We had an amazing trip through New England with the family, and this is where the story begins. We’d always wanted to explore this corner of the country. Everyone raves about the cute small towns and the walkable cities, so we finally booked a trip covering Massachusetts, Connecticut, Maine, Rhode Island, and New Hampshire. Buckle up, because there’s a lot of ground (and a lot of miles on foot) ahead.

The Red-Eye Decision We Immediately Regretted

We booked a red-eye to Boston. At the time, this felt like a genius move: skip a travel day, arrive fresh at dawn, maximize vacation. But as the trip crept closer, reality set in, and we realized we’d essentially signed ourselves up to start our vacation completely exhausted.

We committed anyway, because that’s who we are. The adventure kicked off with a pleasant visit to the Chase lounge and a blissfully uneventful flight where Ariela slept through most of it, which was honestly the entire goal. Mission accomplished.

But you know how you can technically sleep on a plane and yet not actually rest a single cell in your body? That, combined with jet lag, hit us the second we landed. We took a taxi to the hotel praying for an early check-in, but they were sold out. The front desk kindly held our bags while we set off to explore Cambridge on fumes and sheer willpower.

Cambridge: The Highest Nerd Density on Earth

Cambridge is home to both Harvard and MIT, sitting remarkably close to each other. I’m fairly confident this neighborhood has the highest concentration of geniuses per square mile anywhere on the planet. You can practically feel your IQ rising as you walk around, or maybe that was just the jet lag talking.

We wanted an easy morning, so we ambled toward the university and stumbled onto a lovely breakfast spot called Tatte Bakery and Café. We shared an incredible shakshuka and I had one of the best pistachio lattes of my life. Genuinely a top-tier café. If you’re in the area, go.

A quick bit of history while we digest: Harvard was founded in 1636, making it the oldest institution of higher education in the United States. It predates the country it’s in by 140 years. It was originally called “New College” and was created to train clergy, before being renamed in 1639 for its first major benefactor, John Harvard, a name that will become very relevant, and very funny, in a moment.

Looking at Buildings We Weren’t Allowed Into

Fueled by breakfast, we set out to explore the main campus buildings. Here’s the catch: because Harvard is so famous and so swarmed by tourists, most buildings are closed to the public. Unless you’re on an official Harvard tour, you can’t really get inside. A few, like the main library, let you photograph the lobby, and we caught a peek into others as students badged in.

Even from the outside, the history and architecture are stunning. Redbrick Georgian halls, ivy doing its ivy thing, and centuries of overachievers echoing through the Yard.

The Statue of Three Lies (and the Shoe You Should Not Touch)

The main tourist magnet here is the John Harvard statue, and it comes with one of the best trivia stories in all of Cambridge. It’s affectionately known as the “Statue of Three Lies,” because the inscription reading “John Harvard, Founder, 1638” is wrong on all three counts:

1. It’s not John Harvard. No portraits of him exist, so the sculptor used a random student as the model in 1884.
2. He wasn’t the founder. He was the college’s first major donor (he gave his library and half his estate), but the school existed before he got involved.
3. The year is wrong. Harvard was founded in 1636, not 1638.

Three lies, one statue. Beautiful.

Now, tradition says that rubbing the statue’s left shoe brings good luck, which is why it’s polished to a golden gleam by millions of hopeful hands. What most of those hopeful tourists don’t know, but we did, is that Harvard students have a long-standing tradition of urinating on that very shoe as a prank, precisely because they know everyone will be touching it. It’s a beautifully cynical piece of campus folklore.

And yet. Eitan touched it anyway. Because wishes are expensive these days and you simply cannot pass up free luck, even the faintly biohazardous kind. Hand sanitizer was applied immediately afterward, for the record. Sarah, of course, being the wisest of us all, didnt touch it.

Harvard Square, Greek Snacks, and Kid Fuel

We wandered on to Harvard Square, a cluster of streets lined with shops and cafés. It’s pleasant but honestly not a must-see unless you’re in the mood to shop.

