Montana. And Hitchhiking on Craigslist

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Me and Matt. In Fernie, Canada

August, 2019

Just a few short days after returning home from the Vermont Gravel Growler, Matt & I were ready for part 2….

…a 3 day, 2 night bikepacking loop in the northern Montana mountains followed by a few days in Canada to meet up with a couple of Matt’s friends. Following our Montana cycling loop, we’d head up to Calgary to pick up a reserved rental SUV, which would become home for us as we explored the famous Banff & Jasper National Parks on the border of the Alberta & British Columbia provinces of Canada. We’d then return the rental and fly home from Calgary. Sounds simple enough, when listed that way.

You may have noticed that I did not mentioned how we’d get up into Canada from Montana. This is because we had no plan. Google maps said it was a 5ish hour drive from Whitefish, MT to Calgary, Canada. One-way rental cars weren’t an option because we were crossing an international border; hence the rental from Calgary. Flights seemed wildly expensive for the distance covered, and all flight options had connections in out of the way cities, like Seattle. We figured, ‘eh, people must make this drive all the time. Someone in Whitefish will have an idea of how to get up to Calgary.’ This is an important time to note that not all ideas are good ideas.

With a bit of bikepacking experience under our belts, we felt good heading into another adventure - this one a bit more remote & in a place brand new to both of us. We’d follow the Red Meadow Pass loop, again borrowed from the great folks at Bikepacking.com. Instead of flying with our bikes, we opted to rent mountain bikes from a local bike shop in Whitefish, MT. Our travel logistics (or lack thereof) would have made lugging bikes around more complicated. Beyond that, the concept of flying with a bike felt intimidating. So, bags packed, we jetted off.

We gave ourselves one full day to get situated in Whitefish before heading out on the bikes. We’d be out riding for the next two nights, then finish up with a morning ride back in Whitefish. We’d use that same afternoon to return the bikes, clean ourselves and our gear, and pack up for Canada - our scheduled car pick up in Calgary was the following afternoon.This meant that we really only had this first full day in town to figure out how we’d be getting up to Calgary, as this already challenging logistical problem would only be harder to solve once out in the woods.

We stayed at an AirBnB, where our host was named - in all seriousness - Life Everlasting Noel. He was a total oddball who owned way too many cats and loved sharing stories of late night, under the table poker games, but he was a genuinely kindhearted human who went out of his way to ensure we felt comfortable at his place. It was Life who let us know that, in fact, not many folks make the drive from Whitefish to Calgary, nor was there a shuttle or taxi service. Uh oh. Life advised us that he thought folks posted ride share opportunities online pretty frequently, so we could at least put ourselves out there that way. So, in the best way we knew how, we did. Craigslist.

Now fully packed up for our bike trip, Matt and I headed out to dinner, where we had maybe just one too many beers. At this point, we decided to pull the trigger and write up a post for the ride share section of Craigslist. While the original post has been lost to the ether, the gist of our write up was as follows: 

We’re a couple of fun guys who like bikes and need a ride up to Calgary on xx day. Willing to chip in for gas money and snacks, and will tell funny stories the whole way up. Also, sometimes we like to fart with the windows up.
— Conor and Matt

This executive summary of our personalities was accompanied by a single goofy photo of the two of us from some point in our past (we didn’t have too many serious looking photos together, turned out). Funny & to the point, right? This could only attract likeminded folks. With the post now live, we headed to bed, confident that over the next couple days, somebody would get a kick out of us and drive us to Calgary, and we’d get a good story out of this. We were half right.

Lunch spot at Red Meadow Lake

Lunch spot at Red Meadow Lake

We were up early the next morning to ride out. Fifty miles of dirt forest roads through the mountains. One big climb up to Red Meadow Lake, Matt bumping tunes from our portable speaker the whole way up. At the top, we stopped for a long lunch and quick swim at Red Meadow lake. We continued onwards into the afternoon and descended into the tiny town of Polebrige, MT, which boasts a single mercantile and neighboring saloon as it’s only public buildings. In the waning light, we settled in to pizza and beers from the saloon with a handful of other bikers passing through - a couple folks on electric bikes, and a couple others on touring dirt motorcycles. We found a perfect spot to pitch the tent for the night about a mile from Polebridge, and without any light pollution slept under a brilliant starry night.

Finishing the climb.

Finishing the climb.

Bowman Lake.

Bowman Lake.

After a legendary huckleberry bearclaw pastry for breakfast from the Mercantile (cyclists get one free!), we pushed onwards into Glacier National Park. Once in the park, we went out of our way for a ~6 mile out and back to Bowman Lake, where we spent the better part of a couple hours basking in the awe inspiring landscape with just a handful of other folks in this remote area of the park.

