Off-Road Motorcycling Might Be The Most Fun You Can Have On Two Wheels

For years, I’ve dreamed of two-wheeled adventure. It’s why I bought my old G310GS, the baby adventure bike that served as my true first motorcycle. It’s also why I sold that little BMW, and upgraded to a more dirt-capable F800GS. But, for all that buying and selling, I’d never really taken a bike off-road. That needed to change.

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So I roped in another F800GS-owning friend, and we made a plan to ride the length of Massachusetts’ Trans-Mass Trail — nearly 100 miles of dirt, gravel, backroads, and mud. By the end, despite the concussion, the trail ride turned out to be some of the most fun I’ve ever had on two wheels. If you’re considering a late-summer off-road road trip, I highly recommend planning one out.

Photo: Steve DaSilva / Jalopnik

Planning The Trip

I live in Brooklyn, while my friend Graham lives in the wretched hive of scum, villainy, and Patriots fans that is Boston. This meant we needed to pick a trail that stayed somewhere between the two of us, in order to be Fair. We also wanted something easy, as neither of us had any offroad experience under our belts and we weren’t exactly looking forward to picking up 500-pound bikes all day. Conveniently, we stumbled upon the Trans-Mass Trail — an easy, beginner route up through western Massachusetts. Perfect.

Graham and I both have family in Connecticut, which meant we had places to crash near the trail’s starting line. Meeting up in the middle also gave me the chance to hand off the original BMW Vario cases that had come on my bike. Graham likes hard luggage, I prefer soft bags, and he was happy to buy the cases off my bike as soon as he could get his hands on them. We picked a weekend, agreed on a spot to hand off the cases the night before the ride, and readied ourselves for the trip.

Photo: Steve DaSilva / Jalopnik

Of course, handing off the hard cases meant I needed to bring them and my own soft bags. Supplying review gear for both myself and Graham meant that every bag — the hard cases, my duffel, and my hydration backpack — were full to the brim. If you’ve ever wondered what an uncomfortably overloaded motorcycle looks like, feast your eyes. That’s it right there.

The hard cases shoved the duffel forward, which pushed it into the hydration pack I wore on my back. I spent the whole ride out to Connecticut getting to know my front-mounted airbox in the biblical sense, as 92-degree heat cooked me inside my riding jacket. I drank a full liter of water from the hydration pack before even leaving the city, and I still arrived in Connecticut dehydrated and with a sore back. Word to the wise: Carry less shit on your bike.

That’s not to say you should underpack, however. Graham and I each carried tool sets, tire irons, and spare front tubes for our bikes, along with the requisite clothing and street gear for days away from home that weren’t spent on the trail. We figured that, as beginners, we were more likely than your average bear to screw something up and hurt the bike in the process. We never needed the tools and tubes, but still — better safe than sorry.

Photo: Steve DaSilva / Jalopnik

Setting Off

Technically, the Trans-Mass Trail starts somewhere in Torrington, Connecticut. This would’ve been a logical place for me and Graham to meet up on the day of the trail ride, but we had other ideas. I needed to pick up an air filter for my bike, and he needed sets of pins to re-key the locks on his fancy new hard cases. So, rather than Torrington, we met up at Max BMW in New Milford to grab our parts and sync our headset comms systems. And, of course, stare longingly at the newer versions of the bikes we already owned.

The Trans-Mass Trail doesn’t seem to leave pavement anywhere in Connecticut anyway, so we felt no huge loss by changing our start point. Even in Massachusetts, the exact path varies based on whose GPS tracks you download — the version Graham and I rode, besides our routing around closed trails, can be found here.

Finally turning off the pavement, onto the dirt trails that would make up the rest of the journey, was such a freeing feeling. Sure, the route was pre-planned and laid out in a Garmin on my bars, but we were diving off of normal roads to go roam the woods — there’s something refreshing about that feeling of adventure, of exploring.

Photo: Steve DaSilva / Jalopnik

Getting Around

There’s a whole blog coming about navigating for this trip, and the Garmin that kept the two of us from giving up and retiring to a quiet existence in the Massachusetts woods, eating motorcycle parts for sustenance. This has been a big summer for rain in the Northeast, and we dealt with washouts aplenty on the trip. Some “closed” trails were fully passable by bike, if not by car, but others forced us to route around. One had a bear, which led to a similar result.

Routing around blockages and obstacles offroad is so much more entertaining than just letting your GPS reroute you when you miss a turn on the road. It’s a puzzle to solve, a maze to complete on your map, all to figure out which trails get you closest to the point you’re actually trying to go. It’s very, very fun.

Photo: Steve DaSilva / Jalopnik

Getting Hurt

Not everything is fun and games, though. Regular readers already know about the concussion I managed to give myself along the route, when I smashed my head into concrete hard enough to leave me headachey and nauseous for days. That was with a SNELL-rated helmet, too — I shudder to think of what could’ve happened if I’d had my hair in the breeze. Even when you’re riding offroad, it’s always important to have good safety gear.

Dirt is softer than asphalt, sure, and the generally lower speeds of offroad riding mean you’re not likely to need a ton of abrasion resistance. But you still want to protect yourself from impacts, from hard knocks to the head all the way down to bikes landing on your ankles. Boots, leg armor, torso armor, gloves, a helmet — don’t skimp. Better to have the armor and not need it, than find yourself in the hospital without it.

This truck was beaten to hell, and seemingly abandoned in the middle of a closed trail. We just rode around it. Also, you can see why I prefer soft luggage, right?Photo: Steve DaSilva / Jalopnik

Finishing The Ride

As the sky started to dim, and the closed trails got more and more frequent, we got less and less eager to barrel past CLOSED – DO NOT ENTER signs. By this point both Graham and I had fallen from our bikes, and we weren’t looking to repeat the process — especially when we didn’t know how long the sun would hold out. The last few miles of the trip were an exercise in edging, always approaching our destination without ever seeming to be able to reach it.

Eventually, we did. We found the stop point listed on the GPS tracks, but arrived there by roads — and from the north, rather than the south. Still, nearly 100 miles later, we’d made it: Some random street intersection, near what appeared to be a child’s birthday party. The ending was never the point, though. It was about the trip itself.

Photo: Steve DaSilva / Jalopnik

Before the summer runs out, take a trip yourself. Grab a GPS track from a forum, rope a friend into your schemes, and set out for a new experience on two wheels. You’ll learn new ways to control your bike, discover how it acts in new situations, and you might just find that you love kicking your rear wheel out in dirt and gravel.

Worst case scenario, you try something out and don’t love it. But in the best case, you may just have a new lifelong hobby.