A picture of a person riding a bicycle along a forested trail

Lessons From a Bike Ride Across Minnesota (the Long Way)

Where did the journey begin? Sometime in the depths of last winter, I found myself down a rabbit hole on the webpage for the Minnesota Department of Transportation’s (MnDOT) State Bicycle Map. The state bicycle map is an interesting but incomplete resource, but included on the map and webpage for State Bicycle Wayfinding are Minnesota’s United States Bicycle routes: the Mississippi River Trail (MRT, or U.S. Bicycle Route 45) stretching from Lake Itasca to Venice, Louisiana, as well as the North Star Route (or U.S. Bicycle Route 41), leading from the State Capitol in St. Paul to the Canadian border along Lake Superior.

Snowed in and bored, that’s when I probably started dreaming of it: I could ride a bicycle across Minnesota — the long way. There was a route, put together by MnDOT no less. Now this was a ride. It appealed to my ego and “homerism”: I could say I biked across the entire state, the long way. It appealed to my (malicious compliance? spiteful suggestibility?): MnDOT says there’s a bike route, so I’m going to bike it. And it was just crazy enough to appeal to my little brother, Grant, who is crazier than me.

We hatched a plan. Upon his graduation from Carleton College (in Northfield, Minn.), we’d start at the Iowa border and make our way up the Mississippi River Trail until we hit the metro area. From there, we’d blaze a path over to the North Star Route, which would take us to Duluth, up the North Shore of Lake Superior and to the Canadian border at Pigeon River.

The scheme was set, the route was studied — but not finalized, and things started to go awry.

In January, I found a pre-order deal on a road bicycle that I believed would be great for both long hours in the saddle and loading down with bags and other supplies. The bicycle was not ready in time for June (the supply chain), so I had to press another bike into service: my purple commuting bicycle, a Handsome Devil that I believed to be up to the task, but not necessarily optimized for it. Grant, meanwhile, unimpressed with the length and breadth of the itinerary, decided he wanted to continue on from the border, and tack on the Lake Superior Circle Tour on top of our trip — all on a bicycle. So he got busy outfitting a bike that would have to carry days’ worth of camping supplies, food and other Canada stuff once I had peeled off.

We planned about a week’s schedule of biking and lodging for Minnesota, because I wasn’t able to carry camping equipment, or very enthused by the prospect. Plus, we know enough folks along the route, across Minnesota, who would be willing to offer shelter that we opted for the “touring” approach over “bikepacking.” The projected start day approached, and although we did what we could to prepare, we had no idea if we were ready.

The author's brother on his bike at the side of a road, next to signage for Minnesota Highway 61 and the Lake Superior Circle Tour.
My brother, Grant, who was my travel companion. He is, at publication time, currently continuing on the Lake Superior Circle Tour by bicycle.

First, some caveats and disclaimers:

My brother and I are both in our 20s. We are able bodied, and part of the inspiration for this itinerary is that we felt comfortable and confident doing it at this age, in these bodies. I’m a daily bike commuter/lifestyle biker, but neither of us necessarily trained for this trip. That’s a privilege, or blessing, depending upon how you look at it. In terms of diet, we packed lots of snacks — including those sugary so-called “energy chews” — but as it turned out, we did not snack all that much. Instead we ate three square meals a day, often from local restaurants along the way. With a little research for locations and operating hours, we were able to find farmer-style breakfasts at affordable prices at local establishments. While I’m usually a light breakfast eater, eggs, extra hash browns and Minnesota’s numerous breakfast specials were integral to my completion of this trip. Dining out also allowed us to stop more often throughout the day, and stop in towns we would otherwise have just pedaled through.

We were never too far away from help — and used some, too. We have family in the Twin Cities, close family friends in Duluth and friends across Minnesota. Spoiler alert, we didn’t end up needing all that much help, but it boosted our confidence to know that if we got into a really sticky situation, the odds were that someone could be within a day’s drive to help or extract us. Special thanks go to our mother Julia, who saw us off to Iowa, joined us for a day to enjoy Grand Marais and then retrieved me from the Canadian border. She would have joined us for longer if we had been able to schedule the trip during a week when she was not working. Props, kudos and recognition also goes to our father Skip, who biked with us for the first two days and 140 miles, from the Iowa border to Hastings, and helped us for our warm-up ride.

