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  • Writer's pictureJim Martin

It Was All Going So Well...

Updated: Nov 30, 2023

I had only two problems left to solve:

  1. Find a place to store the Tiny House until we closed on our new home in Vermont.

  2. Learn how to pull a 20' trailer with a house on it--or really any trailer at all. (And also, what kind of truck does one need to pull to pull a Tiny House 500+ miles up interstate 95).

We needed somewhere to store the Tiny House because the sale on our Virginia house required us to vacate on December 11th and we weren't scheduled to take possession of our Vermont house until about a week later (or so we thought--more on that soon). So we needed a week or two to get things settled at the new property, then we would move the Tiny House there.

Feeling pretty clever, I called every single self-storage place anywhere near our new home. They usually store things like RV's and boats over the winter. It already being winter, however, every single place was full.

Feeling small-town clever, I called the local library in our new town and asked the research librarian for some ideas. She suggested all the self-storage places I'd just called.

Feeling both tech-savvy and clever, Jenna jumped on the NextDoor app in our new Vermont neighborhood and posted that we were looking for a place to store the Tiny House. Within a few hours we were contacted by a guy named Eric who not only lived in the same town in Vermont, but on the same street. Seriously. He lived a quarter of a mile from our new house. Eric was like, "Sure! You can store your tiny house in my driveway for a couple of weeks!" We agreed to rent 20 feet of his driveway for a small fee each week, and our first problem was solved!

It was all going so well.

To solve the second problem, I decided on the phone-a-friend option. My first (and only) call was to my old friend Romie. He does tree work. Specifically, Romie drives a 70 ton crane every day. I figured he'd know stuff. Plus, he's a great guy and we hadn't spoken in years. I was looking forward to catching up.

Here's how the truck part of the call went:

Jim: So I need to tow my tiny house from Virginia to Vermont.

Romie: uh huh

Jim: Yep, I've never pulled a trailer before and I have no idea what kind of truck I need.

Romie: Do you know how much the trailer weighs?

Jim: Uh... I can probably figure it out

Romie: Do you think it's more than 7,000 pounds?

Jim: Holy smokes, I hope not!

Romie: As long as it's not over 3.5 tons, a 2500 should do it.

Jim: A what?

Romie: Like an F250

Jim: uh huh

Romie: A pickup

Jim: well yeah, obviously

It went on like this for a while. Finally I understood I needed a somewhat heavier duty pickup than your average F150 or 1500.

After some more fun conversation, Romie wished me luck and I immediately started looking for a 2500 I could rent one way from VA to VT. After a bunch of web research and even more phone calls, It turns out rental companies generally don't rent pickups one way over that kind of distance.

So, back to YouTube university where the Tiny House community came through yet again. The hot tip was that 20 foot U-Haul trucks are built on a 2500 truck chassis, AND they have a 2" trailer receiver and full trailer hookups! Now, a 20' truck hauling a 20' trailer did not seem to be the most nimble rig, but at least it was an option.

All this research took a couple of days. In the middle of it all, Romie called me back.

Romie: Hey Jim, I was talking to my wife Sarah about you pulling your tiny house to up to Vermont. She said, "Why don't you just fly down there and tow it for him?"

Jim: Seriously?!?

[God bless you, Sarah!]

Romie: Sure!

Jim: That would be amazing!!! Here's the thing though, I can't find a one way 2500 to rent. [See how quickly I pick up on the lingo???] The Tiny House blogosphere says to use a 20' U-Haul. So that's a 20' truck pulling a 20' trailer. Are you comfortable with that rig?

Romie: Sure!

[God bless you, Romie!]

That's how Romie won an all expense paid trip to Fredericksburg, VA.


After some back and forth on schedules, we realized we had only one opportunity to get this thing done. Romie would arrive the night of December 3, and we'd drive to Vermont on the 4th, then back to his house in Massachusetts (and he would go to work the next day).

That's why I needed to get the windows and door in on such a tight schedule!

During the day on December 3rd, I went and picked up the 20' U-Haul. With kids moving into and out of college, we've rented a ton of U-Hauls over the last decade or so. Almost all of them have been a great experience. Solid equipment in good shape and not super high mileage.

