A Ride by the Book: The Trans Mass Trail

Despite the interstates and commuter lines, Walmarts and Home Depots, crumbling industrial-era mill towns where longarms, brass fittings, mantle clocks and hats used to be made, despite Fairfield County’s tri-state gravitational pull, the Boston Post Road, Boston itself, urbanized and under-serviced cities like Bridgeport, and greater Hartford’s well-insured suburban sprawl, New England still has plenty of this.

Roads that seem to go nowhere…

Forests that feel like they’ve sprung from the pages of Tolkien…


And mountains and hills so lush and green, they can make your eyes hurt. Enchanted ground, indeed.

That’s why I head north from our home in the southernmost corner of Connecticut each summer, to take a long-cool drink of New England, ideally from the saddle of my motorbike.

Last summer, I slaked my thirst with a two-day, off-roadish adventure through Massachusetts, Vermont, and New Hampshire on the venerable Puppy Dog Route (aka PDR), which thumbs a wet nose at the comfort and speed of I-91/89 for the less-linear, more chaotic joy of gravel and dirt. I say “-ish” because I only completed part of it.

Here’s the PDR’s very beginning.

Most of the PDR qualifies as road, although there are varying degrees of “roadiness.” As it waxes and wanes through the woods of Vermont, the PDR is sometimes fast, smooth, hard-pack, and rurally residential. Other times, and through more challenging stretches, it’s rutted, single-lane two-track, or even what-the-hell-am-I-doing-here goat trail. 

I mainly give that ride an “-ish”  because it lacked in completeness, and I’m a completist. I picked up the Puppy in Greenfield, MA, riding along the Green River until the Bay State became the Green Mountain State, right around here.

But I only made it as far as Manchester before packing it in for the day, having just cracked the lower third of the route on my trusty (but ass-aching) BMW F800GS. Someday I’ll ride the complete PDR, but last summer, I just bit off and chewed part of it.

So this summer, and with a more comfortable new steed, I wanted a bike-bonding experience on a route I could actually complete during a 48-hour moto-liberation from commuting, work, wife, & kids.

Oh, did I mention I got a new bike? (Link will take you to that story.)

So I scoured ADVRider looking for another New England adventure, and found a route called the Trans-Mass Trail. (Shout-out to Keith Hedlund, the ADVRider who GPS-plotted the whole thing in the first place, and was kind enough to share some tips with this fellow rider.)

The TMT is a less-northerly variant of the PDR that bisects the Commonwealth of Massachusetts from bottom to top, almost entirely on dirt. Even better, it can be covered in a single day, which would give me extra time to ascend even higher into Vermont before nightfall, so I’d have more dirt and distance to play with the next day before hightailing it back to exurbia. 

Sound like a trip? Let’s book it.

And speaking of books, you’ll notice this ride report is filled with old and well-worn covers and spines (and not just mine)…

I’ll explain. 

My darling wife—no fan of the bike habit (she’s a hater, but purely out of love)—actually participated in this year’s trip planning, Googling-around to find a place for me to stay. I’d planned on just riding until dark and then winging it wherever I landed; she was kind enough to reserve a room at the undeniably lovely (but unfortunately-named) Windham Hill Inn in West Townshend, VT.

(Am I the only one who remembers and recoils from Windham Hill Records, that new-agey label from the eighties?)

Thankfully, the first floor of the Inn isn’t lined with peeling Yanni LPs, but instead with shelf-full after shelf-full of anitquarian books, whose fading titles were eerily prescient milemarkers for my two-wheeled journey.

So let’s get booking. You’ll see what I mean. 

Saturday dawned with that jittery, anticipatory, pre-ride delight I get every time I’m about to ship off. All pannier-packing, pressure-checking, tailbag-strapping, and GPS-fiddling.

As part of it, I begged a sleepy refresher course on the GoPro I was borrowing from my daughter Ivy. (I love that camera for its bomb-proof, wide-angle pleasures, but the user interface is shocklingly Casio for such a post-digital device.)

Thanks to her, I got it sorted enough to actually shoot a picture of my baby beluga, fully-laden and ready to roll.

Still, I had one important waypoint to hit on my way out of Connecticut before ascending to the Mass of Dirt.

My youngest, miss Maisie (a.k.a. Mayo, Maybe, and Mochachino) was playing in a soccer game up in Farmington, just outside of Hartford. Another parent kindly offered to ferry her there on four wheels, so I didn’t have to strap her to the tailbag and worry about cleats scuffing my panniers.


