Thanks to an Amtrak employee acquaintance who provided some advice for this trip.
As I never get tired of saying, one of the best things about living in Chicago is that you can take a one-seat passenger rail trip to just about every major city in the U.S. And one thing that's nice about Amtrak is that it's getting easier and easier to bring a bike along on the trip, which opens up a whole universe of possibilities for car-free long-distance travel travel. It's certainly preferable to the ridiculous expenses and hassles often associated with taking a bike on a plane.
Taking a bike on a cross-country train route used to be a major production, which required bringing or buying a bike box, taking tools to the station, removing the pedals and rotating the handlebars 90 degrees to one side and flipping them upside down (plus more dismantling if you were using a smaller container), boxing up the bike, checking it as baggage, and then doing the reverse at your destination. (Routes that exist solely in Illinois, which are state-subsidized, have offered unboxed "roll-on service" for as long as I remember.) But nowadays relatively convenient bikes on Amtrak access is becoming the rule rather than the exception.
I took advantage of that fact for a trip to the tiny town of Seeley, Wisconsin, more like a crossroads, for the 60th birthday party of my old friends married couple Liz Schoone and Dave Schlabowske. Dave has previously worked as the bike and pedestrian coordinator for the city of Milwaukee, and the executive director of the Wisconsin Bike Federation, and we met at a bike planning conference 20 years ago. During the 2000s, we cohosted a bike ride from Chicago to Milwaukee and back in the dead of winter called The Frozen Snot Century. Some years the ride visited Madison as well. To sweeten the deal, entertainment at the birthday party in a roadside bar would be provided by the Chicago-based UK-American country-punk band Waco Brothers, featuring Dave's sibling Dean.
I took the Empire Builder train (which runs between Chicago and Seattle or Portland) to St. Paul, and then biked about 150 miles over two days. While I brought camping gear, the weather was unseasonably cold, near freezing, so I wound up "credit card camping," staying at inexpensive motels along the way. I'm getting too old to bike 75 miles in 35 F weather, pitch a tent, sleep on the ground, pack up the tent, and then do the whole thing over again the next day!
While taking a bike on the Empire Builder is easy, doing it efficiently, with a minimum of stress, is not super-intuitive, so here are some tips. One thing you need to know is that you can only take bikes on and off the train at designated baggage stops. When booking your ticket online, when you see the page "add bike or pet," choose the $20 (each way) bike option. Once you complete the transaction, your bike will have a ticket and so will you.
Show up at Union Station at least 45 minutes before departure. The Empire Builder leaves at 3:15 every day. (Unfortunately there's only one run in each direction per day.) Go to the ticket counter and ask for a bike baggage tag. The agent will want to see your printed ticket or your email from Amtrak. Use the elastic band on the tag to attach it to your handlebar and go to Gate B. You should be able to roll your bike to the front of line of passengers waiting to board – it's in the interest of Amtrak employees to let you do that, so you don't delay the train while taking you bike to the appropriate car.
Once you're allowed on the platform, ask an Amtrak worker which coach car you'll be riding in, based on your destination. Free-lock your bike and drop off your luggage in that car.
Next roll your cycle to the car the employees tell you to take it to, most likely the baggage car. Assuming that's the case, wait there for an employee on board the baggage car to reach down for you to hand the bike up to them. Then hustle back to your coach to enjoy the ride.
I won't do a full travelogue of my trip (see my Twitter thread if you want that), but here's a gallery with a few of the highlights.
Waco Brothers perform "Northwoods" at Dave and Liz's birthday party, with Dean, second from right, singing lead.
"I was born, foot in my mouth
I was born, a little too far south
Maybe we could steer off course for good
In the Northwoods."
Read the full Twitter thread about my trip to the Northwoods and back here.
And here's a writeup of a car-free, bike-free backpacking trip I did years ago in Glacier National Park via the Empire Builder.