I grew up in Northern New Jersey, in a suburb of Manhattan, and my family didn’t camp. When we traveled, we chose air-conditioning and crisp white hotel sheets over sleeping bags and the great outdoors. But over the past few years, I’ve dreamed of hopping on my motorcycle with just some clothes, a tent, and a sleeping bag — then exploring.

Day 0: Trip planning

If you’re on Instagram, you’ve probably seen the Wingman of the Road images tempting you in your feed. These rich pics of a solo tent, a motorcycle, and gorgeous mountain ranges have taunted me with the perfect escape. So in May, I decided to order “Goose,” the company’s motorcycle camping tent, sleeping bag, mattress pad combo that all rolls up to a compact duffel. It was designed by riders for riders, and some of the features — such as a helmet hook and a tarp to protect your seat - are thoughtful. The attention to detail here is really exceptional.

But as a new camper, I was a little nervous. I set the tent up in my backyard to make sure I could assemble it (which was incredibly easy; setup only takes around 3 minutes). The forecast called for rain during my ride, and although the tent is made of canvas, which is naturally waterproof, canvas tents need to be “seasoned.” This is a simple process of soaking the tent in water so that the canvas fibers expand and lock in for waterproofing.

My route was simple: Chicago to Traverse City, then ride the Upper Peninsula (or UP) to Minneapolis and finally follow the Mississippi back to Chicago.

Day 1: Chicago, IL to Traverse City, MI via Milwaukee, WI

My first stop was Traverse City to visit Andy, an old college friend of mine. Instead of riding south around Lake Michigan (which is some of the most miserable riding on the face of the planet filled with smokestacks and sulfur odors), I decided to ride north to Milwaukee and take the ferry to Muskegon. The 2.5 hour boat ride was simple as I was able to secure my bike using the tie-downs provided by the crew, and I met friendly rider Pat, who gave me some tips for my route.

Once in Muskegon, I rode north for 2 hours to Traverse City. Andy and I had a beer and some Thai takeout in his backyard. We built a fire. We reminisced. He told me how he regrets blowing off my rehearsal dinner 22 years ago, and how he’s eyeing a used bike. It would be his first bike in 20 years, but maybe he’d buy it so we could ride together next year.

During the conversation, I mentioned how I’d like to trade my 2010 Moto Guzzi in for a newer bike — perhaps a BMW R Nine T. I explained that there’s nothing really wrong with my bike (except a wobbly front wheel from 20-35 mph). Andy explained his rejection of new technology. He cursed his dishwasher with touchpad controls, saying that it was inoperable if he had soapy hands, and he admired his Dad’s dishwasher, which was 30 years old with a big clunky dial used to turn it on.

When the discussion turned to motorcycle trip planning, and how I wanted to avoid the rain, Andy reminded me that it’s all part of riding. The wobbly front wheel. Rain. Other inconveniences — like the moment I had to walk through the McDonald’s drive-thru because the lobby was closed and I needed a coffee — were the things I’d remember about the trip. He was right.

I pitched the Goose tent in his backyard — his family was being extra careful given COVID-19 — smoked a cigar, and went to bed. And I was out.

When I awoke the next morning, I was surprised; the mattress pad was so effective that I didn’t feel sore at all. My only complaint was that the Goose setup didn’t come with a pillow, so I had to borrow my daughter’s compact camping pillow, complete with a big pink ROTHBARD rainbow sticker for easy identification at her summer camp.

There were a few other camping essentials that I had to buy before the trip. I purchased a headlamp so I could see at night and also got a camping chair, the REI Boss. Both the pillow and the chair were able to be rolled up inside the Goose tent for easy transport.

Andy brewed some fresh coffee, and we brought his bathroom scale into the yard to balance my luggage contents across both side bags to minimize that wheel wobble. His wife took a quick picture of us social distancing in the driveway, and I was off.

Day 2: Traverse City to Garden, MI

My next stop was Garden, MI, via Route 31, the Mackinac Bridge, and Route 2. The ride was extremely peaceful. At my true entrance to the UP, I was blown away; I was in rider’s heaven: beautiful trees, perfect conditions, few cars, 65-75mph roads, and rolling hills.