So with Mayo on her way, I set off on mine: an hour-and-a-half of slab-riding up I-95, Route 8, and I-84.

Thankfully, this is no longer a literal pain in the ass, since my new Super-Ten feels like the QE2 compared to previous, smaller-displacement vessels. The engine room hosts a 1200cc parallel-twin that chugs along with cruise ship authority. And to go with the nautical metaphor, the entire craft is propelled by a screw, literally. She’s a shafty, driven not by a chain but a long, whirling rod that spins power from the engine to the rear wheel’s final drive. Kinda like this.

Look Ma! No chain! Shafty and crafty.

What’s more, she’s truly zaftigwhich on the highway, is a good thing. Her captain’s chair is relatively plush, especially with sheepskin. Protection from the elements is good with her stock windscreen, but even better with the adjustable X-Screen extender I added (best farkle so far). Adjusted just so, it creates a pocket of calm, un-turbulent air that makes highway sailing not just bearable, but enjoyable. 

So Captain Comfortable here enjoyed his pleasure cruise from Fairfield County up to Farmington. And he may be the only parent that’s ever shown up for a U13 soccer match wearing full ATGATT, on a trip-ready ADVbike.

Eat your heart out, minvans.

Here’s Cathy, our friend who kindly gave my Mayo a lift to the game.

And so I got to enjoy a few hours in my astronaut outfit, splayed out on Astroturf, watching Mayo and the other kids on her team “look for space.”

(Parents who seem to know more about soccer than I do yell this, a lot.)

But as I sat there and cheered our team on, I couldn’t help feeling something a little incongruous about the intersecting orbits of my normal, public, parenting life with my slightly-obsessive, private, solo-riding life. The twain rarely—if ever—meet.

Normal home life transpires outside my helmet, on soccer fields, in flip flops, with kids, moms, dads, schools, and supermarkets, hours and days and weekends and years deeply—happily—engaged with nurturing, nudging, feeding and schlepping—all of the warm domestic rhythms of suburban family life. That’s how these go by.

But my riding life transpires alone, inside my helmet, hyper-sensitized to time, space, and mortality. It’s deeply private and self-reflective, during which time my brain seems to run several parallel, incongruous narratives about what I value and love, the inherent motor-complexity of the moment (few things require such total mind-body-hands-feet commitment as riding a motorcycle), and the delicate, terrifying balance of joy and risk.

The closest thing I can compare it to is surfing, which I also usually do alone among strangers. On bigger days, I’m simultaneously awed by the power and beauty of the ocean, gleeful at the moments when I manage to make it to my feet and glide down the face of the moving wedge, and terrified of the hold-down after it folds in on itself and crushes me.

Me, pre-crushing, a few summers back on Cape Hatteras.

Riding’s not dissimilar. Awe at the power and beauty of land-surfing across asphalt, the waves of green and sunlight washing through an open face-shield, glee at those moments of precise lean, crisp transition, and bowel-stirring traction, and terror—sharp, bowel-emptying terror—at the sudden awareness that the lady on her iPhone in her Escalade with a venti double-skim latte could turn you into a sad, 15-second segment on News 12 Connecticut.

All of which brings me back to this.

Find space, Maisie! Find space!

They did, and happily won. But speaking of space, it was time for this spaceman to find some space, too.

So thanks for the lift, Cathy. Be a good girl, Maisie. See ya, soccers!

Time to start exploring the upper atmosphere of this.

I launched up Route 4, heading northwest along the Farmington River, and through the sundry towns that were birthed when Farmington—once the largest community in the proto-American Connecticut Colony—atomized into its now smaller parts. 

One of the first places I passed through was Unionville, a pretty little mill town on the Farmington River, once home to a bunch of nuts.

More specifically, the Union Nut Company, a nineteenth century forger of nuts and bolts. I’m not sure if this mill on the river was their factory, but it was someone’s.

The view from the bridge of my cruise ship.

It was turning out to be a perfect riding day—low seventies, plenty of fat, lumpy cumulus clouds, and stretches of blue sky to go with the uncluttered asphalt (except on this bridge). So I ambled along this… 

…following the Farmington river up to Collinsville, where I had some nice views of dozens of kayakers and paddleboarders taking advantage of the lazy water and summer warmth. Then I picked up the Albany Turnpike and connected to Route 179, cruising up through New Hartford until I popped out at the top of Route 8, here:

Winsted, or Winchester (depending one whom you ask) is sort of the last-stop in the Litchfield Hills of Connecticut before you cross into Massachusetts and the lower Berkshires. The town has either a branding problem or an identity crisis, since it refers to itself interchangeably—and often with a slash—as “The Town of Winchester/City of Winsted,” even on the Town/City’s own website.

