We shall not cease from exploration
And the end of all our exploring
Will be to arrive where we started
And know the place for the first time.

T. S. Eliot, “Little Gidding” from Four Quartets

I do not, generally, enjoy backtracking. It feels too much like wasted time to travel the same track twice, especially when the medium of that travel is as slow and unreliable as a small, engineless sailboat. Far more satisfying to let your journey scribe a wandering circle on the map, one that permits aimless meandering and deviation, but in the end (and without the need to re-trace any of the route you’ve already sailed) brings you back to your starting point wiser, and more experienced. With a better tan. That’s why, among cruising sailors, those who have completed a circumnavigation rank highest in the pantheon.

But setting out across the open sea in a small open boat is a daunting prospect - too daunting, these days, even for my dreams. Usually. Webb Chiles has done it (or nearly so), as has Anthony Stewart, and you can read about their journeys HERE (Webb Chiles) and HERE (Anthony Stewart). So maybe someday I’ll head offshore myself, and just keep going until I’ve gone right round. Probably if I do, though, it won’t be in an open boat. Maybe something a bit more like THIS would be the ticket.

Still, something of the satisfactions of the circumnavigation can be found even in local waters suitable for the smallest boats: a trip around a favorite island, a coastal circumnavigation of a lake or bay - or perhaps, something a bit more ambitious, like this month’s imaginary voyage.

“What we call the beginning is often the end,” poet T. S. Eliot writes in “Little Gidding.” “And to make an end is to make a beginning. The end is where we start from.”

So. The end is where we start from - my own doorstep, or at least as near as I can get to it. A backyard circumnavigation. It’s a trip I’ve been mulling over for a couple of years now, which means (I suppose) that I’ll actually do it sometime. Of course, the route I describe here won’t be a “backyard” route for most of you, but maybe it’ll inspire your own explorations. If you’re too landlocked to find a similar opportunity, remember that a small boat goes to windward at 60 mph once it’s on the trailer. Maybe some of you will beat me to this one.

What makes this idea work is that Wisconsin is tucked into an elbow of the Great Lakes, bordered on the north and the east by navigable waters. And on the west, the Mississippi and St. Croix rivers. Add in a relatively short upriver jaunt along the Rock River, and a couple of portages, and a complete circumnavigation of the state becomes possible - not bad for a Midwestern state more than 1,000 miles from salt water! Here’s the idea (the route is marked in red):

And a little bit closer look:

I don’t live near the state’s border, but I do live 8 blocks from the Chippewa River, which flows into the Mississippi 60 miles downstream. I’ll need to drive about 15 miles south to get past the lowest dam before launching, and then I’ll be off on my backyard circumnavigation.

Leg 1: Eau Claire to the Mississippi River via the Chippewa River (60 miles)

The thing about quiet Midwestern rivers like the Chippewa is that they let you sneak through the world along the crooked corners and thin slices of undeveloped land that still remain hidden away between the towns and farms, secret pathways available to anyone who can get a boat into the water. A river trip is like sneaking along backstage, getting a look at what’s really going on while the world shows a different face to people passing by in cars.

Sunset on the Chippewa River

Done right, no one will ever know you’re there. But doing it right means having a boat that will let you sleep aboard at anchor or nosed up onto a beach (more on the boat later). Ask for forgiveness (if you have to), not permission. There’s almost always a quiet corner to pull into where you can pass the night undisturbed.

Leg 2: Mississippi River to Rock River at Davenport, Iowa (280 miles)

Next comes the Mississippi, a river with a mythology and an aesthetic all its own. It’s a river that must haunt the dreams of everyone who’s ever held a paddle or hoisted a sail, an emblem of freedom that runs through both the geographical and metaphorical centers of the nation. What boatman can hear the river’s name without being swept along in a current of possibilities?

“It is a strange study - ” Mark Twain (who knew the river better than most) told his friend Will Bowen, “a singular phenomenon, if you please, that the only real, independent & genuine gentlemen in the world go quietly up and down the Mississippi river, asking no homage of any one, seeking no popularity, no notoriety, & not caring a damn whether school keeps or not.”

Indeed. That’s what the Mississippi will bring, for 280 miles, as we work our way southward into Illinois - wide channels, wing dams and locks, quiet backwaters and marshes, and the steady traffic of barge streams heading upriver to Minneapolis, or downstream to Cairo and Louisville and beyond. I’ve had a little chance to explore some of it already (earning no popularity, no notoriety, and not caring a damn about much of anything other than whether I’d be able to find my way back to the car and trailer):

On a couple of overnight trips close to home:

Where we snuck through some tangled channels and deep into the side marshes:

Getting mostly, if not quite irreversibly lost:

But the chance to sail a long segment of the big river, stopping off at various river towns along the way, is something I’ll really enjoy. Come ashore from a boat and you’re a traveler, not a tourist. There’s no better way to travel. With a steady (if sluggish) current in our favor, we’ll hit Davenport and the Rock River in ten days, maybe. So, two weeks into our trip.

