While walking the dog through our village one brisk November morning, I came across a woman bundled in winter gear, quietly watching her husband back a massive transport truck into her daughter’s laneway. Hitched behind the cab wasn’t just a trailer—it was their new home.

The trailer was extremely large. And as I got a closer look at the rig, I noticed that between the trailer and the cab of the truck was a little Smart Car – those little Mercedes’ cars that are unfortunately no longer available here in Canada. It was sitting above the hitch plate of the truck behind the cab.

The hitch plate is normally where you connect a transport trailer to a truck cab unit. You often see them on fifth-wheel camper trailers, but this one was different because the camper trailer was not sitting on the seat of that hitch plate, rather it was connected by a hitch behind the rear wheels of the cab of the truck. These folks had built a custom platform over the hitch plate and the Smart Car was sitting on it, belted on. I imagine that they could take the car off by driving over some ramps like they use for loading and unloading ATV’s or snowmobiles here in the rural areas. (Everyone seems to have an ATV, or a side-by-side here. Snowmobiles are everywhere).

That hitch plate arrangement was definitely unique, though!

As I continued walking and gawking at this “road-ready” arrangement, I’d worked my way up to the lady who was standing there on the street. I asked her: “Are you getting ready to go camping”. “No”, she said, “We just sold our house and we bought this trailer. This is now our new home. We’re parking here in the driveway of my daughter’s house and will be staying here for the rest of the winter while we plan what we’re going to do in the future with our trailer home”.

As this was now early November, I couldn’t imagine getting ready to live there in a trailer for a cold Canadian winter. Silly me, I didn’t ask her if she planned to live in the trailer during the winter, or in her daughter’s house.

Their story got me thinking—not just about the logistics of trailer living, but about the deeper motivations behind it.As there is very little to keep the mind busy when walking the dog, I asked myself the great philosophical question: “Is this a bold reinvention of retirement or is this some romanticized escape to gloss over the real challenges of getting older?”

From personal experience, I know a few things about what older folks think about when aging, particularly those of the baby boomer generation, like me. Folks like us are at the stage where mortgages have likely been (finally) paid off. Many think that their house is their pension plan, so somehow they believe its time to convert it to cash. House rich, cash poor applies to many seniors. With housing costs rising, it may seem like a good time to sell and somehow to use that cash to live comfortably in the retirement years. And to “downsize”.

While seniors struggle with the physical challenges of getting older, “downsizing” is a critical emotional time when you get rid of many of the treasured articles that you’ve accumulated through most of your life. (They are now, unfortunately, worth very little to sell, and even less as desired inheritances for your children).

Old downsizing-boomers are often looking for a way to live in smaller homes, usually more mobility-friendly bungalows, with less maintenance and potentially lower taxes. Some people avoid this step and actually move directly into retirement homes, which is an even smaller version of the “retirement bungalow”. That lifestyle lets someone do the cooking and maintenance for them, but still allows relatives to visit (without staying over). It also offers less responsibility to be the host for extended family get-togethers.

Perhaps more so today than in the past, older people in the throes of retirement, seem to like the opportunity to travel, not just to visit relatives, but also to go to warmer or more interesting locations internationally. These older retirees find a certain appeal in this kind of mobility, but confusing airports and long aircraft flights may keep them from undertaking this type of travel. Enter the growth in “freedom on the road” travellers, those pulling hotel-RVs behind them.

I know several older folk who have had this desire for a road travel adventure. It’s the chance to see places and do things that maybe they didn’t have an opportunity to enjoy when they were younger, and were raising a family. Indeed that opportunity may have been foregone during the child-rearing times to ensure that the mortgage would be paid off. Now, with the chance to travel, there must be a certain allure with trading in permanence for the possibility of adventure – a “do it before you can’t” opportunity.

Certainly driving for many miles, even within this vast country, is the chance to experience a great adventure. The lady on our local street with the new trailer-home had such a happy, contented look on her face. I’m sure that adventure idea was what was going through her head. I sensed, it was the beginning of a new life for her and her husband. Who knows what her adult years involved in terms of challenges? This could now represent the most exciting new stage in their mutual life experience.

In a rural area, such as where we live, people may often live on farms for most of their lives.  They work hard, sometimes 24 hours a day, seven days a week, constantly tending to the responsibilities of a family and farm chores. The chance to put that behind, to think only about the next adventure without the responsibilities of the past, must offer a great sense of relief and excitement for the future.