This is why I was quite surprised when the truck I am assigned is...old. I mean, old. It's not just that it lacks Bluetooth or even a USB or headphone jack, it's high mileage, and it runs kinda rough. And the tires look a little slick--which really matters because it's been raining all day and the first 30 feet of this tiny journey is out the gate we had specially installed to be just the right size and then across a 20' stretch of my neighbor's lawn. We, of course, have permission, to pull the house over the lawn. Chris and Sarah, my neighbors (who have recently moved in) have been great about it. But more on that later.

Bad tires, high mileage, but this is the only 20' truck on the lot and we are out of time. The only way out is through!

Romie finally arrives on the scene about 8 pm. He's flown down after helping his daughter sell Christmas trees all day. We have some dinner, and then he says, "Let's pull the house out of the back yard tonight so that all we have to do tomorrow morning is drive away." Sounds brilliant to me, so we head out to the back yard.

This is the moment of truth. It's dark. And still raining. And I've spent some of the afternoon loading a bunch of things into the truck. Things like some of my larger tools, some boxes, and our bicycles. Because, for crying out loud, if the truck is headed north it doesn't make sense for it to be empty. This will keep moving costs down. It will also make the truck heavier (which I realize later).

With my classic optimism, I swing the big tiny house gate open as Romie pulls the truck around. It's about 9:30 at night. I feel a bit bad that we are running the truck in Chris and Sarah's driveway. But it'll only be a few minutes, I figure.

Thankfully the truck doesn't have one of those hideous back up warning BEEP! BEEP! BEEP! alarms. It just runs a little rough, and smells like it might be leaking a little gas.

What is so hard to appreciate in the video is that Romie is backing the truck over a hill, up into our back yard, through a tiny gate that is juuuuuuust wide enough to allow the truck and the tiny house to exit--theoretically.

I try to be helpful guiding Romie as he backs the truck in. He's pretty amazing. I am less so. On the third try, I finally give him clear enough direction that he lands the ball smack under the hitch. We lower the trailer onto the ball, hook up the chains and the brake cables. And the trailer lights up just like it is supposed to! Amazing!

Romie climbs back in the cab and drops the tired transmission into Drive. And to my joy, relief, and utter amazement (though I should not be amazed), the entire rig: truck, trailer, and Tiny House begins, gently, to roll forward. The passenger side wheels, which had been sitting in a trench I dug about three years ago climb right out, just like they are supposed to! It's about 9:45 pm at this point--right on schedule. We'll get a good night sleep and start heading north at dawn.

We run into a little trouble when Romie realizes that the line the trailer is following is not quite going to allow the Tiny House to clear the left-hand gate post on the way out.

There are a couple of things to appreciate about this video. The first is Jenna's emotionally-present commentary. The second is my stealthy self stumbling around the back of the house to get a look at how close it is to the fence.

We decide it's a good idea to avoid scraping all the Tyvek off that side of the house, and perhaps damaging the the fence gate at the same time. So, after some discussion, we decide Romie will back the rig up and establish a better line to pull the house out.

I watch the house go back about four feet, then forward again, back and forth, back and forth. But there just isn't enough room to maneuver. After more discussion, we decide we need to unhitch the trailer so Romie can pull the tuck all the way out and back it in at a much better angle. Sounds like a plan.


Pulling the truck out was not a problem, though I do notice that we are starting to compact the sloped grass of Chris and Sarah's lawn pretty significantly. We're going to have to worry about that later. Back and forth goes Romie seeking a better line. And this is were the basically bald truck tires come into play. At some point the wheels start spinning on the slick grass--which is all-too-quickly becoming mud. Romie almost has it lined up and decides to make one more out-and-in maneuver to set up the perfect pull vector. Only... the truck has finally turned enough of the grass into Virginia's particular topsoil alchemy of clay+mud+banana peels.

Now there is just no traction. The truck begins to slew diagonally over Chris and Sarah's lawn. I have a couple of bags of crushed gravel that I break open. I begin throwing handfuls of gravel under the wheels. But all the truck does is slide. The nose of the truck begins angling dangerously close to a beautiful old tree in Chris and Sarah's front yard. Romie throws it in reverse to back away from the tree and the truck refuses. More gravel. Even less traction. It just moves further sideways while the bumper inches closer and closer to treebeard... until it won't move at all. It won't go back. Won't go forward. Stuck. It's not even hooked up to the trailer. And it's stuck.