The trip was not exactly car-free. Our mother dropped me, my brother and father off at the Iowa border in New Albin, Iowa. I was picked up from the Canadian border in Pigeon River. There are opportunities for car-free bike touring, and many more will come more easily to fruition with recent Minnesota transportation developments such as the Northern Lights Express and the Great River Rail. But you can’t call what I did a car-free vacation.

Someone had experience. Grant had never attempted a trip of this length, but he had done a Minneapolis–to-Grand Marais trip by bike, so a large portion of the route was familiar to him. While it wasn’t necessary, it was great to travel with someone who knew the way for those segments.

Our maps were out of date! I used the most recent version of the Minnesota portion of the Mississippi River Trail Map, which was from … 2015. I did not even bother with a North Star Route map, which must have had a similar vintage. Largely, the route was as mapped, but I was very aware that the maps reflected a reality from nearly a decade ago.

I’ve included short descriptions of the days, with highlights and lowlights and distances. Lessons I learned are sprinkled in. These descriptions are not detailed enough to be used for navigation, so if you’re planning a similar trip, I encourage further research and checking out the resources provided by MnDOT, nonprofit organizations, trail associations and national organizations such as the Adventure Cycling Association. I also included featured bike and multi-use trails, because there are great segments across the state that are worth riding — and maybe even extending and connecting.

Here is our story, told through the itinerary and the lessons from each day.

Day 0: New Albin, Iowa, to La Crosse, Wisconsin. 27 miles

Strava map showing the route from New Albin, Iowa to La Crosse, Wisc.

This was our warm-up day, and we did the ride in the afternoon after our ride dropped us off. We followed the official route of the Mississippi River Trail through Houston County, from New Albin, Iowa, to La Crescent, Minn. The dated map had warned me that the shoulders were narrow here. That was still true, but it ended up being almost a non-issue. The traffic was sparse, and the drivers who did pass us were very courteous.

Lesson: Given that we anxiously eyed the shoulders on the way down, our first 27-mile ride was a huge confidence boost, and a beautiful ride through the southernmost reaches of Minnesota.

Warning: Narrow shoulders.

Highlight: First day, and we did it! Plus, La Crosse is a great town to drink a beer in. (La Crosse claims to have the most bars per capita in the United States, and while there is no reputable source to corroborate that claim, it’s very easy to find a bar — or several.)

Featured trails: None.

The author and his brother with their bikes at the Iowa border, next to a sign reading "The People of Iowa Welcome You."
The author (left), with his brother and travel companion, at the beginning of their journey in New Albin, Iowa.

Day 1: La Crosse, Wisconsin, to Wabasha, Minnesota. 70 miles

Strava map showing the route from La Crosse, Wisc. to Wabasha, Minn.

OK. So you already caught me in a lie. We did not ride the entire way across Minnesota. Between La Crosse and Winona, we took the 30-mile Great River State Trail. This gravel/natural surface trail follows a former railroad right-of-way and is maintained by the Wisconsin Department of Natural Resources — so it’s on the Wisconsin side of the river. While I was worried about the miles in Wisconsin negating the concept of the ride, the Great River Trail is absolutely worth it. Traveling over winding rivers and through now-protected wetlands, the trail’s tranquility and natural beauty can’t be compared to a highway shoulder. After a great lunch at Beno’s Deli in Winona, we made our way up the Minnesota side. This time it was a highway shoulder, but we’d depart from the shoulder of U.S. 61 to follow the MRT along the levee north of Winona, or through the Weaver Dunes.

Warning: There’s not enough signage between the end of the Great River Trail in Wisconsin and the start of the Flyway Trail in Winona. Highway 61 has a wide shoulder, but you will have to get used to riding alongside 60 mph traffic. The Wisconsin DNR requires a trail pass for the Great River Trail. My father’s road bike tires worked fine for the uneven surfaces of the trail, but with preparation you’d want slightly wider tires.

Highlight: The Great River Trail was a surprise and a joy.

Two cyclists riding down a dirt tire-track trail.
The Great River Trail, in Wisconsin. It continues like this for miles, with a number of bridges and wetlands.

Featured Trails: Great River Trail (Wisconsin), Flyway Trail (Winona, Minn. and Buffalo County, Wisc.)

Day 2: Wabasha, Minnesota, to Stillwater, Minnesota. 88 Miles

Strava map showing the route from Wabasha to Stillwater.

