Planes, Trains, and Automobiles: Making a Run for the Border in Windsor

Air Canada, Trip Reports

My time in Canada was over, and I figured getting back into the US wouldn’t be hard. I was most definitely wrong.

I knew I had to rent a car once in the US, and my last stop would be Chicago, so I took a look at what it would be like to just get a car from there. Then I could fly Porter over… but the car was surprisingly expensive. So, I just started looking at one way rentals from various points in the US. Of everything I saw, a Detroit pickup with a drop off in Chicago was by far the cheapest at under $500 all-in for 9 days. That seemed like it would be simple enough.

I could have flown from Toronto, of course, but the idea of shelling out around $450 for the 200-mile flight was just too distasteful. I had nothing but time, so why not make it a multi-modal adventure?

The first part was easy. I bought a ticket on Via Rail on the early morning train to Windsor for C$64. The station was just a couple blocks from the Marriott, so I wandered over in the already warm morning air and into the main hall.

The boarding areas were full of people going to Windsor, Ottawa, and Montreal, and elsewhere. I lined up in my group and waited.

On the train from Quebec City to Montreal, I was in business class which was 1-2 across. This time, I was in deepest coach which was 2-2 across. The seats were still very comfortable, I had ample legroom, and there was power available. Wifi was theoretically offered, but it was very slow. That was a shame because I needed to figure out how to get across the river into Detroit.

Between Windsor and Detroit, there is the nearly 100-year old Ambassador Bridge and the 90+ year-old Detroit-Windsor Tunnel. Those are the two choices unless you have a boat or you wait until the long-delayed Gordie Howe International Bridge opens in 2024… or whenever it actually gets done.

Since these two routes across the river are terribly undersized for today’s traffic, the only option to cross is in a car. There used to be a public bus you could take but the pandemic killed that. Don’t even think about walking, biking, skating, or gallavanting across until the new bridge opens.

This left me in a pickle. I called Tourism Windsor Essex Pelee Island — that is actually the mouthful of a name of the local visitors bureau — which gave me nothing except to say that a cab might work. It would be at least C$100 but it would depend upon the traffic at the border, because the entire trip would be metered. Oof. Uber was maybe an option too, but it all seemed very unclear.

As I plotted my path, I was only occasionally distracted by the absurdity of the Falcons-attired neighbor across the way. He was loud, so I learned quickly that he was actually from Canada and not Atlanta. He was mad that the train was late (by only a few minutes), and he was told multiple times to put his mask on properly. He did not care.

In between all of this, I reached out to the Twitterverse for help on crossing the border. There were ideas, including one person who offered to ask his friends if they could drive me. (He did. They couldn’t.) I spoke with the service director onboard, and he gave me the number of the cab company I already had.

We pulled into Windsor maybe 20 minutes late in the shadow of the Hiram Walker Distillery, still with no clear plan. My mind instantly drifted to whiskey, but then I snapped myself back toward the task at hand.

I marched up to the Via Rail ticket counter and a very bubbly and welcoming young lady told me that she gets this question every day and remains truly frustrated that the bus hasn’t returned. I get the feeling her version of “truly frustrated” is me on a happy day.

She told me that a cab would probably cost C$100 to C$120, but I had to find a cab driver with a passport since not all of them had one. She also passed me an often-copied piece of paper that just said “airport shuttle” on it with a phone number. Sometimes, she’d said, people had luck with that even though no airport was actually involved.

I called the number, and a friendly woman who sounded like she’d smoked a lot in her day answered the phone. I told her what I needed, and she said she could be there in 15 minutes in her Jeep Cherokee. It would be C$70, a flat rate. Done deal.

Sure enough, just a few minutes later her dog hair-covered SUV arrived. She told me to sit up front since there was less hair up there, and we were off. The drive to the tunnel was filled with conversation ranging from rising homeless and drugs in Windsor to how Arabic-owned businesses could be identified by having lights around their doors. (I have no idea how true any of that was.) She also told me how she was a convicted felon. (She admitted it was just an arrest for growing pot in the ’80s, but it sounded better the other way.)

We made a stop on the way to the tunnel to buy a carton of cigarettes for her friend. That seemed reasonable enough to me; I had nowhere to be until later on and this just added to the story. In the duty-free shop, I picked up a bottle of Wayne Gretzky wine for my friends that I hoped to eventually reach that evening.

Into the tunnel we went, darting by the flags that marked the actual border.

