Greg's Jeep Grand Cherokee towing the custom Indian Motorcycle trailer
Real Talk

Trailer It or Ride It — Either Way, It's My Call

📅 June 4, 2026 ✍️ Greg Toope ⏱️ 7 min read 🏷️ Touring · Real Talk · Gear

In This Article

  1. The Motorcycle Gatekeepers
  2. It's More Than a Bike Hauler
  3. Riding for Two — On My Terms
  4. Family, Friends, and Dogs
  5. Health, Age, and Being Honest About It
  6. The Only Thing That Matters

I posted about my new trailer. I was excited — genuinely pumped. A custom Indian Motorcycle-themed enclosed trailer that we drove 1,000 km (620 miles) to Quebec to pick up. And within hours, the keyboard warriors showed up right on cue.

"Real bikers ride their bike. If you're trailering it, you're not a rider."

Let me be clear about something: I have always ridden to the destination. Every trip so far — Newfoundland, Montana, the Tail of the Dragon, Sturgis — I rode there. The trailer is brand new to us. We haven't even used it for a trip yet. But the fact that I bought one has apparently given some people a lot to say. So here it is.

The Motorcycle Gatekeepers

There's a certain type of person online — usually behind a profile with a stock photo avatar — who has decided they hold the keys to what makes a "real" motorcyclist. Ride every mile or you're a poser. Never trailer. Never take a cage. Never miss a season. It's exhausting gatekeeping that says more about insecurity than it does about riding culture.

I've been riding for a long time. Across every bike I've owned over my riding life, I've put over 150,000 km (93,000 miles) under my wheels. On my 2020 Indian RoadMaster alone, I put on over 20,000 km (12,400 miles) in just over a year. Now I ride a 2024 Indian Pursuit — it's in its first season and already has about 3,000 km on it, with a lot more to come. I ride when I can, I ride hard when I do, and I love every minute of it. We just got the trailer and haven't used it for a destination trip yet — but that's exactly the plan. Whether I ride the full distance or trailer the bike and ride from there, both are legitimate choices. And I'm not asking anyone's permission for either.

And before anyone questions whether I actually ride — let's talk about that for a second. I've ridden to Newfoundland for a two-week trip. Pennsylvania for a 9-day Indian Motorcycle rally. The Cabot Trail numerous times. The Gaspé Peninsula. All over Atlantic Canada, Quebec, and Ontario from our home in New Brunswick. I did a 23-day ride where we made it all the way to Montana, down to the Tail of the Dragon, and back home — hitting 28 states along the way. I've been to Daytona, Sturgis, Laconia, Americade, Wharf Rat, and Friday the 13th in Port Dover. More Indian rallies than I can count. And this year alone already has the Cabot Trail, a trip to Ontario, and a possible second run to Newfoundland on the books.

And here's one more for the gatekeepers: when I picked up my 2024 Indian Pursuit in Montreal last October, I didn't trailer it home. I rode it. Two full days. In 3°C (37°F) temperatures. End of October. Because that's what you do when you love riding — you ride it home no matter what the thermometer says.

Oh — and I only have 5 to 6 months a year where the weather in New Brunswick actually allows me to ride. So I'm doing all of that in half the riding season that some of you have. Let's see how many of the "real bikers" in the comments can match that list.

So let me break down exactly why I got a trailer, and why my reasons are completely valid regardless of what the armchair critics think.

The custom Indian Motorcycle trailer with checkered racing flag flying
The Indian Motorcycle Racing flag flies proud — this thing turns heads everywhere it goes.

It's More Than a Bike Hauler

First and most obviously — we didn't buy this trailer just to haul the Pursuit. We wanted a trailer that could do multiple things, and this one checks every box:

It can carry the motorcycle. It can carry camping gear, coolers, food, cooking supplies, and everything else you need for a week on the road. It can haul things that won't fit in the Jeep Grand Cherokee. And it can be used for family camping trips where there's no motorcycle involved at all.

"Just because it can carry a motorcycle doesn't mean that's all it can do. It's a utility trailer that happens to be perfect for moto touring."

