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What to do in New York City with a Five-Year-Old

Ashley Greer

As much as I love DC and Old Town Alexandria, there is nothing quite like a visit to New York City to delight and inspire all the senses. As a child I remember how special those times I got to visit New York were, and as a teenager was fortunate enough to spend one very impressionable summer attending fashion design classes at Parsons School of Design. Needless to say New York occupies a very special place in my heart.

Now that I am a parent, I want my child to grow up having a familiarity and comfort with this iconic destination.

Finn, who turned 5 this June, loves to travel and experience new cities. He has a generally easy going temperament and is adventurous. The only thing we really needed to be mindful of was loud noises, as he gets very upset and scared if anything is too loud or unexpected.

So, here is what we did for his first quick trip into the city.

1) Pick the right hotel. We stayed at well known hotel on the Upper East Side near Central Park. I chose this location because I was traveling alone with my son, and wanted somewhere that felt familiar, safe, close to the park, had valet, and room service. Surprisingly enough many hotels are not offering room service, so be sure to check first if this is something you enjoy. I did look at several midtown and downtown hotels, but ultimately, wanted to avoid the more frenetic feeling and congestion of those locations. Again, this had a lot to do with Finn’s particular sensitivity to noise, and I needed to be sure his first experience in New York felt safe to him.

2) Central Park Zoo. While it can’t really compare with most major zoo’s (DC, Bronx, San Diego), it was fun and a nice easy thing to do. There were lots of shaded walkways, and the sea lions and penguins were a big hit. Go ahead and watch the movies Penguins of Madagascar, or Madagascar to get your kiddo extra excited. The snow leopards were out preening and looking very majestic.

3) Heckscher Park at E 65th st., was the unexpected Finn favorite. While there were other things I would have wanted to do, I could tell Finn was really in the mood for some good playground play. After leaving the zoo, I googled “park near me” and this gem popped up. What I had not anticipated is that while it does have lots of regular playground equipment, the best part was what I like to call, the “Water City.” It is a splash park combined with little walkways and turrets that water runs through. Absolutely bring water shoes, bathing suit and a towel or you will end up like us . . . 1 kid sans shirt or shoes, and regular shorts soaked through. I’m pretty sure this actually ended up being Finn’s favorite part of the city.

4) Snow Cone or Ice cream from a truck. Simple enough, no explanation needed. Sit in the shade and take in everything around you.

5) Rickshaw ride. Finn thought zigging and zagging open air through the traffic was great fun, and asked if we could take a ride every time he saw one. WARNING!!!! Negotiate your price first. I made the mistake of not doing so and when our trip was over, the guy tried to charge me $77 for an 11 minute ride. Needless to say, I wasn't paying that, but it did make for an uncomfortable 30 seconds, before I handed him $25 and got out of there. SMH I totally knew better!

6) FAO Shwarz, but actually I would skip this the next time. This legendary toy store is really not what it once was, it feels crowded and is all about the build a bear/doll/car experience. I think if we weren’t still in the midst of a pandemic, I may have enjoyed this more, but really I just wanted to be in an out. The store has arrows for one way traffic and winds you throughout the crowded and narrow aisles. Finn was pleased with his “Make your own popsicles” selection.

7) New York Pizza. Yes, just about any large slice will do, and they can be found on the UES by googling “Pizza Near me” and following the walking directions on your phone. Of course you can sit at a lovely trattoria, but with a 5 year old its fun to have the “authentic” experience where they can just chill.

8) Times Square after dark. Another location that was not at all how I remembered it, wow! Finn and I ventured out at about 8:30 pm and found ourselves in the midst of day-glow twilight land. This was very much pushing the boundaries of his 5-year-old threshold, so after a quick look around and a couple of photos we headed out of the main square and grabbed some ice-cream on a quieter street. We then hailed a taxi and high-tailed it out of there. Even though we did’t spend more then 15 minuets there, that was plenty of time for him to have the experience, and it was a positive and utterly unique one.

9) Taxi Rides. Simple but fun for a kid who is so used to always being buckled into his booster seat. He also thoroughly enjoyed watching the adds and mini clips on the taxi tv. Something that felt new to me, were all of the taxis with big skylights built in so you could see the towering skyscrapers, a very nice addition. All of the taxi’s had full plastic of plexiglass screens to help prevent against the spread of germs, this is 2021 after all.

10) Lego Store. We went to the one in the Flatiron district because it is supposed to be bigger and have a better selection. It was a great store . . . nothing to write home about, but New York is a city for shopping, so it was fun to let Finn pick out some special items. He went with the Mario collection, apparently he has been watching Mario on YouTube Kids . . . .

11) Bubble Bath. No way around it, after being out in the summer city, your kid is going to need a bath, and bubble baths are fun! I let Finn fill up his tub all the way with lots of bubbles and just play until he was ready to get out.

12) Room Service. Now this does not have to be a New York thing, and a lot of people frown on room service, but I personally find it delightful to eat my dinner in PJs while watching an inroom movie. Plus, this was our compromise to eating in a restaurant. We have actually not sat down inside a restrung since February 2020, and even though we are traveling, I wasn’t quite ready to break the seal on this one.

13) Walk. A classic pastime for any city, just make sure to do this before you take any other mode of transportation. Once Finn had taken a cab and a rickshaw that was all he wanted to do . . . no more walking . . . and he was sure to tell me every 30 seconds.

14) Jump on the Bed! Classic hotel behavior for the kids under 10.

So, this was our quick Summer trip into New York City for my 5-year-old’s first taste of the Big Apple. Before we left, I polled my IG community for their top recommendations, and while we didn’t have time to experience them first hand, maybe they will be helpful for you!

Note: Some of these are currently closed or have ticketed openings. Please check first and reserve your space to avoid any disappointment.