The MRT is superbly signed. They get every turn: before, so you know where to go, and after, so you know you took the correct turn. So why did we leave the planned route? Because we’re idiots.

The first 40 miles along the MRT were great. We stopped for breakfast along Lake Pepin, where we had coffee at the Rustic Coffeehouse in Lake City, and got to chatting with a retired policy aide from Missouri, who worked on water quality and conservation in the 1960s and ’70s — long before those issues were mainstream. But after Red Wing, we blazed a path off the MRT for Treasure Island Casino. Mind you, we are not big gamblers. I have better ways of burning money. Like on bikes, or underdog organizations doing good work (donate to Streets.mn!). But the story is, I had a coupon for a generous portion of free slot plays, and we all thought it would be funny if we made a detour to the casino to use the coupon on our cross-state bike trip. We’re a fun crowd.

The author, his brother and his father with their bikes by the Hastings lift bridge.
Diverging paths with our dad at Hastings.

Lesson: Some things make for better stories than actual experiences. I burned through the funny money, and I hardly got a second glance wearing bike shorts on the casino floor, but the route was awful. We had a terrible climb over the river bluff from the MRT to the casino, and then a nerve-wracking, prayer-inducing vanishing shoulder from Treasure Island to where we rejoined the MRT in Hastings. Having not learned our lesson, we departed from the formal route again north of Hastings and blazed a path through southern Washington County, rather than take the more roundabout route through St. Paul on the way to Stillwater. The sun was out, and the shoulder was non-existent, but that wasn’t the problem. The problem was the hills.

There are a lot of hills between Hastings and Afton. More than you’d expect. More than you can reasonably predict to your brother before he gets really mad at you for offering that “this might be the last hill before Afton.” But once you get to Afton, you have a lovely route along the Afton to Lakeland Trail that gets you much of the way to Stillwater on trails and wide shoulders.

Warning: Be very careful blazing your own path. Don’t trust Google.

Highlights: Riding the shoulder along Lake Pepin, the relatively level Afton-Lakeland Trail.

Featured Trails: Hastings trails, Afton to Lakeland Trail.

Day 3: Stillwater to Hinckley. 79 Miles

Strava map showing the route from Stillwater to Hinckley.

Despite my frantic warnings about blazing your own path, our improvised route from Stillwater to Hugo worked well. The Brown’s Creek State Trail is an excellent route out of Stillwater and got us halfway there before we diverted to follow a narrow-but-quiet highway shoulder to Hugo, where we met up with the Sunrise Prairie Regional Trail. Not always the most scenic, it’s nevertheless an impressive trail that spans 30 miles between Hugo and North Branch. We also were impressed by the quantity and diversity of people riding the northern portion: folks of all ages, riding all manner of equipment and, to the extent you can say this in central Minnesota, of many ethnicities. We continued along Highway 61 north of North Branch and got to yearn for the trail under construction between North Branch and Harris. This was the day of catastrophic air pollution from the Canadian wildfires.

Lesson: As we observed our diminishing visibility, we put on N95 masks, which we were able to comfortably bike in for the remainder of the day. Fortunately, the air quality had cleared for northern Minnesota by the next morning.

The author wearing an N95 mask and bike helmet under visibly smoky conditions.
The author, masked in North Branch, Minn.

Warning: Wildfire smoke can cause cancer(s).

Highlight: The Sunrise Prairie Regional Trail is a well-used community resource, and getting longer as I write this.

Featured Trails: Brown’s Creek State Trail, Sunrise Prairie Regional Trail

Day 4: Hinckley to Duluth. 87 Miles

Strava map showing the route from Hinckley to Duluth.

This was the easiest day, both navigation and riding-wise. You get on the Willard Munger State Trail, which starts in Hinckley, and then ride it north to Duluth. There is no second step. For the last 20 miles or so, between Carlton and Duluth, it’s a generous downgrade, so the riding is easy. Willard Munger is a rail trail, so you travel through the heart of the towns in Pine and Carlton counties. You get to watch as the land transitions from farmland and wetland to northern forest and the dramatic elevations of Duluth. Back in the day (2020) the Munger Trail was my first experience with biking distances, and I’d recommend it (especially northbound) to anyone who wants to dip their toe into bike touring. The day started cool, barely 50 degrees, and it stayed a merciful temperature for the rest of the day. At this point, I was feeling so confident that I took a detour to visit a dear family friend at Farm LoLa in Wrenshall, which added about 7 miles to the trip. In Duluth, I took the new gravel Waabizheshikana (The Marten Trail) as a substitute for the temporarily closed Cross City Trail; the new trail is an impressive endeavor whose quick-build execution puts some major Minnesota cities to shame. 

