Before we get to these two idiots, a brief meditation. It will help make this ride report make sense.

Like many other suburban New York eighties kids, I grew up listening to Vin Scelsa on WNEW-FM in New York. And after hearing just a few of his shows (usually at the kitchen table over unfinished homework in the last few procrastinatable hours of the weekend), I became a besotted fan of his Sunday-evening sonic walkabout, Idiot’s Delight.

Idiot’s Delight was like the Schott’s Miscellany of radio shows, as eclectic and free-ranging as a Catskill’s organic poultry farm. I loved how Vin zigged and zagged, riffed and ranted, shifting from Lou Reed to the Ramones and then to something totally off-kilter like Patsy Cline, but always managing to string it together along a musical or cultural or observational theme. It was like taking a road trip inside someone else’s head.

What’s more, Mr. Scelsa’s jovial, every-guy delivery—all the more earthbound and un-DJ-like for having the imperfection of a minor lisp—made it feel like you were following along one of your best friend’s cerebral road trips. And enjoying the eclectic tunes along the way.

Back in those old WNEW days, I happened to be listening the night John Lennon was killed, and remembered Vin Scelsa taking to the airwaves to share the news. He was audibly shaken—literally, speechless—and simply dropped the needle on Bruce Springsteen’s Jungleland, letting the song speak for itself.

That night turned into a sort of impromptu radio shiva with listeners calling in from all over, and other DJs dropping by to talk, cry, reminisce, and ask why—all mediated by Vin’s poignant and very pointed choice of music. While I never counted myself a particularly avid Beatles fan, Lennon was an indisputable cultural icon, and listening to Vin and the show into the wee hours, I think I experienced the idea of grief for the first time in my teenage life.

Vin Scelsa was truly a DJ for the ages, which is sort of ironic and bittersweet now that we’re in an age that has about as much use for DJs as it does vinyl records, newspaper editors, or taxi dispatchers. I miss him. I genuinely miss that thoughtful musical curation and commentary, and the predictable regularity of a “friend” on the air, which you don’t really get with Spotify or Apple Music or DIY iTunes playlisting. I miss having someone interesting and worth listening to, a familiar voice guiding you through songs and ideas and experiences, a sidekick to the soundtrack of what’s going on in the world, or in your head, or in your life.

If you never saw John Michaud’s excellent appreciation, you can see it here.

All of this occurred to me the other weekend—radio, voices, music, friends—when I set out with my old friend Jonah for a three-day motorbike trip up to Vermont.

Jonah and I have known each other almost as long as I’ve listened to my old radio friend Vin Scelsa. We’ve been buds since college days back at the University of Vermont, and we’ve remained close even as we’ve built careers, launched families, and grown older on opposite coasts. Given my social laziness, I consider it a real life-achievement that we haven’t just stayed in touch, but that we’ve always made time to hang out, do some traveling, and stoke our mutual obsessions with (in no particular order) surfing, cars, music, and motorbikes.

We’ve surfed Costa Rica and the Outer Banks. Hooned around deserts on motorbikes. And with the exception of a single broken ankle last year (thanks to a patch of greasy mud in Utah) we’ve managed to return from all our adventures in two unbroken pieces.

The two unbroken pieces:

Here are the two (actually, three) broken pieces from last year, now finally fused back together.

So here’s where Vin Scelsa comes in. On our past motorbike trips, we’ve always experienced the adventure analog-style, alone within the bubbles of our respective helmets. We’ve ridden together but apart, navigating and narrating the twists and turns of the ride with whatever happened to be flashing through the grey space corked up between our foam ear plugs.

Two bikes, two riders, two internal thought streams. But no radio contact. Communication was relegated to hand gestures.

But this time, for this ride, we were joined by this.

Not Ali G. But techmology itself, in the form of these little black discs embedded neatly up inside our pumpkin-protectors. As Ali would say, “Is they good or is they whack?”

Well, they is actually so freaking good, it’s whack.

Both of us have had these Sena Bluetooth headsets for a while now (thank you Revzilla), and we’ve noodled around with just a few of their features. I’ve used mine to answer the occasional “where are you and when will you be home” calls from wifely (you get those when you ride). And Jonah’s used his Sena to play road tunes.

But neither of us had explored the intercom function…until now. And all I can say is holy interguacamole. You press a couple of buttons, do a little jog-dialing, watch a few lights blink, and presto—there’s a friend on the radio up inside your brain. No delay, no static, no hiss. Just someone in your head besides you.

So while we’d still be two idiots on separate motorbikes, we could delight in having someone else interesting and worth listening to in our helmets, an old familiar voice to guide each other through twists or turns or hazards or holy-shit vistas, sidekicks to the soundtrack of what’s going on inside our heads.

I know I’m late to the party, but it was kind of like a own 21st-century dawning of this:

So without further ado (Hark—I hear the moto-lions roar), and in humble homage to Vin Scelsa (I told you this would ultimately make sense) here is our “Idiots’ Delights,” a haphazard revue of our radio-enabled, three day on/off-road motorcycle adventure through Connecticut, Massachusetts and Vermont.

Thanks for the inspiration and years of audio friendship, Vin. It’s like you’re part of this ride.

Thus, I give you Idiot #1—yours truly.

And Idiot #2, Jonah (brotherman never asks for dressing on the side, which is one of the many reasons we get along.)

Now the steeds. For the first time, we weren’t riding rented or borrowed bikes, which we usually do since we’re riding far afield from home. We took two of my own bikes, a pair that I like to refer to affectionately as the “Candy-Stripe Twins.” For obvious reasons.

