Lessons from the Road
What I learned from 13 days Clark Griswold-ing the Northeast
👋Hello my friend — It’s been a couple weeks since I’ve been in your inbox. The reason? I was off on an epic two-week Northeast U.S. road trip with my family. We’re back now—school has started, and the trip is already feeling like a distant memory. But before all the details get lost to history, I thought I’d share some of the lessons I learned along the way. Stick around til the end for some epic content recommendations, including one I implore you to consume.
Let’s do it.
Why this trip?
For years, I’ve wanted to take my kids on a “proper” trip up north. I grew up in Connecticut, lived in Boston and New York, and spent many summers on Cape Cod. But my kids have grown up in North Carolina. A different world.
I wanted them to get a real feel for the Northeast—not just passing through, but really being in the places that shaped me. I wanted them to know the hot dog stand where I ate as a kid, the townhouse I lived in at college, the ballpark that shaped my fandom, the city streets I once called home.
Life, work, and COVID pushed it back, but this summer the stars aligned. We loaded up the SUV (Griswold-style, roof carrier and all) and hit the road.
Stop #1: Hershey, PA
Confession: I don’t like theme parks. My kids love them.
So we started at Hersheypark. Roller coasters, chocolate, ice cream, and my first root beer float in about 25 years. The kids were in heaven. I was…fine.
Lesson: Sometimes discipline (like my diet) needs to take a back seat to joy. And when you’re on the road, perfection isn’t the goal. Flexibility is.
I did try to sneak in some beef jerky and protein bars along the way, but Hershey was a reminder: if you start a trip with three kids by laying down too many rules, you’re setting yourself up for failure.
Stop #2: The Poconos
Camelback Resort, big waterpark, ski condo, ziplining, tubing—the whole thing.
My wife initially questioned this choice. (The Poconos aren’t exactly seen as “peak luxury” these days.) But luxury wasn’t the goal. Entertaining kids was. And they loved it. My five-year-old was grinning ear to ear as we went down waterslides together. My 11 and 14-year-olds zoomed off on the zip line. Even I had fun in ways I didn’t expect.
Lesson: As parents, sometimes you take one for the team. And often, you discover that what delights your kids ends up delighting you, too
Pitstops in Connecticut & Massachusetts
We hit Blackie’s in Cheshire—an institution that hasn’t changed much in 100 years. Burgers and hot dogs, old-school prices, the same blue-collar crowd I remember from growing up. And still, much to our chagrin, no dancing allowed.
We swung by my childhood home, too. The yard was overgrown, the neighborhood a little worn down. But stopping and taking a quick look at that place, pointing out where I played wiffle ball with friends, gave my kids a picture to hold onto.
We also made a quick detour through my alma mater, Stonehill College in Massachusetts. I walked them past my old townhouse (in need of a paint job!), the cafeteria, the spots where I spent four years. To me, it felt like a time warp. To them, it was cool to connect the dots: “So this is the place Dad went to college back in the 1900’s.”
Lesson: Show your kids your roots. Even if it’s just five minutes in the driveway or a quick campus walk, it helps them see you more fully.
Stop #3: Boston
Boston was special. We rented an Airbnb right on Beacon Street—brownstone charm with modern updates. Two bedrooms, a kitchen, laundry (a lifesaver on a 13-night trip). Pro tip: If you’re a family of five, skip the hotels and opt for Airbnb’s.
First night, we hustled to Fenway Park. My oldest son—massive Red Sox fan—was practically levitating. I loved watching the game, but even more, I loved watching him watch the game.
An old friend, Dave, surprised me by grabbing tickets and joining us with his son. That kind of unexpected reconnection is gold.
The next day: duck boat tour, wandering the Seaport, stumbling into a high-end mini-golf place. In the afternoon, the kids hit a wall. Instead of pushing through, we hopped on the T back to the Airbnb, rested, then recharged for a big Italian dinner in the North End. Along the way, we got pulled into a street performer’s act at Quincy Market.
Lesson(s):
Reconnect with old friends whenever you can. You’ll never regret it.
Don’t overschedule—some of the best discoveries (like mini-golf or street performers) happen when you leave space for them.
And yes, the T was incredibly easy. A quick tap of the phone and you’re through the gate—no more paper tickets or Metrocards. Kids ride free, which we discovered after a day of overcomplicating things.
Stop #4: Cape Cod
This was the family centerpiece. We stayed in an Airbnb with my mom, her fiancé, my brother, and his family. Hit the beach. Rented bikes. Ice cream shops and mini-golf. A stop at the Beachcomber in Wellfleet and Arnold’s in Eastham.
It was classic Cape Cod—waves, sand, and lobster rolls. And more importantly, time with family. Board games. Beach chats. Just being together.
