Memories From the Cardboard Box in My Closet: Tales and Photos from Alexandera’s First Winter Bike Tour

In the early years of my bike adventuring, I didn’t have a smartphone and chose to bring a 24-shot disposable camera with me on my adventures to document my trips. I’ve shared a selection of photos from that tour.

I was supposed to ride the Tour Divide in the summer of 2014. I’d learned about the Tour Divide in 2012; that was the year I set out on my first cross-country bike tour. I’d wrapped up that bike tour anticlimactically, searching out a ride back to Wisconsin on Craigslist. I’d run out of money and convinced a stranger driving from Boulder, Colorado to Madison, Wisconsin to let me ride with him. In fact, I told him that I would help drive and that my boyfriend would give him gas money upon my arrival home. I’d accomplished something that I hadn’t even comprehended I could do – I had ridden my bike across the country. Granted, most of that trip was a disaster. I’d set out with the few things I’d already had – a messenger bag, a Blackburn rear rack, 23cc tires pumped up to 110 psi, and little more than that. Oh, but I learned so much…

I’d been obsessively planning my 2014 Tour Divide; I’d even recruited my boyfriend to join me. He’d bought a matching Surly Krampus and we romanticized the adventure to come. He ended up bailing or we broke up, I don’t remember. I ended up bailing too – I didn’t want to ride the Divide alone. I lamented the loss and thought that all my training for the anticipated journey was wasted.

All That Riding Wasn’t Wasted

What I didn’t consider until recently was that my anticipation for the 2014 Tour Divide led me to “train” for, what I thought at the time was, a once-in-a-lifetime adventure. In 2013, I rode everywhere with a Burley trailer attached to my bike to “create resistance.” I had hoped that all that riding with a cumbersome trailern would prepare me for the rigor of the Tour Divide. I was commuting all over the city, always pulling a child trailer behind me.

My best friend, Demi, was my partner in crime. She was “Cycling for Cranes,” raising money for the Crane Foundation that year and I would join her for the long miles. We would pedal across Wisconsin and eventually found ourselves making goals to ride the perimeter of the counties close to us. On one of the fall rides, I recall the temperatures dipping low and being underdressed for the nighttime miles. I did remember to bring gloves, as did Demi, except Demi wouldn’t put them on because she was training her hands to be tough for the winter. Demi is one of the toughest, most determined women I know and is my oldest girlfriend, so when we talked about making a hardcore bike trip across Wisconsin, I had no doubts. It was that evening we decided that we were going to set out on a winter bike tour across northern Wisconsin in January 2014.

The WWW Tour

Winter. Women. Whiskey. That was our plan. We were going to ride our bikes to distilleries in Madison and Minneapolis and make a pit stop at my reservation in northern Minnesota. We had already been planning a weekend-long cross-country ski trip to Minocqua, Wisconsin. That was a perfect location to start our journey. From Minocqua, we planned to take forest roads west to Minnesota and spend a couple of weeks meandering around. Our vision was romantic; snowy miles, crispy air, and whisky-filled bellies. I think our narrative was that whiskey warms the belly, that women can do anything, and that nothing could stop us from riding our bikes. The trip was a hilarious disaster. Demi had bought all of her gear from the army surplus store, and I’d bought crappy gear from Amazon, and we schlepped it into heavy trailers we pulled behind us. 

The reality of our adventure was clouded by the 2014 Polar Vortex, making it inhospitably cold. I didn’t remember a winter so cold– then again, I’d never really spent that much time outside in the deep winter. We’d find hosts on Warmshowers so that we could have the occasional sleep-inside night. Most people thought that we were crazy or homeless, but ultimately, many folks offered us warm beds and hot meals. We even met one fella who pedaled with us out of town for eight miles.

Memories from that Cold Trip

We camped behind a bar in the Chequamegon National Forest on some pallets. The bartender had told us that she was planning on having her dogs sleep inside the house because even the heated barn she had would be too cold. She listened to our story and was so sweet and attentive. When she went back into the kitchen, we thought she was, perhaps, calling her husband to tell him that she would let these two young women camp in the heated barn. Instead, she came out with a thermos of decaf coffee and requested that we “please don’t die; I’ll get in so much trouble for letting you sleep behind the bar.” 