Frankly, I’m going with Winsted.

After seeing this, how could you not?

I stopped here for lunch at The Winsted (not Winchester) Diner—a hotdog-skinny, railcar joint that takes the idea of small to new heights (widths?)

With a distance of about 11 inches between the counter and grill, you can quite literally reach across to cook, plate, and serve yourself a burger without getting off your stool.

And you’ll notice from the picture that neither the doors to the refrigerator nor the microwave can even open fully in the diminutive space. In this age of fire codes, health laws, and zoning requirements, it almost looks illegal. But size was no obstacle to some pretty decent chow.

The guy behind the counter (I should really say, “the guy impossibly wedged between the fryolater, cooktop, and counter”) was super into his craft. He hand-cuts fries from raw potatoes with a wall-mounted slicer, and slow-cooks his own BBQ over days with a smoker out back. He’s the very literal human definition of chief cook and bottle washer.

And he whips up plates of joy like this, a pulled-pork slider on a grilled bun with homemade slaw and fries.

“It’s not actually glistening with diner grease, honey. That’s just the lighting…”

Well done, Winsted Diner. Well done.

And so, with a warm, pork-filled belly and glistening smile, I set off for the upper atmosphere of the Constitution State, pausing here in Colebrook to pray for safe passage as I punctured the thermosphere and entered the next level of New England.

Breaking the Mass barrier.

And within just a few minutes of entry, I arrived at The Beginning: the intersection of Sandy Brooke Turnpike and Bood Hill Road, the very first waypoint on the Trans Mass Trail, and the start of several hours of transcendental dirt meditation.

Here’s big white little red riding hood, just before venturing off into the woods.

Au revoir, tarmac.

And so, I started to ride…and ride…and ride. It’s hard to describe the singular joy of riding down (up?) a New England dirt road in late summer, with no plan, no schedule, no cars, no people, 5.1 gallons of dinosaur juice in your gas tank, and nothing but a heartbreakingingly pretty, endlessly-unfolding ribbon of dirt and crushed stone that goes on for hours.

Here’s a typical stretch, with a kiss of red making an early appearance in late August.

Evidently, part of the Trans Mass Trail also traces the Henry Knox Trail, aka the Knox Canon Trail, a Revolutionary War-era artillery byway from Fort Ticonderoga to Boston, and named after Colonel Henry Knox, who was commissioned by George Washington to transport dozens of captured brass and iron canons to a Continental Army encampment outside of Boston in 1776 (thanks, Wikipedia).

 My kind of road sign. 

It was a little strange covering so much ground without knowing exactly where you were; while I rode from GPS waypoint to GPS waypoint, there isn’t any real indication of what town you’re in, or how much progress you’re making. Just imagine if you were Colonel Knox.

Here was a rare exception. (Hi, Dina. Just passing through…)

Forget about the title—focus on the author. Didn’t I say those books were prescient?

I used my daughter’s GoPro to capture the essence of riding the TMT. Unfortunately, I didn’t have a helmet mount, so all I managed to shoot was this sketchy, one-handed take. Since you need a clutch-hand and a throttle-hand on a bike, doing a third thing like shooting video—unlike in a car—is physically impossible. Well, almost.

The squeeking, popping audio from manhandling the GoPro was so awful that I abandoned it for—what else?—a Guided by Voices soundtrack.


Hey, it may not be perfect filmmaking, but everything else about it was.

Dirt, gravel, fields, old stone walls, oak, maple, poplar, birch, an occasional colonial farmhouse, warm New England summer air, and the chugging of my Super Ténéré beneath me. 

Trans Mass, how do I love thee?

By the time I’d gotten about a third of the way up the state, the grand total of vehicles I’d seen on the trail came to a whopping seven. In stark contrast to everyday road riding, you have to worry more about trees pulling out in front of you than idiot drivers. For what it’s worth, I was constantly on the watch for deer, but during mid-day August, not so much of a problem. In fact, never laid eyes on one.

Every now and then, my into-the-woods spell was broken by a paved section or some other brief assertion of modernity, reminding me that I wouldn’t be running into Colonel Knox and his men, hauling canons. In this case, it was a bridge crossing the Mass Turnpike, the highway thrumming away below.

Fortunately, the Trans Mass Trail has very few of these sorts of things to interrupt your dirt dream.

