How to take a country kid to the big city and have a great time

Hello from North Haven!

Bill, Penrose and I are back on island after a quick trip to New York City to visit my sister’s brand new baby! We’ve never been aunts, uncles or cousins before, and so far it’s a lot of cuddly fun.

The cuddliest fun.

Pen’s visited a lot of places – San Diego, Boston, Sedona, Philadelphia before she was very mobile – but New York seems like the apex of the city vacation. After all, the song says “If I can make it there, I’ll make it anywhere,” right?

Overall, the trip was fantastic. I’m not necessarily a calm traveler, but I noticed that I felt pretty relaxed the whole time. Penrose thinks sidewalks are a huge novelty in and of themselves, and found every nook and cranny and skyscraper noteworthy. Bill loves the chance to take city photos to contrast with his usual portraits and landscapes, and of course the food situation can’t be beat.

For those of you considering a city trip with your country kids, here are a few things that made it work well for us:

1. Be prepared. For us, this meant everything from carrying wipes and snacks in my purse to practicing safe street crossing with Pen before the trip. The island has no stop lights, crosswalks or sidewalks, and knowing about those things ahead of time helped her to know when to stop and when to go, and when to hurry.

2. Plan downtime. The city is full of brand new sights, smells and sounds for a country kid. Sirens go from rare to constant, neon abounds, and the crush of people can be overwhelming. Plan some time in the hotel, friend’s apartment or AirBnB where a nap or other relaxing activity happens (for us it was watching Magic School Bus Rides Again and holding the baby). Although Pen was a real trooper, we definitely noticed some sensory overload by the end of the trip.

3. Take the subway. We weren’t sure about what mode of transportation we would use – Lyft with a carseat? Bus? Subway? Walking? – and had to cross Manhattan to get from our sweet cat-sitting gig in the West Village to my sister. We walked the mile-and-a-half each way on the first day, which was a great chance for Penrose to explore. For fun on the second day we took the subway. It cut out a little bit of walking, although it was still about 3/4 mile total, but more importantly Penrose got to experience something totally new. Despite the unseasonably tropical temperature in the station, she thought the subway was pretty magical.

I don’t think I ever had this much fun on the subway in Boston.

4. Cities are for kids. Although the thought of traveling with a young country kid to the big city seems daunting, cities are full of young kids. They’re scootering down the sidewalks ahead of their parents, climbing on the playhouse at the park, and taking advantage of all the fun things a city has to offer. A visit to a museum or library is great, but balance it with unstructured play time in the surprising number of playgrounds and greenways. Penrose enjoyed the playground near my sister’s apartment, although city playground etiquette is a lot different than on island where she knows everyone and their parents and grandparents and dogs. We took the ferry to DUMBO, the Brooklyn neighborhood that’s home to Brooklyn Bridge Park and great views of the Statue of Liberty, where she rode a carousel, found yet another playground, and did some ice cream-fueled running around before falling asleep on the boat ride back.

5. Eat up. I love a good Broadway show or concert, but if I’m being honest, the real reason I love to visit cities is to eat. New York, of course, offers an overwhelming array of any type of food imaginable. Kids can be pretty adventurous eaters if given the opportunity, but they don’t have to be. For every Szechuan noodle with chili oil (which Bill and I ate; Pen had fried rice) there’s a Shake Shack, Papaya Dog, or pizza place. There are also interesting variations on familiar classics, like Pink Bear‘s Thai rolled ice cream, which was a big hit. Pack snacks too, though – I underestimated how much energy Penrose was burning through walking and just being in the city.

Helping a country kid feel comfortable in a city environment opens travel and education doors for their entire lives. Eating Szechuan and Indian food, riding the subway, observing members of the Orthodox Jewish community on the ferry, using crosswalks and public playgrounds are all experiences Penrose can’t have on island, and some are hard to find anywhere in state. I’m excited for more visits with my sister and her wonderful son, and more enriching experiences in cities around the world.

Just look at him. I mean really.

Courtney Naliboff

About Courtney Naliboff

In addition to this blog, I'm a contributing writer to, a Jewish parenting site, a blogger and book reviewer for, and the author of Salt Water Cure, a column in Working Waterfront. I report news from North Haven for Working Waterfront and Island Journal, and was a speaker at the Maine Conference for Jewish Life in 2015. Follow Frozen Chosen on facebook or visit my Web site for more writing and free music to download!