What followed was 30ish spectacular miles along an old forest road now closed to motorized vehicles. For hours, we saw nobody else. No cars. Just us. It was bliss. We alternated between silence and tunes along the way as we slowly approached the small town of Apgar, soaking in the vivid greens of the trees and the occasional glimpse of the jagged Rocky Mountains just off our east flank. In my journal on this day, I wrote, in all caps “I NEED TO DO THIS. ALWAYS.” I can’t think of a better way to sum up that feeling.

The Polebridge Mercantile. And Me. Thanks, Matt.

The Polebridge Mercantile. And Me. Thanks, Matt.

Our second night was in a campground in the tourist town of Apgar, where we had takeout dinner and beers overlooking the enormous Lake McDonald. A rainy, paved 30 miles took us the rest of the way back to Whitefish in the morning. Despite the rain, we were riding high coming back into town, giddy with excitement of what we had been able to experience under the power of our own two legs. We concluded that bikepacking is, indeed, the best way to see the world.


Three. That’s how many replies we had to our Craiglist post upon our return to Whitefish.

The first reply was a generic message that seemed to be automated, so we disregarded it. The second reply offered sexual favors in return for a ride, which we got a good chuckle at but also disregarded. The third reply seemed promising. A guy named Ron sent us an earnest message saying that he loved the drive up to Calgary and had done it many times before. He’d be happy to drive us across the border up to our destination, and he left us his phone number to confirm. Matt gave Ron a call to talk it through. We’d pay Ron $200 (less than half the price of any flight), and he’d pick us up at a local coffee shop at 8am the next morning. Easy peasy. We were all set….right?

Red flag number one. Ron’s late.

Matt and I arrived at the coffeeshop at 7:30am to get some breakfast in before our pickup. Eight o’clock rolled around, no Ron. Then 8:30...no Ron. Matt calls Ron, who quickly apologizes for being late but confirms he’s on the way. Just before 9, Ron rolls into the parking lot in a janky red mid 90’s crew cab Toyota pickup (the kind with just three seats across in the front). Matt and I exchange a look that clearly says “I don’t want to sit in the middle.” As Ron makes his way over to us, we quickly flip a coin to determine who has the good fortune of the middle seat for the 5 hour ride. Matt loses. Poor guy.

Red flag number two. Ron lets us know he forgot his driver’s license & passport at home, which he’ll most certainly need to cross the border.

Do we want to tag along for the half hour ride back to his house, and then we can all leave from the house together, he asks? We most certainly do not. Did Matt and I think this whole situation was odd? Absolutely. Did we have any other realistic option at this point? We did not. Matt and I let Ron know that we’ll happily wait for him another hour at our outdoor coffee shop table in the sun. 

Finally, we begin our journey northward with Ron just after 10am.  Still ample time to get to Calgary before our rental car place closed down for the night. Look at us, giving ourselves a buffer. Genius!

It was 2.5ish hours up to the border, then another couple hours to Calgary. For the first two hours, Ron talked at us (not to us...there is indeed a distinction, as anyone who has been on the receiving end of an ‘at us’ conversation can attest). He gave us a more detailed than needed life story, including many stories of the highs and lows of late night poker games (a theme in Whitefish, it now seemed to us). As we were already well into the drive, Matt & I forked over the $200 to Ron at Ron’s request. Seemed fine - we were already driving, right? Definitely should have held off on payment until after we were in Canada.

Red flag number three. Not that we can do anything about these red flags anymore...we were in it now. As we began to see signs for the border, Ron’s behavior changed. We could feel his nerves, and he became fidgety. Ron elected this moment to let us know he hadn’t actually done this drive in many years. Interesting. He also lets us know he doesn’t even have a passport - just a birth certificate, which he assures us will be fine. Even more interesting.

Finally, we roll up to the agent at border patrol. Immediately, and without prompting from the agent, Ron turns the car off and informs the agent know that he just met the two of us from a Craigslist ad, and he’s giving us a ride up to Calgary for $200. A weird move, certainly, but seemingly inconsequential in the moment. The agent wanted proof of our relationship; we showed him the Craigslist ad. Now the agent probably thought that the two of us were weirdos too, but at least he could be sure we didn’t know Ron in any capacity beyond this ride. Now knowing how things would soon play out, we had to give kudos to Ron for separating himself from the two of us immediately. Perhaps his only redeeming move in this adventure.