I kept climbing up through the state, and at some point, deep in the woods, I came upon this: a hearth without a home. Maybe razed during a skirmish with some Redcoats?

Not long after, I encountered the first and only other rider I’d see on the entire TMT. He, like me, was out for a summer bimble, although he lived in Massachusetts and didn’t really have a destination in mind. 

And wouldn’t you know, he was also on a Ténéré—which is unusual, as it’s generally a rare bird among ADV bikes (everyone else seems to ride BMW GS’s). Nice to meet you, Jim. Two ships, passing in the waning daylight.

At some point about two-thirds the way up the state, the Trans Mass Trail arcs off to the east, and funnels you towards Greenfield. But I chose to do some improvising here, and stayed west of I-91, wending my north on Route 112 through Ashfield, Buckland and Shelburne Falls. The top of Massachusetts became less dirty and more pavement-y. But it was still delicious.

 Take it to the bridge, J.

With handy data from my iPhone (time stamp on the pictures), I was able to see that I’d entered Massachusetts around 2 pm, and finally concluded the Trans Mass Trail (at least my slightly detoured variant) around 5:30 pm, a little more than three blissful hours later.

All I can sat is wow. Wow wow wow wow. What a ride. Thank you, dirt. Thank you, stone. Thank you, Colonel Knox, the Commonwealth of Massachusetts, Otis, Keith HedlundEnse petit placidam sub libertate quietem.

Which brings us to Chapter Two of this ride by the book, and my first true love.

Hello, old friend. Nice to be back.

I know I’m being a repeater here, and have covered the same ground in other ride reports, but here’s my “Vermont Thing.”

I first came here as an 18-year-old college kid; I met my wife Emily and many of my oldest friends here in Vermont (at UVM). As a family, we’ve spent weeks of summer, winter and fall here over the years, from Waitsfield to Warren, Winooski, Manchester, Montpelier, and everywhere in between. Even though I’ve developed a power-crush on Maine lately (it’s kind of a bigger, wilder, woolier version of Vermont, more libertarian, less eco-Stalinist, cooler about motorbikes and snowmobiles and firearms (the sporting kind), and with better seafood), Vermont keeps pulling me back, and I find it hard to resist her.

So every time I cross the state line, I smile and host a mini-homecoming parade for myself, somewhere up inside my soul.

Why, look at all the people already lined up for my auspicious return! A hero’s welcome!

So nice of the townsfolk to festoon downtown with flags and other welcoming ephemera. The BluRhino propane cage was such a nice touch! Sooo nice to see all of you! Glad to be back!

I thanked all the invisible citizens, and toasted myself with Vitamin Water and a Cliff bar. Then I assumed the Throne of Honor in a dusty Adirondack chair on the front porch of the Jacksonville General Store, waving to all of the assembled masses. Of Subarus.

Well, one. 

Vermont, I love you. Thank you for loving me back, even in my imagination.

The Jackonsville store sits right at the intersection of Route 112 and Route 100 (aka “the Skier’s Highway”), so I grabbed the Super T-bar and got moving. Not long after, I felt my chest vibrating (iPhone, not implantable defibrillator yet), so I pulled off at this sweet spot in Wilmington to see who was calling.

It turned out to be an unusual but important-to-deal-with work issue cropping up on the weekend. So I made a few calls, sent a few emails, and hung out here until the issue was resolved.

Nothing like technology to let you do business from the beach.

As I headed farther north, and the sun header further south (I know, I know—but you get the metaphor), the sky cleaned up nicely, and created a beautiful cerulean backdrop for the rolling green glory of southern Vermont. I snuck a side-trip up this hill to get some fresh dirt under my Ténéré’s fingernails…

And after a brief dirt reprise, headed back to 100 North, where I was treated to a Vermont sunset for the ages. Here’s a snippet of it from my Super-T.


How awesome is that?

Not long afterwards, and in the fading light, I rolled into ski country proper and made a quick pic-stop here.

I fantasized about tackling a few blue trails on this, but I didn’t think the management would appreciate it.

Then, just as I was pulling out of Mount Snow, I witnessed a stunning, incongruous sight:

Crossing the road, and walking down to the lodge area where I’d just come from, was a passel of bearded Hasidic Jewish men, in full Sabbath kit—Shtreimels (those spectacular fur hats that kind of look like sable-covered cheese wheels), Peyes, Bekishes (three-quarter length black coats), black pants that stop at the knee, and white-stockinged legs with black shoes.

