My Adventure: by Dale Simonson
For more than 40 years, my older sister Kris and I lived on parallel tracks. We loved each other, called on birthdays, and gathered for the occasional holiday. But work, family, and the general busyness of life kept us from really knowing each other as the adults we’d become. This year, we decided to change that. With Kris’ arm-twisting (it didn’t really take much twisting), I signed up for the Border Route Challenge and set out to paddle it together.
If you haven’t heard of it, the Border Route Challenge is a classic canoe-country journey along the international boundary between Minnesota and Ontario, Canada running through the Boundary Waters Canoe Area Wilderness and ending at Lake Superior. The informal annual challenge, held each September, offers several route lengths, from about 125 miles up to the full 260, including dozens of portages between lakes totaling about 19 miles of canoe-carrying.
The entire journey took us 5.5 days, plus another 2 days of traveling to/from the route together. Those days on the water have a way of stripping life down to the essentials. There were no meetings, no notifications, and no to-do lists. Just Kris, me, a boat, and the next stretch of water to paddle or land to portage. We paddled across glassy lakes, hauled our gear over rugged portages, and fell into a rhythm where one of us would call out a rock or a route choice and the other would adjust without a word. Somewhere along the way, I realized we were reconnecting in a way we hadn’t since we were kids.
What made it special wasn’t only the scenery, though the scenery was spectacular. It was the uninterrupted time together. Hours of paddling leave plenty of room for conversation, and just as much room for comfortable silence. We talked about our childhood, our parents, our kids, and our dreams. We laughed about things only siblings remember. We also leaned on each other when we were tired, sore, hungry, or grumpy. I learned things about my sister I never knew, including how tough and determined she is. I think she’d say the same about me.
When we reached the end, we weren’t just finished with a challenge. We had closed a gap that decades had quietly opened between us.
Advice to Others:
If this story stirs something in you, here’s my encouragement: call your sibling. Or your parent or kid, your cousin, your best friend… Then pick something big, challenging, and away from the hustle and bustle of daily life. And do it together. Here’s what I learned along the way.
Choose an adventure that gives you time together. Paddling is ideal because you’re stuck in the same boat together for hours, traveling at the same speed with nothing to do but move forward and talk. Hiking, cycling, and backpacking offer a similar gift. The point is to find something that unplugs you both and keeps you together long enough for real conversation.
Pick a challenge that stretches you, but not past breaking. Events like the Border Route Challenge offer different distances, so you can match the route to your experience and fitness. A goal that feels slightly intimidating gives you something to train for and talk about for months. That shared buildup becomes part of the adventure, and the feeling of accomplishing something hard gives you a shared sense of achievement.
Prepare together. Training, packing lists, route planning, and gear shopping all bring you closer before you ever touch the water. Divide tasks based on your strengths, and be honest about your limits. Wilderness travel rewards good planning and respect for the environment. Really, the preparation together can be as meaningful as the journey itself.
Embrace the hard parts. There will be moments when you’re tired, wet, cold, or frustrated. Those are often the moments you’ll remember most fondly. Struggling alongside someone and getting through it together builds a bond that a nice restaurant dinner never could.
Don’t wait for the “right time.” I spent four decades assuming there would always be another chance. There’s never a perfect moment, only the one you choose. Life gets busier, bodies change, and opportunities narrow. If I could tell my younger self one thing, it would be to stop saying “someday.”
Sharing a big outdoor adventure with a sibling gave me something I didn’t know I was missing: a deeper, more present, more joyful connection with someone who has known me my whole life. We came home with sore shoulders, great photos, shared memories, and a bond that’s stronger than ever.
So grab your person and find your adventure. Seize the day, together.