That was the coldest night I ever had slept outside. It was well below zero, nearly forty below, in fact. When it’s that cold, I find myself needing to pee more frequently. I recall holding Demi’s hands as she leaned her butt outside our tent door to pee because we didn’t want to put our boots on during the coldest hours of the night. She would do the same for me. We slept beside each other for warmth. We were there for each other in all the moments of discomfort. Late-night whispers weren’t inconvenient; they were reminders that we weren’t alone, that we weren’t dead. Once the morning arrived, we took down our tent and were encountered by the kitchen staff arriving for their shifts at the bar. One man asked us, “What the hell are you girls doing?” He ran inside to bring us frozen bags of soup to go and told us to “stay warm.” We wandered to a nearby gas station, where we sipped cheap coffee for hours while we warmed up. 

We’d forgo our plans to get to Minnesota and beeline it straight for Madison, some 250 miles away. Most of the roads we’d planned on riding were not plowed. Most of the shoulders we’d needed to use for winter travel were covered in snow and ice. Everything we knew about cycling and bike touring was thrown out the window. 

Fortunately, the route we ended up taking was friendly enough. We’d encounter a restaurant, bar, casino, or gas station every 20 miles or so and stop in to warm up. We’d probably cover 30 miles a day at our best. The hours of light were so short, and the stops grew longer and longer as the cold nipped at our bones. 

One night, just outside of Nekoosa, Wisconsin, we rolled past a casino and planned to stay awake all night so that we didn’t have to sleep outside. We’d planned on a hot meal, warm drinks, and human interaction to keep us up all night. However, the casino was relatively empty, and the restaurant was closed due to the freezing temperatures outside. “People are just staying home,’” the bartender told us. We shared our story with him, and he called in a favor for us. I was vegetarian then, but the bartender convinced a former kitchen staff member, who was still a casino employee, to fire up the grill to make “these badass ladies” a meal. As I ordered my second drink, he ushered us into the closed restaurant lobby to a table with two Reuben sandwiches and two Bloody Marys decorating the table. I ate the sandwich with so much gratitude for the kindness people possessed. 

On another night, a woman who owned a yarn shop said that we could camp inside the store for the evening. We were grateful but kindly declined her offer and asked if we could, instead, camp on her porch. We were trying to prove something to ourselves and were determined to be strong winter campers. She laughed, “alright, ladies, in any case, I am going to leave the door unlocked if you change your mind or need to use the restroom.” We said our “thank-yous” and set up our tent on the porch. In the late hours of the night, one of us whispered to the other, “we are stupid; let’s go sleep inside…” We shimmied out of our tent and curled up like cats on the floor of the yarn shop. We still laugh about this today.

All in all, this trip is one of my favorite memories. I was miserable for most of the hours on the bike. I had chosen horribly inadequate boots for the whole affair. We spent so much more time walking than necessary because we needed to get the blood flowing back to our feet. We had no idea what we were doing, but by going out on a bike trip in country we’d previously toured across in warmer weather, we knew of the familiar infrastructure in the places we pedaled. We could stop at gas stations, restaurants, and bars galore and warm up inside. We slept in the occasional church, and after a mechanical, Demi hitch-hiked into Arlington to fix her bike at Yellow Jersey.  It started to rain as we were just 15 miles away from our “finish line”

The rain was cold, saturating, and froze the instant the drops collided with the pavement. Demi didn’t fix her mechanical entirely and opted to make her ten-speed a singlespeed, leaving her broken derailleur in the garbage at the bike shop. On the infinite climbs between Arlington and Madison, her chain would jump onto a larger cog rendering her bike completely unrideable. We stood on the side of the road while we called for an extraction. Our friend, Michael, came to pick us up, but the roads were so icy his Volvo was struggling to make it up the hills. We’d call it quits so close to the finish.

Most fondly in my memory, though, is my experience of genuinely bonding with another woman in the outdoors. I learned how to trust another person entirely, how to communicate my needs before they become a problem, and how serious winter expeditions can be. It’s taken me almost ten years to feel confident enough to embark on adventures in much more remote places in the winter. Next year, I anticipate spending most of the winter months adventuring in the snow. I’ve become friends with rain in near-freezing conditions, temperatures well below zero, and many different situations. I learned so much more this winter; I can’t wait to see who I meet in the snow next year.