Kentucky to Canada – Our Journey to the CDT’s Northern Terminus

Hi! I’m Sloppy Joe. My husband, Ketchup Daddy, and I are starting our hike SOBO on the CDT!

I’m reminded of how lucky we are to have such an amazing, unwavering supportive family. The days leading up to trail, Garrett’s mom helped us, assembly line style, get our food ready for our resupply boxes. My mom and dad agreed to send our resupply boxes and gear to us throughout the trail. My mom, dad, Aunt Vicki, and Uncle Bob all pitched in to get us to the northern terminus of the CDT. Their generosity and ongoing support positively impacts our experience and mood on trail. Our very own trail angels miles and miles away.


Here we go. We are beginning our road trip north. My mom, dad, Garrett, and I meet my aunt in Ohio, at a point halfway between Kentucky and Michigan. We switch cars and continue north with my aunt. In true serendipitous trail life fashion, the one night we spend in Michigan, happens to be my cousins’ cousin’s graduation party. We are so graciously welcomed and get to fill our bellies with one last delicious homemade meal before setting off on the road again the next morning. (Shout-out to Kiley’s cupcakes, I think I ate six of them).


Up before the sun, we leave Michigan, with our GPS set to Glacier National Park, 27 hours away. I’ve never been on a road trip so long. It gives me plenty of time to remember all the things I forgot to do and pack. I have intrusive thoughts that make me doubt my ability to accomplish such a big feat. Self-doubt slowly creeps in like the shadows of a setting sun. I’m asking a lot of my body. For the third time. Can it hike thousands of miles again? I’m not sure exactly how, but I tell myself I will figure it out along the way. If there’s one thing that the Trail has gifted me, it’s confidence in myself.

While driving through Wisconsin, we are excited to cross paths with a PCT trail friend, Killer. She is a travel nurse working an assignment in Milwaukee, which our route conveniently takes us through. Over a coffee and breakfast sandwiches, we catch up on life and share memories from trail. Her parting gifts to us are well wishes and Wisconsin cheese curds.

After driving 15 hours, we feel satisfied with our progress and pull into a motel in Bismarck, ND for the night.


Fueled by Super 8’s continental breakfast, we continue west. Before crossing the Montana border, we take a detour on the scenic drive through Theodore Roosevelt National Park. As the road winded deeper into the badlands, we were swallowed by tall rock formations. We enjoyed the occasional scenic view. We even drove through a massive Buffalo herd, saw pronghorns and prairie dogs.

As we continued west, the towns became scarce and small. We saw less structures and more crops and cows. Every time we stopped for food or gas and Garrett or I spoke to an employee, they asked where we were from. The subway employee informed me they liked to call this part of Montana,

“Montucky.” About 50 miles out, we wondered when we would see mountains starting to form in the distance. The landscape was flatter than a pancake. It seemed almost instant, one second the horizon was flat, the next peaks were starting to emerge and multiply on the horizon. It was incredible to see the land scape transform from flat fields to an abrupt wall of mountains.

We tented at Looking Glass Hostel. It was a full house tonight with hikers booking up the cabins, sleeping on the floor of the hostel, and tenting in the yard.


6:45 AM, braving the frigid wind and late season snow, we waited outside of the Two Medicine ranger station to get our back country permits. We were first in line. After 20 minutes of piecing together our path with the help of the ranger, we walked away relieved. The rumors were true. The backcountry permit system was a bit of a nightmare and we didn’t get exactly what we wanted. But hey, we’ve got permits to get through the park and that’s all that matters. We ended up with a permit for seven days in the park ranging from short days to medium mile days.

With the remainder of our last day in town, we drive the going-to-the-sun road. It gives us a little preview of what we will be seeing over the next week. Craning my neck to see the tops of the mountains, it’s a mixture of mesmerized and intimated by beauty and size.

We signed up for the Looking Glass Basecamp hostel dinner earlier in the day. Some hikers collected money and offered to cook. I should’ve expected the food to be top of the line, when I learned the hiker in charge of dinner was named Cook. Tonight we sleep in a little hostel cabin and make final preparations to our backpacks. Tomorrow we hike.

Affiliate Disclosure

This website contains affiliate links, which means The Trek may receive a percentage of any product or service you purchase using the links in the articles or advertisements. The buyer pays the same price as they would otherwise, and your purchase helps to support The Trek's ongoing goal to serve you quality backpacking advice and information. Thanks for your support!

To learn more, please visit the About This Site page.

What Do You Think?