Jim: Romie... what do we do?!?

Romie: We call a tow truck.

Jim: Seriously?!?

Romie: Sure! He'll just attach a strap to the back wheel and pull the truck sideways to line it up with the driveway.

Jim: [already dialing] Sounds good to me!

At this point some time has gone by. It's about 10:30, and the tow truck is about 30 minutes out. We head into the house to get out of the rain and wait. About 30 minutes later, the tow truck arrives. It's lit up like a Christmas tree and growling like a menacing diesel tiger. I head out back to wave the driver into the right position. He pulls up and throws the tow truck into reverse, and sure enough, BEEP! BEEP! BEEP! as he backs unbelievably slowly into position.

Then comes a painful few minutes of questioning from the tow truck driver.

Driver: What seems to be the trouble?

Jim: Well... we got the U-Haul stuck in the mud while trying to pull the Tiny House out of the back yard.

Driver: I see.

Romie: I think if you pull the rear wheels of the truck just a few feet sideways, we'll be able to pull it up into the neighbor's driveway and and we'll be all set.

Driver: Hmmm [scratches head, walks around truck several times]

Finally the tow truck driver agrees to Romie's plan and starts pulling some equipment out of the various compartments on the back of his

truck: A strap, a heavy duty pully, some connectors. He proceeds to reeve an elegant little bit of rigging that will (if I understood what I was seeing) increase the pulling power of his winch by 50%.

He cranked up the winch. As soon as the slack was taken up, the back of the U-Haul (loaded though it was) began to slide sideways across Chris and Sarah's lawn.

If you are thinking, "That's great Jim, but those tires (bald though they were) must have left a gash in your neighbor's lawn!" That's where you'd be wrong. They didn't leave a gash. What the tires left in their wake was more like a World War I trench.

Undaunted, Romie jumps into the cab of the U-Haul and gingerly pulls it forward into Chris and Sarah's driveway. As I'm paying a rather swinging fee to the tow Truck driver, Romie walks over. In an understated and winsome way, he floats a question:

Romie: Hey, what do you think about backing your four wheel drive rig in there and pulling that trailer out for us?

Tow Truck Driver: [more head scratching and walking around] I don't think so. This truck weighs [I don't remember how many] tons. It would just create a huge trench up in there.

Jim: [looking at the WW1 trench in Chris and Sarah's yard] I think that'd probably be okay at this point.

Tow Truck Driver: I just don't think that's going to work. But, good luck to you both!

At this point it's about midnight and Romie and I decide it's time for radical action. The problem, we now see, is that Romie can't back the U-Haul in at a steep enough angle because the uphill gate post is in the way. Therefore, that uphill gate post needs to come out along with that first eight foot section of fencing.

The fencing is not much of a problem. A few screws, a little persuasion with a small sledge hammer, and it's out of the way. The gate post is a different story. It's pretty beefy. A six by six. We start digging at the base of it hoping that it's not set in concrete underground--but of course it is. We wiggled it, wobbled it, we even used a floor jack and tried to jack it out of the ground. No dice.

Rooting around in the empty shed (because all the tools were packed) I find a not-very-sharp tree-pruning saw. Really it's a glorified jackknife. Romie and I spend the next 20 minutes taking turns sawing at the post as close to the ground as we can. Finally, finally, finally we manage to lop it off.

Romie gets back in the U-Haul, gets it lined up over a new, pristine section of Chris and Sarah's lawn and starts backing it in toward the trailer hitch. It takes some doing with the slippery ground, but he finally gets the ball lined up under the hitch again. I am so relieved I don't even know how to explain it. We hook everything up, the trailer lights up. He starts to haul it out. The line is perfect, and the trailer is pulling straight toward the center of the (now huge) opening in the fence.


As you can see from this video, and as you can hear in Jenna's excellent commentary, we thought we finally had it. Then, for seemingly no reason, the U-Haul wheels start to spin again. Romie tries reverse. They spin. Forward. They spin. I throw a bunch of gravel under both sets of wheels. They spin. Romie climbs out and we walk around trying to figure out what is going on. Finally we realize that Chris and Sarah's soil is so compressed and the back of the truck is so low that the trailer hitch is actually riding on the ground. The triangular section of the trailer hitch is riding so hard on the ground that it's actually plowing up mud in front of it. That means that the foot of the trailer--the part that you use to raise and lower it to hook it up to the truck--that part is about eight inches under ground.