During the ride, I made a point to check in with my family using my SPOT Satellite Messenger. This device allows me to easily check in at home with the push of a button, but more importantly, there are two other buttons that can really help riders in a jam. The first is the “HELP” button, which is used to call a tow truck for minor service issues such as a flat tire or an empty tank. The other button, marked SOS, is to be used in emergency situations. It triggers a 9-1-1 emergency call to send out ambulances or helicopters to assist you.

I arrived at my Airbnb a few hours later, grabbed some fish and chips at The Dock Restaurant, showered, and crashed.

Day 3: Garden, MI to Drummond Lake, WI via Hayward, WI

This was the most beautiful part of the journey. I can explain this leg in two words: pure isolation. I rode through the Chequamegon-Nicolet National Forest. The road was deep in the woods; I was cruising at a good speed and would only see a car only every 5-6 minutes. Planning for gas was important during this part of the trip because there were gas stations available, but without careful planning they might be too far away in a time of need.

When I got closer to Hayward, I took some detours into the woods and scoped out potential places to set up camp. After about 30 minutes of aimless wandering, I found a few that seemed like they’d do. None were perfect but that was ok. Around 4:00 p.m., I headed into Hayward with my stomach grumbling and landed at The Angry Minnow, a familiar joint with food that’s better than the town deserves.

I sat at the bar and had a cheeseburger followed by the Brat Taco (proving that two good things can make one even better thing), then stopped by the local gas station to buy firewood. I strapped the logs to the back of the bike and rode towards Drummond Lake to find a better spot to set up camp.

After some more poking around the national forest for about 30 minutes, I finally found the perfect spot — a small clearing across from a boat ramp – set up my tent, and then shuffled across the dirt road to a boat dock with my chair and a cigar in hand. While sitting outside, I met a father and his two sons from Nebraska. The kids fished from the dock and the father and I discussed riding, fishing, and camping. He suggested that if I ever visit his home state of Nebraska, I should avoid the highway and just ride along Route 20 instead. Good advice for the next time I’m Nebraska-bound.

Though I had the firewood strapped to my bike, I ultimately decided against building a campfire — I wasn’t confident that I could easily contain it. At around 9:00 p.m. I entered the tent and crashed to the sounds of the father-son trio still fishing with only the moon overhead.

Days 4-5: Drummond Lake, WI to Minneapolis, MN then Dubuque, IA

I decided to ride to Minneapolis for some city time — mainly so I could get away from the outdoors and mosquitos, take a shower, and sleep in a bed. So the next morning, I rode back into Hayward and dropped the firewood I purchased back on the rack of wood.

On the way to Minneapolis, I stopped for a coffee and Egg McMuffin from McDonald's. The lobby was closed, and on a motorcycle, a drive-thru isn’t very manageable. So I parked the bike, walked to the window, and asked for a coffee and sandwich. They had me walk to the next window to pay and pick up my breakfast. I’m sure they’re still talking about me.

I then headed to the Twin Cities where I washed off and slept well.

In the morning, I picked my way along the Mississippi River through the towns of Red Wing (yes, where they make the motorcycle boots), LaCrosse, and Prairie du Chien. The first few legs of this trip were incredibly peaceful, riding in the hills of Minnesota and Wisconsin, following the river, and passing very few cars. When I hit Highway 61, I cranked Bob Dylan’s song of the same name through my helmet and headed south.

A few miles before LaCrosse, the temperature dropped about 10° and the sky opened up into one of the most severe thunderstorms I ever rode through. I had to crack my helmet shield a little to prevent fogging as my rain gear was pelted with a combination of rain and hail. In situations like this, your choices are to wait for the storm to pass or push through. I pushed through. In Dubuque, Iowa, I peeled off my drenched clothes (motorcycle rain gear can only do so much) and settled in for the night.

Day 6: Dubuque to Chicago

In the morning, I used a hairdryer to dry out my boots, then got dressed and hit the road for my last stretch home. My gloves were still saturated with rainwater but I pulled them on anyway and then sat on my soaked seat in my damp jeans. I passed solar farms, wind farms, and undulating acres of farmland, and even had a low-flying crop duster cross my path as it worked the cornfields along my ride.

When I finally got to my house, I showered and changed into warm clothes — then went outside to build a fire in my fire pit and relax.