We even hit Raising Cane’s near Providence on our way out — because apparently 14-year-olds are obsessed with that place.
Lesson: Make the time for family. As kids get older, nieces move into careers, and everyone’s schedules fill up, it’s harder and harder to gather. But it’s worth the effort.
Stop #5: New York City
Last major stop. We rolled in Griswold-style, roof carrier on top, and I promptly spent an hour and a half trying to find parking. Garage after garage turned us away until we finally stashed the carrier inside the SUV and found a spot through an app.
Once settled, it was everything I hoped: Upper West Side hotel, a walk in Central Park (and by my old brownstone on 73rd street… even though I couldn’t remember which one it was)… dinner at a Mexican spot around the corner, wandering the city I once called home.
The next day, the kids loved Bryant Park ping-pong—probably more than the Statue of Liberty they barely looked up at on our boat tour. And that’s OK. Kids show you what matters to them if you’re willing to pivot.
We also discovered the Spy Museum, which turned into a highlight. Family challenges, mental and physical games—it was the kind of activity where everyone gets into it. Dinner that night in the Village ended with milkshakes the size of my kids’ heads.
Lesson(s):
Use the subway. Tap your phone and you’re in. Kids ride free. We whipped around the city with ease. Only one cab ride.
Don’t try to force your kids to care about the “big” sites. If they’re more into ping-pong in Bryant Park, roll with it.
Go where curiosity leads—you might stumble into the best parts of the trip.
The drive home
After lunch with friends in New Jersey, we had planned to stop in D.C. for a night. But we were cooked. We bailed, turned the car south, and made a run for home.
We tried to power through to Charlotte in one day, but ten hours in, we surrendered in Roanoke, VA. A cheap hotel, a quick breakfast, and we were back on the road.
Lesson: Sometimes the best decision is to call it. A day of rest before school started was worth more than another stop on the itinerary.
Big Takeaways
Looking back, here are the big lessons that will stick with me:
Take the trips. Don’t wait for the perfect time. The window where kids are this age is small.
Roots matter. Show your kids where you came from.
Unstructured time is a gift. Some of our best moments came from wandering without a plan.
Screens aren’t everything. We had to enforce breaks so they didn’t miss the world flying by.
Time > perfection. There were fights and frustrations, sure. But the point was time together.
I’m grateful we made it happen. Road Trip 2026 is already in the works (Europe? Out West? Alaska?). We’ll see.
Content Diet
A couple things I’ve been listening to lately (don’t miss the last one):
Tim Ferriss x Kevin Rose — These guys hit a ton of topics in the latest edition of their aptly named “random show” but the one that stood out to me was their discussion about intermittent fasting. I’m a few days into IF myself… may be correlated with the number of desserts I’ve consumed recently as referenced above… and I found some helpful tips in this episode. Let me know if you’ve done intermittent fasting and have any thoughts on it. Also, big section in here on quitting alcohol, which is always interesting to me. I’m about to dial it way back after re-introducing it recently.
Tim Ferriss x Dr Jeffrey Goldberg. This was a super interesting conversation on all things related to eye health — including substantial discussions on losing our close-up vision as we age (and what we can do about it). I’m continuing to battle dry eye (and looking for solutions, literally and figuratively) so I’m all-in on anything that gets me smarter about my eyes.
Jeremy Stern’s epic profile of Joe Liemandt, Mackenzie Price, and Alpha School
It’s not often that I implore you to consume a piece of content. But I’m doing so today. This piece tells the story of the founders of Alpha School, a cutting-edge Austin, Texas-based school where, through the use of technology, students are achieving almost unbelievable outcomes. And, they’re doing it in just 2 hours per day.
My friends, education is about to change. We’re about to leave the “industrial age” aka teaching to the average (or the lowest common denominator), and enter the personalized age, where AI helps us understand each student’s strengths, weaknesses, level of understanding, areas of interest, etc.
This piece tells the story of a company at the leading edge of this revolution by tracing the lifelong journeys of the founders who are leading the charge. Well done to Jeremy Stern, Patrick O’Shaughnessy, my friend Matt Reustle, and the whole team at Colossus who continue to inspire on a regular basis with the quality standards they are setting when it comes to all things content.
If it’s not sacrilege to recommend listening to (rather than reading) such a beautiful piece of work, do this:
• open this link on your Google app
• on the top right-hand menu, choose “Read Aloud”
• 1.5 hours later, you’ll be sharing it with friends like I am now
Thanks, as always, for reading. By the way, if I missed you on this last trip, I’ll be in NYC and Boston for work this Fall, so let’s get a coffee on the calendar.
Until next week,
Greg