Warning: The towns are tiny, and if you miss them, too late!

Highlight: Miles of trail is miles to goof off with your little brother. If you are riding on a warm day, there’s a great swimming hole on the Saint Louis River right east of Carlton. Spot the bike racks along the trail, follow the locals and you’ll find it.

A single cyclist riding down a paved bike path, trees on either side.
The Willard Munger State Trail is expansive and quiet.

Featured Trails: Willard Munger State Trail and the Cross City Trail in Duluth

Day 5: Duluth to Lutsen. 96 Miles

Strava map showing the route from Duluth to Lutsen.

So, this was when planning went off the rails. We may have waited a bit too long to get lodging. That was no problem for the river towns of southern Minnesota during the week. But our delay in booking lodging along the North Shore for the weekend of Grandma’s Marathon — when no one would accommodate a one-day booking — was a big mistake.

Lesson: Book weekends and prime-time tourist locations as early as feasible. Not only could we find no affordable lodging, but we couldn’t find any lodging that was open to single-night guests in a ride-adjacent location. We got lucky in that we have a great friend in Lutsen who let us crash at his home. But Lutsen is nearly 100 miles north of Duluth, along the undulating shores of Lake Superior. So Day 5, Duluth to Lutsen was both our longest day and our day with the most elevation gain. It was also the day that I got the first flat tire of the trip.

The author fixing his flat.
All told, not the worst place I’ve ever had to deal with a flat tire.

Honestly, in my memory, it wasn’t a bad ride. My bike began to make noises, which became a problem later. And we got a later start than was wise. But we covered the distance, took breaks and got to Lutsen before dark. And along the way we got to experience the incredible scenery and trails along the North Shore of Lake Superior.

The Gitchi-Gami State Trail is an ambitious endeavor, envisioning a trail along almost the entire North Shore. Currently, it exists in a handful of disconnected segments, mostly adjacent to population centers along the shore, and on land owned and managed by the Minnesota Department of Natural Resources (DNR). But the existing segments are worth experiencing, and we witnessed multiple areas of construction where shoulders were being widened, or bridges were being constructed with multi-use path bridge decks built in — even if the trail hadn’t made it there yet. There are lengthy sections from Gooseberry Falls State Park through to the far side of Split Rock Lighthouse State Park, from Beaver Bay to Silver Bay and Tofte to Lutsen. And behold, the ride is magnificent. 

Warning: Lodging prices and highway traffic increase dramatically on summer weekends, and some shoulders are not super fun. They may be narrow, penned in by guardrails or at a low-visibility point on the numerous bends and weaves along Highway 61.

Highlight: The big lake is right there.

Featured Trail: Duluth Lakewalk, Gitchi-Gami State Trail.

Day 6: Lutsen to Grand Marais. 20 Miles

Strava map showing the route from Lutsen to Grand Marais.

Yes, due to my bad planning, we had a nearly 100-mile day followed by a day where we barely went 20 miles. But Grand Marais is not just a cute town. It’s an underrated bike town. I appreciated spotting bikes — and bike racks — almost everywhere.

But by this point the bike I was riding had gone from making sounds to visible crank issues — which is to say, the part the pedals and gear are attached to had a sliver of daylight between the frame, which is the part that holds the handlebars and the seat and you ride on. So that’s not great. Grand Marais is a happening town, and according to the employee I talked to at Stone Harbor Wilderness Supply, their bike shop closed for good during the pandemic. (Hint: business idea for the mechanically inclined and winter resilient!) So my ride was in jeopardy.

A bike on a do-it-yourself bike repair stand in Grand Marais.
Grand Marais has impressive bike infrastructure for a town its size … but not a bike mechanic.

Lesson: Be ready to improvise, and to forgive yourself.

Warning: Trust your bike, but even then it can fail you. Have tools to fix things, but recognize that no one is fixing a crank on the road.

Highlight: Gitchi-Gami is still a great trail, and Grand Marais is a great place to have a problem, all told.

Featured Trail: Gitchi-Gami State Trail.

Day 7: Grand Marais to the Canadian border. 41 Miles

Strava map showing the route from Grand Marais to the Canadian border.