And what are the options that they might be considering after leaving the farm life behind? One of those options could be the retirement home we talked about. It could also be just buying a small home in a small village. My local optometrist tells me that he is seeing this happen more and more in the small town where he works. I’d be very surprised if these new retirees are looking to move to larger communities, although there certainly would be more services available much closer to their new home than on the farm. Of course, that would also mean handling significantly more costs associated with moving and living there, and more adjustment in getting used to the urban lifestyle.

I have noticed as I drive the rural roads in our area that many farm homes have a big trailer sitting at the back of their house. Those who look after crops during the growing and harvesting seasons may have an “off peak” period of time during the winter when they “escape” in those trailers. (Those who tend livestock may unfortunately not). Maybe some are the snowbirds that we often hear about that end up in Florida for the winter. These folks are particularly comfortable with living in a trailer, I’m sure. So for them, downsizing to a very large trailer – and I must admit this lady’s was a very large trailer- may be more comfortable and adaptable for those living in rural areas because of the familiarity with trailers.

The woman did indicate to me that there were many things she wanted to see. But she and her husband were in no hurry to get anywhere, she admitted. In travelling, she just wanted to take it all in.

I wonder if that couple had done an extensive analysis of their new future. She did indicate to me that when the offer came in for their home there was a requirement to move out very quickly. I’ve experienced that pressure and it doesn’t allow much time to do anything except complete the legal and financials, and “get rid of stuff”. Who knows how much forward thinking they did on this matter, other than to consider the next step as an adventure.

So let’s just look at some of the pros and cons of seniors selling the house and living in a big trailer, travelling at whim all over the country.

On the plus side, they have the freedom to roam. They can explore new places and don’t have hotel costs or fixed schedules. They can simply “go where you wanna go”. Those people who live in a trailer don’t pay any property taxes. There are no utilities to pay except perhaps telephone, which may not be a significant new expense. The “downsizing” need certainly encourages folks to declutter – big time- and to embrace a comfortable, but minimalist, lifestyle. Many people who take up the “freedom on the road” life find others with similar interests, and so RV parks and travel forums can help foster new friendships and new relationships that are interesting and rewarding. The other thing about the new life is that the travellers can follow the weather. If the weather is good they can go somewhere, or stay and enjoy it. If the weather is bad, they can hit the road to change locales, stay put, or even visit family. They can do the latter without inconveniencing them because they’ve got their house on wheels. They can change their plans easily, just as this lady had indicated, so there are some really good, state-of-the-mind pros.

But what are some of the cons? Certainly in Canada, winter is a huge challenge, particularly if living in a trailer. Heating or lack of insulation can make it cold. As well, the need for water and sewage system hookups can be problematic. If you go to an RV park, there may be incremental charges for some of those things, or worse they may not be available year round. But within Canada, you may be safe to live during the winter on the west coast where freeze-ups are less likely.

Even with new rigs, there may be maintenance demands, both for the truck and the trailer. There will not be the local mechanic to rely on, or a garage to work on for repairs that might easily have been done before at home. Certainly living in a limited space can strain relationships, too. I know of several retired folks who found when they retired that living together was a lot more difficult than when they were working separately.

In Canada, access to healthcare is a problem. It’s difficult to get a doctor in any respect, but to require a doctor when you’re travelling may be extremely difficult. There is provincial coverage for Medicare, but residential permanence is necessary, so as you cross the country, things can get complicated (not to mention for income tax filing too). If a serious medical problem arises, you may suddenly have to find a solution for changing drivers, or worse, for quickly selling the rig. These are not easy things to cope with, and they seem to be more difficult as you age.

“Freedom on the road” brings a whole new world of financial and emotional unpredictability. Certainly, fuel costs will be higher. High repair costs may be something you’re not prepared for. And with campground fees, things can add up for all those little “extras”. There is also an emotional toll when you leave behind familiar family, routines, neighbours, and community ties. Emotional adaptability can be a challenge.

As I look back on this smiling woman, I’m wondering if she had done detailed pros and cons, would she still feel as confident about what she’s doing. Is this really the beginning of something brave, or is this a colossal folly? It would be valuable to hear and share experiences of people like her who have done this.

Why? Because, I think, at the back of every retiring boomer’s head, is that same desire to get away and do something exciting like “freedom on the road” in their senior years.