We spent a long Labor Day weekend in New York City with our family, and it turned into one of those trips that felt completely full in the best possible way—packed days, a lot of variety, and a mix of iconic New York experiences we had all been wanting to check off for a while.
For my husband and me, the US Open was the anchor of the trip. We’ve been making our way through the tennis Grand Slams, and this was our first time at the tournament in New York. At the same time, we built the weekend around our kids’ summer birthdays, turning the trip into a series of “experience gifts.” Our son got tickets to a Mets game, our daughter went to an NYC FC match at Yankee Stadium, and together we managed to check off both NYC baseball stadiums in a single visit—something we’ve been intentionally working toward as we visit different parks.
We also added a day in the Hamptons, which ended up being one of the most unexpectedly memorable parts of the entire weekend.
Where we stayed (Chelsea)
We stayed in Chelsea, about a mile from Times Square. It was a very manageable walk for our kids, and it gave us a chance to see a bit more of the city on foot. If we were to do it again, staying closer to Times Square might have been a little more convenient, but overall the location worked well for us.
One thing worth noting: very few NYC hotels have pools. We assumed that might be a disappointment for the kids, but the reality was that we were so busy exploring that it never even came up.
Times Square & Rockefeller Center
This was our most classic “tourist” stop of the trip, and the kids loved it. We spent time walking through Times Square, browsing shops, and soaking in the energy of the area.
A highlight for them was the M&M Store, where they got to customize their own M&M’s. It was one of those simple-but-fun New York moments that stuck with them more than we expected.
Central Park (by e-scooter)
We took the subway up to Central Park and decided to rent e-scooters once we arrived. After a quick conversation with a rental booth attendant, we were pointed in the right direction and were on our way.
It wasn’t the cheapest activity, but it ended up being one of the best decisions of the trip. The park is large enough that we knew our kids wouldn’t want to walk it for long, and the scooters made it fun for everyone. We looped around the park, stopped near the fountain for a break, and realized afterward that an hour would have been plenty instead of an hour and a half.
World Trade Center & the Oculus
We visited the 9/11 Memorial, and we were genuinely surprised by how engaged the kids were. We expected a quick visit, but they spent time reading names and asking thoughtful questions, which turned it into a more meaningful stop than we anticipated.
Right next door, we explored the Oculus. While the shopping wasn’t a major draw, the architecture alone is worth seeing—it’s one of those spaces that feels striking the moment you walk in. We also stopped at the food hall there for lunch, which made it an easy and convenient break in the day.
US Open
Our evening session tickets began at 5:00 p.m., and we took the subway out to Queens. The ride was straightforward, but it does take closer to 45 minutes to an hour, so it’s something to plan for in advance.
The grounds were incredibly busy from start to finish. Lines for shops were long enough that we didn’t go inside any of them, and even grabbing food or drinks required patience. A friend who attended daytime sessions mentioned those felt much more relaxed, so that’s something we’d consider next time.
That said, the evening atmosphere was unforgettable. The energy in the stadium under the lights made it one of the standout experiences of the entire trip.
Mets Game
We took the subway out to Citi Field for a Mets game, and it turned out to be easier than expected. We had originally planned to Uber back, anticipating post-game crowds, but the subway line was efficient and not nearly as hectic as we thought.
The stadium itself was great, and the game had a fun, relaxed energy. It was a great addition to the baseball stadium “checklist” we’re slowly working through.
NYC FC at Yankee Stadium
Next up was a soccer match at Yankee Stadium. We took the subway there, which was simple and straightforward, and then opted for an Uber back to the hotel since it was late and we wanted a quicker return.
The ride back ended up being a nice bonus—we drove through Manhattan at night, which was beautiful in a completely different way than seeing it on foot.
As a venue, Yankee Stadium didn’t stand out as a favorite, though it’s worth noting we were there for soccer rather than baseball. Still, it felt like a worthwhile experience to do at least once.
The Hamptons (and Montauk)
Since we were already so close, we decided to add a final adventure: a day trip to the Hamptons.
We picked up a rental car at LaGuardia early in the morning and drove out, stopping through Westhampton, Southampton, and East Hampton along the way. Each town had its own charm—beautiful streets, upscale shops, and a very different pace from the city.
We stopped at the beach in one of the towns, where the kids swam while we relaxed, and even spotted a dolphin surprisingly close to shore, which became one of the unexpected highlights of the day.
From there, we continued on to Montauk, which felt a bit more rugged and laid-back. Walking out to the point and sitting by the rocks overlooking the water was incredibly peaceful. The downtown area was small, cute, and easy to explore.
Because it was Labor Day weekend, things were starting to wind down, but it made us curious to return when the area is in full summer swing. Montauk, especially, felt like somewhere we’d love to spend a few days rather than just passing through.
TBD Travel with April 