With hindsight, I got lucky, having technical difficulties so close to the end. Our mother met my brother and me in Grand Marais, to bid my brother off on his Superior-circling endeavor. She brought with her a folding bicycle she had chanced into, thinking she might ride with us along to Grand Marais if things worked out. That meant there was a bicycle for me to use for the last 40 miles between Grand Marais and the Canadian border. And I was going to ride it on a dinky folding bicycle that I learned to ride in downtown Grand Marais.

The author on a folding bike — and his brother on a road bike — on a path overlooking Lake Superior.
Sometimes you improvise and ride 40 miles on a folding bike.

It was, in a word, exhausting. There’s no more trail beyond Grand Marais. There’s not much beyond Grand Marais, period. But it is extravagantly beautiful. Sparse.The highway shoulder edges up against bays of Lake Superior, next to fishing shacks, decades past habitability, falling into the cold lake. The Ontario license plates begin to match the Minnesota plates in number.

Six miles from the border, you come to the Grand Portage National Monument, which is next door to the Grand Portage Lodge & Casino, which has an expansive gas station. It’s the best (basically the only) place to stop before you come to Mount Josephine, a huge ridge that you realize is the final (physical) obstacle between you and Canada. It’s basically two miles of riding uphill. The shoulder is wide, but the slope is constant.

Warning: You feel as though you’re heading into the great unknown, and you are.

Highlight: The coast is worth the climb (Mount Josephine)

Featured Trail: None of those here.

It’s Over, But I Could Have Kept Going

You get to the top, eventually. You crest the peak and begin to coast. Past steep rock walls on each side, there’s an inland lake to one side. You coast farther, gaining speed, perhaps a lot of speed if you’re really weighed down, and then there’s the big lake, framed by Pigeon Point and the sharp rocks of the Canadian Shield. And you look where you’re going and realize that ahead, in the middle distance, is Canada — that you made it.

The author kicking out his legs from his folding bike on the way down Mount Josephine.
The author celebrates on the descent down Mount Josephine.

If you’re me, it means the trip is almost over. You can try to absorb it to memory: the sun, the cool air, the smell of warm pine. You could make it imperative as a once-in-a-lifetime experience. But coming down that hill, I only became resolved that it wouldn’t be once in a lifetime. I resolved to come back — to ride the slopes of Mount Josephine, but more than that. Maybe more than the entire way we had come.

We rolled into Grand Portage State Park, which doubles as the Welcome to Minnesota rest area. We took a picture (below) posing on the “Minnesota Welcomes You” sign. No traffic passed while we did that, so I think we got away with it. I took a view of the Pigeon River, Minnesota’s northern border. We ate lunch, my brother, mother and I. My brother steeled himself for his longer, crazier ambition — and his goal to reach Thunder Bay, Ontario, 36 miles more, by nightfall. My mother and I got to relax, while I began to feel a strange resistance to returning to real life.

I haven’t been off my bike all that long. I’m still figuring out how this trip changed me. My brother and I have noticed, and joked, that the enlarged muscles in our thighs (our quadriceps, I’ve since learned) now make it look as though we have second kneecaps. Driving back to the Twin Cities with my mother, during the endless June day, I saw the road signs for the towns we passed through, or the very shoulders and trails we were riding on. I remembered the feeling of some of the places — and have totally lost others in the hypnotic rotation of the pedals.

Temperamentally, I’m often the person ready to return home from a trip or vacation. But less so this time. I know I could just … keep going. In a very real way, I want to keep going. Life continues — and I have lessons and memories and dreams to carry with me to next time. As well as some stuff that I need to pack onto a bicycle frame. 

The author and his brother pose triumphantly by the "Minnesota Welcomes You" sign at the Canadian border.
Celebrating at the Minnesota-Canada border.

Prodded to reflect, I’d offer that Minnesota absolutely has urban-rural divides. But I’ll also offer that the divide isn’t so large that you can’t cross it on a bicycle, that the climb isn’t so far that you can’t make it to see the other side. If you’re up to it, I can only encourage you to do it. To dream it, to do it, and then to dream it again.

Max Singer

About Max Singer

Max Singer is Minneapolis born, raised, and returned. He's had a lot of odd jobs and wacky experiences for being Gen-Z. Max gets around- at times by foot, bicycle, light rail, bus, car, boat, delivery van, train, and sometimes, escalator.