This is a practical investment in our lifestyle — not a crutch for someone who doesn't want to ride.

Rear of the custom Indian Motorcycle trailer — vintage decals, wood panelling, and Indian branding
The custom Indian Motorcycle trailer — vintage decals, wood panelling, and Indian branding.
Custom Indian Motorcycle trailer at sunset with awning out and Indian flag flying
Sunset at camp — awning out, Indian flag flying, dogs settled in. That's the dream right there.

Riding for Two — On My Terms

Here's something the gatekeepers never think about: I'm not always riding solo.

Monique is my partner and she loves being part of the adventure — but she's not someone who wants to spend five or six days on the back of a motorcycle. She's comfortable with shorter rides closer to home, a weekend here and there. And that's completely fine. That's her choice and I respect it.

But what the trailer does is open a door that wasn't there before. Now I can plan a longer trip, she can come with me in the Jeep pulling the trailer, and once we reach our destination I can go ride all day while she does her own thing. We both get what we want. She's not stuck somewhere she doesn't want to be, and I'm not cutting a trip short or leaving her home alone for a week.

That's not weakness. That's a smart setup that makes more riding possible — not less.

Interior of the custom Indian Motorcycle trailer with wood panelling and fold-out seating
Wood panelling, fold-out seating, and Indian branding throughout — this is not your average bike hauler.

Family, Friends, and Two Dogs

We also have two dogs. If you've ever tried to figure out road trip logistics with dogs, you know exactly what I'm talking about. The trailer changes that equation entirely — there's room for everything, everyone is comfortable, and we're not turning down invitations because we can't figure out what to do with the pups.

Beyond that, we have family and friends who love camping. People who have zero interest in motorcycles, but who we want to spend time with. Before the trailer, joining a camping trip meant leaving the bike behind and packing everything into the Jeep. Now we can show up with the full setup, join any trip, and if there happens to be good riding nearby, the Pursuit is right there.

It connects two worlds that used to be separate.

Health, Age, and Being Honest About It

This is the one I don't see people talk about enough — and it's the most important reason on my list.

I have celiac disease. For most people that just sounds like a diet thing. The reality is much harder than that. When I'm away from home and eating at restaurants I don't know, there's always a risk of cross-contamination. And a bad reaction doesn't mean feeling off for an afternoon — it means days of being completely wrecked. In serious cases, weeks.

When that happens, I physically cannot ride. I cannot hold the bike upright. I cannot squeeze the brake or the clutch with enough strength to be safe. I am not riding home in that condition — period. If I'm 800 km (500 miles) from Dieppe and a flare hits hard, being on a motorcycle is genuinely dangerous.

"Having the trailer means I can bring my own food, cook my own meals, and eliminate most of the risk. It's not just convenient — it's how I make long trips possible at all."

The trailer lets me bring a week's worth of food I know is safe, a camp stove, the right equipment. It removes the uncertainty that makes long trips genuinely risky for someone with a condition like mine.

And beyond the health side — I'm not 25 anymore. Every rider hits a point where they start thinking differently about long days in the saddle. That's not defeat. That's wisdom. Using a trailer to extend how long I can keep riding — and how far — is the smart play.

The Only Thing That Matters

Here's what I keep coming back to: who cares how you get there?

Some trips I ride the full way. Long days in the saddle, solo or two-up, all the kilometres. Other trips it makes more sense to trailer the bike to a destination and then ride from there. Both happen. Both are valid. The riding is the riding — it doesn't become less real depending on what was hooked up to the Jeep for the first part of the journey.

If you can look at someone who is clearly passionate about motorcycles and find a way to disqualify them based on how they chose to get to a destination, that says everything about you and nothing about them.

I ride because I love it. I've got the kilometres to prove it. And I'm going to keep doing it — on my terms, with my family, with my dogs, with my health in mind, and with my trailer when it makes sense to use it.

If you don't like it: the internet's a big place. There's plenty of space for you somewhere else.

Ride your own ride. Let others ride theirs.