The line into the US on the other side was only about 5 cars deep, and the immigration officer looked at my passport and waved us through without any questions. We popped out at the base of GM’s headquarters with me celebrating finally being back on American soil.

I thanked my new friend, and she drove back home while I figured out my next move. I went over to the river and walked by Hart Plaza. The place was all quiet on a weekday. I had expected at least a little more action, especially since it was lunch time. But no. So I decided to move on.

My plan was to take the Smart-Fast Bus to the airport. FAST stands for frequent, affordable, safe transit. I’m sure it will not surprise you in the least to hear that not all of those guarantees were met. It was cheap at only $2, and yes, it was transit. Was it safe? Well, we made it. But it sure felt like the bus was going to fall apart on some of those under-maintained roads. And it was not frequent.

Google Maps had one schedule but specifically noted that this wasn’t the most recent timetable. I walked to the stop at the corner of Jefferson and Beaubien and found a beat up sign showing the schedule, which did differ from what Google had.

Buried in the conga line of signs was a note that I could text my stop number to get estimated arrival times. You can probably imagine how that worked out, but just in case you can’t, here’s the screenshot.

While I waited, I tried to buy a ticket online, because I didn’t have exact change. I set up an account and got to the last page when it told me it would be $2 plus… $2 shipping? Were they going to mail me an actual paper ticket? This was a bad idea, so I bailed out and hoped I could use a card on the bus.

The bus arrived at a time that did not match Google or the sign, so whether it was on a schedule or not was entirely unclear. I asked the driver if I could pay with a card. No. Did she have change? No. Was there anything I could do? No. When’s the next bus? I don’t know. Door closed. Welcome to Detroit.

My next plan was to find a place to eat and get change since the sign suggested the buses ran every half an hour. I walked back over to the GM building and the signs all over said it was closed. An officer with a bomb-sniffing dog walked by and said otherwise. He said to try the doors in a friendly tone, so I did — hoping he wasn’t just looking for a fun way to spend his afternoon booking me for breaking and entering — and they opened. I walked in and found the food court which was a sad scene in its own right.

In the shadow of a whole bunch of nice-looking cars, new and old, (above) was the mostly empty, poorly-lit food court. The healthier option of Subway was closed, so I settled for a very bad gyro from Coney Dog. But at least I had my $2 in exact change.

I walked back out to the bus and waited. And waited. And waited. Did I mention it was not frequent? The bus did eventually arrive, again not at a time on the sign or in Google Maps, and started to wind its away around the city, stopping seemingly at every corner.

This was also not FAST, taking over an hour to weave through construction, make illegal u-turns, and even miss a couple stops that people had requested.

The entire ride was filled with characters, including a woman across the aisle talking to anyone who was near her. Her longest conversation was with a guy who, I later learned, used to work for Northwest. She had all kinds of theories for him ranging from when to buy plane tickets (Tuesday or Wednesday) to her 9/11 theories (it was an inside job, of course). I later learned she was taking this hourlong bouncing bus ride to go buy a ticket on Spirit to save the online ticketing fee.

We finally arrived at the airport, and I made my way down to the ground transportation area only to find that I needed to take another bus back out to the rental car area. This time, I was booked at Dollar which is in a corner of the Hertz lot.

My streak of meeting strange people continued. On this bus, the woman across the way asked the person next to her a question. That opened the door for her to begin bragging about all kinds of things. She had published an article that was read by over 1.5 million people. The author of some TV show had retweeted her. The people next to her seemed genuinely interested. I just wanted off the bus, but that would have to wait because the good people of the Detroit airport decided to close two of the three lanes exiting the terminal for road work. And there we sat.

Once I arrived, Dollar proved why it was cheaper. There were plenty of Hertz counters with no line, but Dollar had two — well, one and a half — agents slowly checking people in. I crawled my way to the front of the line, got the key, and then 3 hours later I was in a small town in central Michigan eating dinner and drinking a beer while looking out at a lake.

It was a very long day, but it was quite the adventure. After 3 nights at the lake, I came back to see a Tigers game (that’s a great ballpark), drove down to visit a friend in Columbus for the night, and then headed to my in-laws to re-unite with my wife and kids in Indianapolis. We drove up to Chicago to see her brother and his family, and then it was time to head home.

The final post in this series will document that adventure. Why? Because it wasn’t on airplane but rather a scenic ride on the rails with Amtrak’s Southwest Chief.

