, Little Island is a public park designed to look like it is floating above the Hudson, supported by its signature tulip-shaped concrete pillars. It feels both modern and whimsical, and somehow still peaceful in the middle of Manhattan.

We walked out onto Little Island and found gardens full of spring blooms, winding paths, and one of the best surprise views of the day.

There is also a beautiful amphitheater tucked into the landscape, with the New York skyline as its backdrop

From the edge of the park, we looked back toward Lower Manhattan and could clearly see One World Trade Center rising above the skyline. What a fantastic find for us, in our afternoon of wandering.

Take the Time

As we finally made our way back uptown, we stopped for fresh oysters and a glass of wine—one of those simple travel moments that somehow becomes the one you remember most. But we were tired, and, soon, made our way back to the hotel before the evening activities.

Back to Times Square

By that night, standing back in the lights of Times Square, it felt like the perfect ending to our first day. We had started with iconic New York and ended with the quieter side of the city—the neighborhoods, the waterfront, and the unexpected moments in between.