An Overnight Getaway Cured Our Back-to-School Blues

As a mom, there are certain milestones in your child’s life that you’re more prepared for than others. This year, my 4-year-old son Oliver hit a milestone that I was not prepared for at all: Pre-K. I knew that the school application process would be tough (it’s a hot topic in mom’s groups all over New York City), however, I never anticipated the rough time we’ve have once school started. Thanks to the big new school, the unfamiliar faces, and long school days, there were lots of tears from him (and me), which inevitably led me to question whether I chose the right school, and whether he’s too young to be there.


Of course, I’ll just have to wait and see how he adjusts before I make any more decisions about school. But, in the short term, I decided that we needed a little break — some sort of getaway for just the two of us. So, one Friday after school, we left our Brooklyn neighborhood and took the subway to Times Square in Manhattan for an overnight. With its bright lights, mega stores, and visitors from all over the world, Times Square is dramatically different from where we live, even if it’s only a short subway ride away. What better place to go for an adventure close to home? Since hotels are a huge novelty to Oliver, The Comfort Inn Times Square, where we stayed, only added more excitement to our adventure. And here’s the thing: We had such a wonderful time that I’ve decided an overnight getaway will become our new back-to-school tradition.

Here are 6 ways that we bonded, let loose, and reconnected during our getaway.

We ate dinner in bed. Oliver is never allowed to eat in bed at home, but I was more than willing to break this rule on our overnight. It was a special treat — and, let’s face it, I didn’t have to worry about crumbs in the bed. Oliver had a field day!


We had plenty of time to talk — really talk. Sure, we were in the same room the whole time — but, more importantly, being away from all the distractions of home inspired Oliver to want to talk. I decided not to grill him about his day at school (shocker: little kids don’t like talking on demand), and I found out more than I normally do! He talked about his teachers, his classmates, and more. Note to self: Back off at home, too!

We ditched our typical bedtime routine. One of the hardest things about starting the school year was enforcing a serious bedtime schedule and saying so-long to our chill summer routine. So, of course, staying up late enough to watch all of the lights in Times Square go on was a big part of what made this experience so fun. My son knows the order of our home bedtime routine at this point — dinner, wash-up, books, and bed — so to be able to shake things up and let schedules go, even for just an evening, was a thrill for both of us. There were no restraints, no “get to bed” a thousand times over, just a simple flow to the evening.


We enjoyed a movie in bed together. While Oliver is almost old enough to sit through a whole movie, somehow I am not (at home at least). There’s so much to do! But, in a hotel, there was no need to multi-task and do chores while “watching” a movie. Instead, we snuggled and giggled together during a lighthearted hour of Thomas and Friends Rescue on the Rails. What fun!

We discovered new breakfast foods. Oliver loves food and is very open to trying new foods, so the breakfast provided for us at the hotel was a fun little adventure in itself. Of course, he scarfed down the mini muffins and croissants first, but he also enjoyed fresh fruit and fell in love with maple-brown sugar oatmeal (something new!). The bottomless coffee was a big bonus for me.


We got to know a new ‘hood. Like most New Yorkers, we take Times Square for granted and leave it for the tourists. Meanwhile, it’s like Disneyland for kids! I can’t even count the number of times my son ooh’d and aah’d at what he saw. On our way to the hotel, we stopped and got a pretzel from one of the street carts. Then, Oliver ran into a souvenir shop to inspect the toy fire trucks, police cars, and souvenir cups. He was so excited it was as if we were in a different city. When we got to The Comfort Inn Times Square and he found out we weren’t following our nighttime schedule? Mind blown! We ended our adventure at a giant toy store with a Ferris wheel inside. Seems like Times Square is pretty cool, after all. 


It’s only been a couple of weeks since our getaway, but we’re already looking forward to our next mom-son overnight. I wonder which neighborhood we’ll explore next time? As our adventure proved, there’s plenty to enjoy close to home!

*This post is sponsored by Choice Hotels. Accommodations were provided. Thoughts and opinions are my own.