Planes, Trains, and Automobiles posts so far:

12 comments on “Planes, Trains, and Automobiles: Making a Run for the Border in Windsor

  1. What a schmozzle to get across to Detroit! Flair launched flights to Windsor from Halifax which got me thinking about hoping over to Windsor, grabbing a burger at the Lumberjack and catching a Tigers game. The idea of a taxi across seemed like an awkward way to go (which was proven in your story), so maybe this will be a realistic journey when the Windsor Transit bus (Hopefully) comes back.
    Detroit may not be the dream destination, but it has a very handsome skyline, and the walk along the river on the Windsor side does provide some beautiful views.
    Enjoying following the journey!

    1. Hehe, the one thing I remember about walking along the river on the Windsor side is seeing the “United States Postal Service” painted on a processing center, high enough and with big enough letters that the only people who could regularly read it were in Canada.. Seemed like such an odd thing.

  2. As a consultant, I worked for a time at the Renaissance Centre (now HQ of GM). From Toronto, I used to fly down to Windsor, get a taxi to the tunnel, and then the bus over. When I first started, I had gotten a few taxis to take me over, but only had about 50% success in getting one to agree before just settling on always using the bus. The bus was very easy, and nicely had a stop right outside the tunnel which provided easy access to the Ren Cen. Looks like on the Transit Windsor website they say the bus will return on Sunday, November 27th.

  3. DTW is in an interesting location, as it’s not as close to Detroit or the Canadian border as one might think; it’s well southwest of Detroit proper and (both as the crow flies and as the highways curve) is basically equidistant between Ann Arbor (University of Michigan) and downtown Detroit. I’d argue that that’s actually a net benefit for the airport, as it makes DTW much more convenient for the broader geographical region (it’s common for people in the Lansing metro area to fly out of DTW instead of LAN, for example).

    On a slightly different note… With some exceptions (SFO and ORD come to mind), I feel like most of the mass transit connections to airports in the US primarily serve airport workers and often aren’t quite super convenient for arriving and departing airport passengers. That’s certainly been the case in my experience at airports like LGA, ATL, etc.

  4. Forgot to add…

    Cranky, the next time you’re in the Detroit/Michigan area, the Yankee Air Museum in Ypsi isn’t far from DTW and is well worth a visit. You can literally stick your head in the bomb bays of a few restored WWII-era bombers (not many “velvet ropes” there, unless it’s changed in recent years), and even fly in one as a passenger for the right price.

  5. Thanks for the great story telling that manages to weave in all kinds of travel lessons.

    Best line: My mind instantly drifted to whiskey, but then I snapped myself back toward the task at hand.

  6. It’s so funny you mention Dollar at DTW – I had a similar, awful experience two weekends ago. The entire car rental experience took almost 2 hours.

    We waited about 30 mins for the shuttle to the car rental facility then once it dropped us off there were 3 people in front of us…and we waited….and we waited…until it was our turn, took about 15 mins from one of the 1.5 agents (there were 4 employees ‘present’) to get us processed. We proceeded to a spot number, and were instructed to take only that car at that spot. Well, there was no car at that spot. I returned to the building where I went up to one of the “workers” who made eye contact with me as I cut the line (no way I was waiting again). I was chastised for not saying “excuse me” by the other 0.5 worker and politely explained there was no car. “That can’t be” they said. Well unless I’m dyslexic, there was no car there or anywhere near that spot. After disgruntled shuffling and groaning we were finally instructed to take a car that had just been cleaned out in front of the building. Ok, but it was a class below ours and at this point, I could accept that. But it was also a quarter tank down on gas – ok – maybe I’ll go inside again…no, we’re already late.

    We made it to the wedding….late. Thanks Dollar DTW!!!

  7. CF – let me know when you start writing travelogues! I really do enjoy your style! And, frankly, a lot of what you do is exactly the sort of thing I would do also! And, I suspect from the positive comments here and on similar work that you have done, I am not alone either!
    Great work – and thanks for these!

  8. WRONG ! To say that “ … these two routes across the river are terribly undersized for today’s traffic” is a widely believed myth. The border delays are the result of underfunded border agencies not the capacity of the bridge or tunnel to handle traffic.

    1. DCamM – I think you’re missing the context. For cars, I didn’t see anything to suggest it was undersized. But there is no way to use any other mode of transport to cross the border, and that’s where these are undersized. There’s no room.

  9. I’ll take crossing the border from Windsor to Detroit over crossing from Emerson, Canada to I-29 in North Dakota. I got pulled over to have my rental car searched every. single. time.

    I guess an American driving to and back from Winnipeg is just too darn suspicious.

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Cranky Flier