Leg 3: Davenport, Iowa to Beloit, Wisconsin (155 miles)

The next leg of the journey takes us up the Rock River and into southern Wisconsin. The Midwest is a land of small rivers and small towns, and an intricate network of rivers like the Rock snake their way through the geometrical progression of squared-off cornfields as if trying to slip backwards in time. There’s nothing exciting, maybe, about a journey along a quiet small-town river, but it’s immensely satisfying just the same, an exploration of a landscape that shares its space with the people that live along its banks:

The Rock River farther north, in Ft. Atkinson, Wisconsin

Reading the names of the river towns along the way is like reading an account of a not-too-distant past that (just maybe) we ought not to have left so far behind: Prophetstown, Lyndon, Sterling, Dixon, Byron - quiet pragmatic Midwestern names. Maybe we’ll stop at a riverside Dairy Queen for a hot fudge sundae, or catch a softball game at a town park. Then it’s back to the boat for another night aboard, hidden away in some niche of the river that can’t be discovered by land.

It’s upstream, of course, which means we’ll need a boat that moves along easily under oars. More on the boat later.

Leg 4: Beloit, Wisconsin to Kenosha, Wisconsin (Portage #1): 70 miles

And here’s the first hitch, a 70-mile portage from the Rock River and into Lake Michigan. We could work our way closer to the lake by staying on the river longer, maybe, but there’s a nice series of quiet back roads that run right along the Wisconsin-Illinois border, making a true circumnavigation possible.

The trick, of course, is that we’ll need a way to get the boat there. Easy enough, I suppose, to call a friend to fetch my trailer - but that seems to run counter to the spirit of the endeavor. Instead, I’d opt to use a boat that can be pulled easily by a bicycle (a trick that distance rower Colin Angus and his wife used on their journey from Scotland to Syria) - and can carry the bicycle and trailer aboard when underway.

That’s why I think something like THIS would be perfect.

You can see this design in action in the video below. It’ll need a sailing rig (I’m too lazy to row the whole circumnavigation), and maybe some slight modifications to allow sleeping aboard, but I think it’d do the trick. I suppose that means I’m already thinking of building my next boat…

Leg 6: Kenosha, Wisconsin to Rapid River, Michigan: 260 miles
And then we’re in the big bad lake. Not much shelter on the Wisconsin shore, especially at the south end, but a cautious skipper and a boat that can be dragged up on land just about anywhere will help make it work. Along the way, we’ll be sailing up the beautiful eastern shores of the Door County peninsula (the thumb of Wisconsin) and may just have to make a stop in Bailey’s Harbor, where there’s a nice independent book shop and lots of restaurants. It’d probably be foolish to sail past Door County without taking in a fish boil at least (I’ll steer clear of the lutefisk, though).

Leg 7: Rapid River, Michigan to Munising, Michigan (Portage #2): 35 miles

And another portage, this one right across the narrowest neck of Michigan’s Upper Peninsula and on into Lake Superior. The nice thing about fresh water sailing is that, no matter how wet my bicycle and bike trailer have gotten on the journey up Lake Michigan, it won’t be too rusty to work. A one-day bike trek across the UP and it’ll be time for:

Leg 8: Munising, Michigan to Superior, Wisconsin: 350 miles

Again, big waters for a small boat. We’ll be launching right at Grand Island, where I’ve done some sailing before:

We’ll be right at the western edge of Pictured Rocks National Lakeshore:

And then we’ll head westward along the southern shore of Lake Superior, cutting through the Keweenaw Waterway to avoid a long, exposed trip around the tip of the Keweenaw Peninsula:

And on through the Apostle Islands, where I’ve sailed before.

This leg of the trip will be a bit exposed, but with caution - easily possible. At the end we’ll sail into the harbor at Superior (dodging the 1,000-foot ore boats) and up the St. Louis River to a boat landing near the Oliver Town Hall.

Leg 9: Oliver Town Hall to Gordon Dam (Portage #3): 40 miles

Another bike leg - the last one.

Leg 10: Gordon Dam to the Chippewa River: 200 miles

Another quiet river journey, after a few hundred miles of sailing on the big lakes. We’ll be starting at Gordon Dam, at the upper end of the St. Croix River. This will be a bit more of a wilderness segment than the Rock River, along a National Scenic Riverway, with some minor ripples and rapids. Beautiful northwoods terrain, and all the time getting closer to home again.

It’ll be a fitting way to end the trip - on river time, winding down to a slow stop, a gradual routine to shorebound life, with its obligations and routines and relative immobility. Still, after almost 1,500 miles (and 90% of that by water - not bad for the landlocked Midwest), it’ll be time to set down in one place again for a while and let the world move on without me. I’ll probably pull ashore in Wabasha (Minnesota) and skip the upstream return along the Chippewa. I’ll have been gone three months or more, maybe. My wife will probably agree to come and pick me up by then.

And that’s the beauty of a circumnavigation - it brings you back to where you started, just when you’re ready to be there again. To settle down at home, and know the place - and ourselves - for the first time again. I can’t think of a better reason for a small boat journey.

TOM PAMPERIN (www.tompamperin.com) is a freelance writer and small boat sailor, and (under protest, sometimes) even a boat builder from time to time. He lives in northwestern Wisconsin with his wife and cat, who are decidedly NOT sailors.

Tom’s first book, Jagular Goes Everywhere: (mis)Adventures in a $300 Sailboat, is available from Duckworks HERE.