Living far from family has one inevitable by-product: our children grow up on road trips. From the time our boys were tiny, we’ve been packing the car and heading out for days at a time. Those long drives became part of our family rhythm—regular escapes filled with stopping points, songs, snacks and whatever kept the hours moving.
When the boys were little, our road-trip entertainment was a homemade affair. Long before portable DVD players were common, we rigged up an inverter, a garage-sale television and our home VCR so cartoons could play while we logged miles. It wasn’t glamorous, but it worked—and it bought us quiet stretches to drive and talk.
Now that the kids are older, our packing list hasn’t changed much: plenty of snacks and an entertainment setup tailored to the times. On this trip we even brought along a Wii (yes, really!). 
Last Tuesday we rose before sunrise to catch the first ferry off our little island. We were bound for Calgary, Alberta, for a very special reason: my in-laws are celebrating their 50th wedding anniversary this year. Although the official date isn’t here yet, the family had already started celebrating—some of them even took a cruise—and a few of us decided to join in with our own surprise.
The blue sky and sunshine on this trip were incredible. This single travel snapshot shows my husband (center) and our two sons who still live at home — we missed you, Brad!
The plan was simple but heartfelt: a special meal, carefully planned and cooked, made just for Mom and Dad—and kept secret. For weeks my husband and his siblings exchanged calls and coordinated details until everything was ready.
We arrived and waited in my brother and sister-in-law’s living room. Mom and Dad believed they were being taken out for supper. Instead, when they opened the door, they walked into a room full of family.
Surprise! The look on their faces was priceless. My mother-in-law later joked she thought she was seeing a vision. It was a rare surprise for me, too, and one of the most joyful family reunions I’ve been part of.
Happy, happy anniversary, Mom and Dad. It felt good to celebrate this milestone in a warm, intimate way—close family, shared memories and plenty of laughter.
We spent three delightful days together and then began the long drive home on Sunday: about 16 hours on the road. To stay awake and keep the car lively, my husband had recently bought a copy of Malcolm Gladwell’s Outliers. I started reading it aloud to him, mostly to help keep both of us alert. To my surprise, the back seat fell quiet: the kids had stopped whatever they were doing and were listening.
We ended up listening to and discussing more than half the book during that drive. Outliers sparked conversations about what success really means, how opportunity and practice shape achievement, and even how different professions and cultures influence outcomes—from athletes to engineers to small-business makers. Those discussions led to unexpected questions from the kids about definition of success and parenting approaches—thoughtful, engaging topics for a long car ride.
Once darkness fell, we turned off the reading for safety, but the memory of that shared learning stuck with us. Reading aloud together turned an otherwise monotonous drive into a meaningful family experience—an easy, inexpensive way to create connection and conversation on a long trip.
So what do you pack for family road-trip entertainment? For us it’s a mix of snacks, gadgets, and unexpected moments like a book that turns the miles into memory. And no judgment here if yours includes a TV and a Wii—whatever keeps everyone content and engaged is a win. 