And you can walk by many on-going university tours and learn a thing or 2.

We stopped at a Greek café for lunch and, more importantly, an incredible pistachio Greek frozen yogurt. It was so good, and it instantly transformed Ariela from a wilting jet-lagged toddler back into a fully operational human. Never underestimate the restorative power of frozen yogurt.

MIT: Same Genius, Different Vibe

We walked a couple of miles south to the MIT campus, which has a completely different feel. The architecture is more modern, anchored by a very cool central domed building (that’s the Great Dome atop Building 10, a campus icon).

Ariela celebrated our arrival by sprinting across the grass for a solid while. Seriously, what is the deep spiritual connection between small children and open lawns? Scientists at MIT should really look into it.

Somewhere around the third courtyard, Eitan began quietly informing everyone that, honestly, he probably would have gotten into Harvard or MIT if he’d applied. This conviction only grew stronger with each building we passed. By the end he was fairly certain he’d have been valedictorian, captain of the rowing team with his skinny, scrunny arms, and possibly had a hall named after him. The acceptance rate here is under 4%, but sure, honey. We let him have it. Wishes, as we’re about to see, are expensive.

Crossing the Charles and the Houdini Plaque

MIT sits right along the Charles River, so we crossed the Harvard Bridge (confusingly located at MIT, not Harvard) toward downtown. This bridge holds a fun secret: a plaque commemorating a Harry Houdini stunt performed right here, where the legendary escape artist leapt into the river below, handcuffed, and freed himself underwater. Casual.

The bridge is also famous for being measured in “Smoots,” a unit based on a 1958 fraternity prank where students used a pledge named Oliver Smoot to measure the bridge by repeatedly laying his body down end to end. The bridge is 364.4 Smoots “plus one ear.” The markings are still painted on it today. Only at MIT..

Walking Boston, Because Boston Is Made for Walking

We quickly realized Boston is an incredibly walkable city. It has a fantastic public transit network (the “T” is the oldest subway system in America, opened in 1897), but walking felt like the better way to soak it all in.

We wandered through Back Bay, a gorgeous neighborhood packed with restaurants, shops, tourists, and locals alike.

Fun fact: Back Bay was literally an actual bay until the 1850s, when the city spent decades filling it in with gravel to create new land. So this elegant neighborhood of Victorian brownstones is entirely built on reclaimed water.

There were cool sculptures scattered throughout, and the whole area buzzed with energy.

Sunset on the Esplanade

We made our way to the Charles River Esplanade, the go-to gathering spot where seemingly all of Boston shows up at sunset to picnic, hang out with friends, and enjoy the golden hour.

There was even a pop-up beer garden. We watched the sun go down over the water, thoroughly charmed.

Then we started the walk back across the Longfellow Bridge toward our hotel, and the views were absolutely stunning. The bridge’s distinctive towers have earned it the local nickname “the Salt-and-Pepper Bridge,” which is exactly what they look like.

And yes, last minute we got the staller specifically thinking about today, so Arielita can sleep while we walk around in the city like maniacs. We promised this is the last trip with it!

Eleven Miles and Zero Regrets (Almost)

Boston feels genuinely safe, so we had no hesitation strolling around after dark. Some of the buildings are just spectacular at night, and walking past the MIT science labs was a treat, since many have exhibits right in their lobbies that you can enjoy from the street.

All in all, on a day when we were completely jet-lagged and running on airplane non-sleep, we walked 11 miles. Eleven! On day one! I sometimes feel a little bad for Ariela that she got saddled with such certifiably insane traveler parents. But then I remember she’ll have stories like these, a well-developed sense of adventure, and a slightly-too-early understanding of why you should never touch statue shoes. Worth it.

Bonus pic of the day: Boston has red fire alarm pull boxes on street corners because it is home to the world’s oldest municipal electrical fire alarm telegraph system, first installed in 1852. When pulled, these independent boxes send a precise, coded telegraph signal straight to fire headquarters to dispatch help instantly.