The agent took our documents and disappeared into the building. After a couple minutes, the agent returned to ask us to pull into an inspection site, step out of the vehicle, and stand alongside a table. Uh oh. Not good. Ron, Matt and I do as instructed and step up to the table to meet the border agent, hearts beating faster and faster. We’re asked to turn out our pockets and put everything on the table. Matt and I are nervous, but have nothing to hide, so do as instructed. Ron does the same...and produces a small white medicinal vial. Curious.

The agent takes the vial, looks it over quickly, and then asks Ron, ‘how long have you been in recovery for heroin?”. Matt and I exchange another look - big eyes, raised eyebrows. Oh boy. Ron stumbles through a convoluted response that doesn’t really answer the question. The agent responds by stating ‘typically the person in recovery has the vial of the methadone prescribed in their own name.’ Out of the frying pan, into the fire.

The agent asks Ron to join him inside the building, and for Matt and I to sit outside on a little bench. Another agent with a dog comes out, and we watch helplessly from the sideline as Ron’s truck (and our bags) are torn apart in a thorough search. After a few minutes, we hear the agent searching through the truck use his radio: ‘get the heroin kit ready.’ Ah, perfect. 

For the next 45 minutes, Matt and I sit there on the bench, swinging our legs, wondering how on earth we’re getting out of this. We’re confident we won’t get in any trouble, thanks to our trusty Craigslist proof that we don’t know Ron, but our options are limited...there is only one souvenir shop at the border, and the closest town on either side is over 20 miles away.

Finally, the first agent we spoke with came outside again. He let us know that Ron would be spending at least the next few hours in questioning. And the truck? That thing would never get into Canada, he assured us. We were on our own. Oh, and no, we couldn’t get our $200 back from Ron. He had bigger problems to worry about. Yup, that seemed fair. The agent confirmed that there were no taxi or shuttle services to help out, but did say that if we brought our bags to the far side of the cones that marked the end of border control into Canada, there was nothing legally preventing us from a hitchhiking attempt. Welp, here goes nothing!

For the next couple hours, Matt and I excitedly tried to swoon the drivers of any of the dozens of vehicles crossing the border into Canada. Lots of smiles and waves, but no luck. As hopes began to dwindle and the reality that we may have to head back southward began to set in, we struck gold. A middle aged man from Virginia, on a business trip to the town of Fernie (the closest Canadian town to the border) stopped to give us a lift. He saw our large packs, and having been a backpacker himself in his youth, had relied many a time on rides from strangers and wanted to pay it forward. Thank. Goodness.

We arrived into Fernie, our driver’s final destination, with a couple hours of daylight left. With the smallest glimmer of hope of catching another ride the final hour to Calgary, we handcrafted some signs, grabbed some McDonald’s, and posted up near the final stoplight of town along the main road north. No luck. Ah well. We did some quick google searching to find a hotel for the night, and settled in to a surprise night in Fernie. Which, we’ll be the first to tell you, is one of the most beautiful towns we’ve had the pleasure to visit. Nestled right in a valley surrounded by enormous mountains, it’s a hub for outdoor enthusiasts of all kinds. Highly recommend!

Fernie!

Fernie!

In Fernie, enjoying McDonalds, attempting to hitchhike to Calgary.

In Fernie, enjoying McDonalds, attempting to hitchhike to Calgary.

Listen to Matt’s retelling of our hitchhiking story on the After School Program podcast on Spotify!

We spent the evening arranging a shuttle service for ourselves up to Calgary for the next morning, and adjusting our rental pickup for our late arrival. All in all, we ended up spending just about the same amount of money we would have spent on a flight from Montana up to Clagary. But, we did get a heck of a story out of it...so we were half right!

Finally arriving into Banff National park a day and a half later than planned, we recounted our adventure to Matt’s friends, who couldn’t believe what we’d gotten ourselves into. Frankly, we couldn’t believe it either. We became the butt end of many a joke over the next few days as we went on day hikes through the mountains, squeezed in a couple day rides on rental bikes, and found beautiful pull off spots to car camp.

It felt all too soon that we were back in Calgary, returning the car, and hopping on a red eye flight back to the east coast. What a whirlwind of two weeks. A trip that won’t soon be forgotten!

Lessons learned…

  1. Bikepacking is indeed the best thing ever.

  2. The Rockies in Canada and Montana are home to some of the most beautiful views on earth.

  3. Craigslist can be a great resource, but not for rideshares.

  4. Fernie, Canada is a place to add to everyone’s travel list!

Hiking in the Canadian Rockies

Hiking in the Canadian Rockies

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