Now, I like to consider myself a pretty resilient person. But for me, this was a low point. I was thinking: This is going to be the rest of my life: I'm going to live in a Tiny House that is leaning hard to starboard. I'll be renting 160 square feet of my old back yard and sponging internet off the new home owners. Because this Tiny House is going nowhere. We are done.

Romie is one of those wonderful people who just is not easily flustered. He grabbed a shovel and started digging in the mud berm in front of the trailer hitch. I joined him shoveling in the dark, but soon we both realized this was not going to work.

Walking around the front of the U-Haul we were so frustrated. The line was perfect! But the truck had so compacted the earth on the little hill in Chris and Sarah's yard that the back of the truck simply could not lift the hitch over the little hill.

Looking at the situation I wondered aloud, "Could a tow truck pull us out of this mess?" Romie said, You know, I think it could! I hit redial on my phone.

Exact same tow truck driver: Hello?

Jim: [recognizing his voice] Hey, this is the guy with the Tiny House. We are stuck again.

Exact same tow truck driver: I'll be right there.

The momentum had shifted. The tow truck driver was on our side.

When he pulled in for the second time it was about 1 am. He jumped out and assessed the situation. He saw the good line we'd established.

Jim: I think if you back in to Chris and Sarah's driveway and run your winch cable all the way to the front of the U-Haul, that you could just pull the whole rig right out of there.

Exact Same Tow Truck Driver: I think that'll work!

So, he jumps in the tow truck (still lit up like a Christmas tree and growling like a diesel tiger) and pulls up to the mouth of Chris and Sarah's driveway. And, of course, he backs in. BEEP! BEEP! BEEP!

At this point, Chris comes tumbling out the front door in his bathrobe because he thinks his car is being repossessed. He looks over at the U-Haul and the Tiny House. Then he sees the World War I trench in his yard. It's a lot to take in.

Jim: Chris. I'm so sorry. We will take care of all of this to your satisfaction before we move. We just need the tow truck to winch the U-Haul and Tiny House out right now because we have to get it to Vermont tomorrow!

Chris: Let me move my car. (Have I mentioned Chris and Sarah are great?)

With Chris's car out of the way, the Exact Same Tow Truck Driver unwinds his winch cable, and, foregoing any fancy rigging, he simply hooks it to the front of the U-Haul. It's about 75 yards from the front of the U-Haul to the winch. At this point, everyone is invested. I am, because I'm beginning to believe I may actually live in Vermont some day. Romie is, because he just wants to get home at this point. Chris is (obviously) because he wants us out of his yard (and life). But even the Exact Same Tow Truck Driver is all in! He wants this to work.

The Exact Same Tow Tuck Driver instructs Romie to get in the U-Haul cab, but to keep the truck in neutral. The winch is going to do all the work.

He fires up the winch. It takes up the slack in the cable. It's the moment of truth. The tow truck takes on the strain and you can see it sort of squat down and get ready. Then with an almost inappropriate level of ease, the winch just pulls both the truck and the tiny house right out of my back yard.

The Exact Same Truck Driver, in an unexpected act of kindness and camaraderie, charges me about half of his swinging fee for this second visit. Romie and I jump in the U-Haul and take the tiny house on a victory lap around the neighborhood. Romie parks the enormous rig in front of our big house. Jenna had the presence of mind to get it on film. What a moment!

Romie and I head into the big house for a well-deserved, luxurious 3.5 hours of sleep before our 4:45am wake up call for the drive to Vermont. More on that adventure in the next segment: Jim- I Almost Threw Up

But let me end with this photo that Jenna took of Chris and Sarah's yard the next morning. Wow.

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Cheryl Kay
Cheryl Kay
Nov 07, 2023

Jim, I thoroughly enjoyed reading this! I would love to receive any future posts!!

Jim Martin
Jim Martin
Nov 07, 2023
Replying to

Hi Cheryl! The post after this one is already up! You can read it here:


Jim Martin
Jim Martin
Oct 20, 2023

Hey Friends, if you'd like to sign up to receive future posts, just leave a quick comment and follow the prompts. Thanks, Jim 😁

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