Casey Smith doesn’t always want his family trips to be comfortable.
“I recently read something about how there are three kinds of fun,” said the lawyer, Calgary native and father of four boys, ages 14, 11, 9 and 6. There are the times when everything is sunny and smooth, the times when things go wrong and you’re maybe even suffering a little—which often feels more fun in retrospect—and the times when…well, things aren’t fun at all.
“It’s the type 2 experience that enters our family psyche and becomes really memorable,” Casey said.
The family has plenty of opportunities for challenging fun on their travels, which often involve the outdoors. Casey and his wife, Julie, started hiking with their boys when they were babies, have explored National Parks in the U.S. and Canada, and recently completed a 17-kilometer family trek in Alberta, the Galatea Lakes Hike.
When their youngest son was a toddler, the Smiths went hiking in southern Utah. “He was walking on his own, and tripped and fell and started crying,” Casey said. “It turned out he wasn’t hurt or anything—he was disappointed. He said, ‘I thought I was a good hiker!!!’”
Feeling inspired? Casey shared his favorite app for planning hikes, advice for getting little ones going, and some of his secret spots in Canada.
One of the reasons we gravitate towards outdoor stuff is…
my philosophy is that you kind of have to push kids hard and give them that sense of accomplishment for doing hard things. Life’s not easy, but if you’re determined and put your mind to it, you’ll get through challenges. Nothing’s worthwhile without putting in some effort. I believe that kids are capable of a lot more than we maybe give them credit for. I mean, on most of the hikes we’re pushing them, but the next day we’re the ones who are sore and they’re just bouncing up and ready to go again.

Some of our favorite destinations are…
Banff and Lake Louise—which gets so flooded with tourists in the summer that we try to avoid it, and instead hit it in shoulder season. Waterton Lakes National Park is kind of our little secret corner of the province, but it’s getting more popular. We’re still planning before everyone grows up to do Disneyland again. And we loved Hawaii and have always wanted to go back. Last time we went to Oahu, but I think we want to go to the Big Island to be a little more off the beaten path and explore the volcanoes.
You don’t want to be in a windstorm or something and have things break or leak.
We motivate our youngest son by…
telling him there’s no other, say, three year olds or four year olds who can do this. If you start the day by telling them, this is going to be a real challenge, do you think you can do it? He’s like, “Yeah, I’m going to do it, nobody else can do it who’s my age.”
As important as family holidays and adventure are to us…
Julie and I find it really important to take some time for ourselves—even just a night or a weekend without the kids. It gives us a chance to recharge and keep our connection strong so we can be on the same team when we have full family activities!
I’m very much a…
planner, which my wife appreciates. We have itineraries drawn up to the hour. And we build in the chill time so they can relax. I’ll do the research and I’ll make a spreadsheet with the times. We try to give the kids some choice too, and it’s always good to have a plan B too, whether it’s for weather or people are tired and they don’t feel like doing a big thing. Even for hikes, I’ll have a couple of options.

My main trip planning tool is…
Google. For hiking and stuff I’ll use AllTrails—it’s good because it’s got everything and it’s got reviews from people who have done trails recently, so you know the conditions. And when we went to Disneyland, I used an app that tells you what order to go on the rides, so you can maximize your time.
Our lodging style is…
a combination of hotels or tenting. The kids love tenting. Our family’s too big to fit in one tent—I guess they do six-man tents, but they really fit four, and they’re usually not as weatherproof. On the last tip our older three boys wanted to be a tent on their own. Mom was a little nervous about that. The six-year-old just wanted to be between us!
My advice for outdoor gear is…
To buy things that are high quality and are going to last. You don’t want to be in a windstorm or something and have things break or leak.
I’d like to get from The Expedition…
New ideas and new places to go. It’s just great to have a group of like-minded people.
I can help other members with…
Answers to questions about the outdoors or anything in my corner of the world. I’m certainly happy to share my secret places.