Exactly like this, but crossing Route 100 in Vermont. (photo: Google Images)


It was totally out of context. The effect was sort of like seeing a ski racer walking through Williamsburg in August, in a POC helmet and G-suit, like this.

(That’s my son Noah in the middle, at a race last winter, but not in Brooklyn.)

The Hasidim must have been participating in some sort of weekend religious retreat at Mount Snow, which I guess was looking to fill rooms with a different set of faithful than skiers.

I’m Jewish myself, largely irreligious but culturally-identifying. But here I was, wearing my own kind of bizarre (but purposeful) get-up, out on a Sabbath evening, praying at my own ersatz altar (it just happens to have handlebars and takes me to beautiful places in God’s world where I can marvel and express gratitude), and yet regarding some distant members of the Tribe as if they—not I, the guy in the space suit—were the brothers from another planet.

So I did the only thing that seemed civil.

I flipped up my visor, blipped the throttle, and burbled past them, offering a cheery “Shabbat Shalom!”

It was their turn to be surprised, this time at the unlikelihood of Hebrew coming from the helmet of motorbike-riding astronaut.

They returned my greeting, and  I went on my lapsed, heathen way.

Screen Shot 2014-11-12 at 6.21.29 PM

By now, dusk was settling in, and I still had a fair bit of ground to cover before arriving in West Townsend, the apogee of my day’s adventure. But as I rode on, I started seeing signs indicating that Route 100 was closed ahead.

According to my GPS, it was the only road connecting where I was to where I was going. So I hoped that whatever was causing the closure was negotiable, and that I’d be able to ride around it. 

As I reached Wardsboro, the road indeed came to a screeching halt, with blinking roadwork barriers and signage indicating that Route 100 was (to borrow a phrase from from the Wizard of Oz) positively, absolutely, undeniably and reliably CLOSED. (photo: Google Images)


Unfortunately, there wasn’t a detour sign in sight.

My first reaction—since it was starting to get dark—was to gather up some testosterone and just motor through it. So I gingerly rolled down the deserted, gravel-strewn roadway. But about a quarter mile into my scofflaw-dom, some alarmingly tall headlights appeared ahead, and soon it was clear why. One of those Titan-class dump trucks—the kind you see on Modern Marvels working oil sand mines in Alberta—was bearing down on me.

Ever get the feeling you’re someplace you really shouldn’t be? 

So I abruptly u-turned, and sped back to the road closure to figure out plan B.

I spent some time fiddling with the GPS, trying to see if there were any back roads that might connect me with Route 30 a few miles north. One faint line looked promising, so I headed for it. It took me down a narrow dirt road through the woods, with only an occasional (and dark) house every quarter mile or so. It was definitely spooky, and I was definitely spooked. I had maybe a half hour of half-wattage daylight left, and didn’t feel like trail-riding—lost—through the Green Mountain National Forest at night. 

Then, at a clearing in the woods, and separated from me by just a stone wall and maybe forty yards, I saw this:

Dude, that’s a bear.

A black bear.

You’re alone. In the woods. In Vermont.

And while you fiddle with your iPhone and try to decide if it’s a really big cub or a modest-sized Mama bear, someone might be deciding that Connecticut Jewish Adventure Rider is what’s for dinner. You’d get mauled, hauled into the thick dark woods, and eaten. And you know what?

All they’ll find is your stupid Ténéré, lying on its side, idling. Maybe you’ll make it to America’s Most Wanted as an unsolved murder mystery. Your wife and kids will never know what happened you.

Such were this:

Until I remembered, “dude, you’ve got a throttle. Use it!”

So instead of getting hauled off into the woods, I hauled ass out of there, and finally rolled into here just as darkness descended on the day.

Hello, Windham Hill. I’m so happy, I could hug Yanni right about now.

So whether through luck or providence, I’d arrived unscathed. I parked and powered down the Super T, bidding good-day to Maisie and her space-seekers, the Farmington River and nut factories everywhere, skinny diners and fat adventure bikes, miles and miles of delicious Trans Mass Trailmix, Colonel Knox, Captain Hasidim, the good people of Jacksonville, Snow Mountain, Mama Bear, and coming home to a bed that’s   j  u   s  t   right. 

Thus, we close the book on Saturday, retiring to a hot shower, a warm dinner and cool sheets, grateful to be…

3 responses to “A Ride by the Book: The Trans Mass Trail”

    • Enjoy it and ride safe. Hope you have fair skies. Was up around Otis/Becket the other weekend…tried to do a TransMassTrail starting point drive-by, but couldn’t remember where it was!

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