2500 Miles Down

August 5, 2025 – Somewhere in South Dakota

I hit 2,500 miles today, the halfway mark.

It feels strange to write that, partly because time on the river moves differently, and partly because the scale of this trip is actually starting to sink in. I knew paddling 5,000 miles across the country would be hard. I didn’t know it would feel quite like this.

Right now, I’m camped on the banks of the Missouri River in South Dakota with a fellow through paddler and my new friend Bob. The sun’s just dropped below the horizon, and everything’s gone quiet except for the wind brushing through the grass and chirping of the crickets.

This feels like the right place to stop and take a breath.

I’ve been out here long enough that my canoe and my tent feel more like home than anywhere else. The boat is worn in, my hands are permanently weathered, and I can feel the change in the air on my face when a storm’s about to roll in. But no amount of experience makes the next half of this trip feel any smaller.

This journey has been hard. The physical part is constant, long days paddling under a hot sky, my back and shoulders never seem to fully loosen up, and small injuries that don’t get to rest. A sore wrist here or stiff leg there are things you’d shrug off on a weekend trip but don’t just go away out here.

But the hardest part, more than the weather or the logistics or even the blisters, is the mental side of it. Waking up sore and tired, knowing I’ve still got thousands of miles ahead of me. Trying to stay positive when the wind turns against me, or when a storm system parks itself over my route for days. Or when I’m  paddling along in silence and the only thought in my head is: Why am I doing this again?

That question shows up more often than I care to admit. But I’ve learned not to treat it like a threat, it’s more of a checkpoint. When it comes, I sit with it. I let it hang around and I remind myself that I chose this. That there's something important in pushing through the doubt instead of running from it.

Tip2Tip has been full of surprises. Some good, like a stranger handing me a cold drink from a pontoon boat. Others not so great. Like windy days that I have no choice but to sit and wait, or storms that blow through camp in the middle of the night, snapping tent poles.

But even on the hardest days, there’s been something to hold onto.

One of the real highlights of this trip has been the kindness of strangers, river angels, as we like to call them. I’ve been met with more generosity than I could have imagined. People I’ve never met from all walks of life and everywhere on the political spectrum, who owe me nothing, have offered food, shelter, encouragement, and gear fixes without hesitation. That kind of kindness doesn’t just help me get down the river, it reminds me why I’m out here in the first place. To meet the people.

There’s still so far to go.

After I finish this section of the Missouri, I’ll hit the Mississippi, and from there head south, toward the Gulf. I’m still not sure if i will be taking the Tombigbee/Tennessee River route yet. Eventually I’ll paddle east, aiming towards the southwestern tip of Florida, still months away, still hundreds of thousands of paddle strokes to go.

I try not to think about the full distance too often. It’s too big to hold all at once. Most days, it’s just about finding water, staying safe, keeping the boat pointed the right direction, keeping the bottom the bottom, and getting through another 20 miles… And then doing it again tomorrow.

The truth is, this trip has already changed me, not in any dramatic, life-reinventing kind of way, but subtlety. In how I’ve come to expect that things will go wrong and learned to move forward anyway. In how I’ve stopped needing to control every part of the plan.

To everyone who’s been following along, sending messages, chipping in for gear or food or just checking the tracker, thank you. I don’t say it enough, but this would be a very different journey without your support. Every encouraging word makes its way into the boat with me. Every bit of kindness helps drive my paddle one stroke more.

A special thanks to the sponsors who believed in this journey from the beginning: Rutabaga Paddlesports, Swift Canoe & Kayak, Fits Socks, Falcon Kayak Sails, Level Six, Redleaf Designs, your support, your gear, and your belief in this trip have made a huge difference. I’m proud to carry your names downstream

So here I am, halfway through a 5,000-mile paddle across the U.S.—a little bruised, a little sunburned, but still in it.

Still paddling.

Still believing this thing is worth finishing.

—Kyle