And twins they are—a 1200cc parallel-twin and a transversely-mounted 750cc V-twin. I planned on mostly riding my faithful ’13 Yamaha Super Ténéré. Jonah would pilot the ’16 Moto Guzzi V7II Stornello. Both bikes have varying degrees of off-road capability, which I care about since finding and riding New England dirt roads is a singular, obsessive habit of mine. And that’s what we’d mostly be doing this trip.

I’d done a fair bit of planning and route-plotting with this in mind. A few folks over on ADVrider were kind enough to share GPS tracks (thank you, Rhode Trip), and I loaded my Garmin with them.

We sort of planned a New England Dirt Opera in Three Movements. Based on the GPS tracks (and guidance from several other ADVRiders), the first and southernmost off-pavement route started around Naugatuck, CT and ran up to the top of the state in Winsted/Winchester (also known as the Town That Can’t Decide What to Call Itself).

The second movement would be the venerable Trans Mass Trail, which squiggles its unpaved way up through Massachusetts and terminates around Greenfield.

And the final, northernmost movement would be the Vermont Puppy Dog Route (aka PDR)  which runs from the Green River in southern VT all the way up to the Canadian border. The majority of these three routes run on filthy, dirty, dirt. And gravel. And a few pavement connectors. But mostly dirt.

So Jonah flew in from San Francisco on a late Thursday night before our ride, giving us some time to chill, have a beer, and play fighter pilot. Picture two idiots on kitchen counter stools at midnight, wearing motorcycle helmets and yammering on the radio “Tenner to Storny, Tenner to Storny, you copy? (fake static sound) Yeah copy—what time ya wanna say wheels up? Over. (fake static sound) Let’s say oh-seven-thirty. Rendezvous at Nespresso machine. Out.”

Motorcycling. It makes children of men. Which is the inherent joy of it.

So in the morning, after some caffeine and quick pannier-packing, and we were ready to roll.  Here’s the pre-ride warm-up sequence; the Super-T doesn’t need it, but the Guzzi really does—like me, it requires a few minutes of warm dark liquid sloshing through its innards before it’s even sentient, much less moveable.

The Flying Stupidity Brothers, in their kit and ready to split.

Besides the GPS tracks, we didn’t really have a definitive ride plan, just two end-of-day destinations. Manchester VT on the way up and Brattleboro VT on the way back down, where we had hotel reservations (candy stripe twins, meet the candy ass twins—Idiot #1 in particular might like riding on dirt, but likes sleeping on a Westin Heavenly Bed).

Along the way, we could ride as much or as long as we wanted. But having played with the GPS routes, it was clear that an all-dirt run up to Manchester through 3 states would vacuum-up 16 hours of time. So for the first morning we opted for a faster run up route 8 to Winsted, to get some early mileage under our belts before hitting the Trans Mass Trail.

Two uneventful road hours of riding and we were near the top of CT, where we stopped for provisions at the hotdog-skinny Winsted Diner. And I mean skinny like without the bun.

Watering the horses. Here’s Mr. Storny…

And Mr. Big Stuff.

I’ve been to the Winsted Diner a couple of times. The place is frequented by biker-type bikers, with their biker-type bikes. I say this without judgement, but I/we (speaking for you too, Jonah) have about as much in common with the chrome-plated/ape-hanger/leather-fringe Harley set as I/we have with Fez-wearing Lion Clubbers, Amish Mennonites or Magic-the-Gatherers. We’re totally civil, and we both obviously enjoy the ride, but we’re from other planets in the solar system.

Still, we all gotta eat.

And we all have to check in on Big, Important Things. Like whether our kids are getting to school back in California.

After a quick pitstop, on to the ride.

We headed out on 8 and up through the last vestiges of Connecticut. Going…

Going…

Going…

Gone. And across the Mass border around Sandisfield, this:

Dude let’s get on it OK Brotherman just remember last year—tank slapper death wobble dude wet clay after a thunderstorm  just ride chill until I get my sea legs again don’t be a fucking pussy don’t break my fucking Guzzi BRAAAAAAPPPPPPPP!!!!

And we’re off. By the way, and all caution notwithstanding, if you want to know what peak-happiness looks like, it looks like this.

We Trans-Mass-Trailed our way up through the left side of the state (since it’s Massachusetts, isn’t it all that way?)

Brotherman leftern Mass until Savoy then bang a right towards Greenfield dude what’s with all the Trump signs in Connecticut righty state home of Winchester and Ruger that’s bonkers all Hillary and Bernie signs here lefty state, just like the ‘Mats song…

So we wended our way up “leftern” MA through Otis, Becket, Peru, and Savoy.

The grey, overcast morning gave way to a cobalt-and-cottonballs afternoon.

Somewhere around No-Idea-Where, MA, I stopped and used my iPhone to snap this. The Garmin confirmed our blissful mid-Mass nowhereness.

Here, an admission. While we were being “guided” by the voices along the routes (tracks?) that I’d uploaded onto the Garmin GPS, in addition to Jonah I had Lady GarGar periodically chirping in my head fol-low-the-route-for-thir-teen-miles. But I was becoming increasingly certain that I had no idea what I was doing by trying to actually navigate. Or that Lady GarGar had any idea where she was sending us.

This may be because I’m an idiot. But it might also be because the Garmin engineers had no f-UX-ing idea what they were doing when they built the functionality into their system, either. It seems like you should be able to load in a route and simply follow the directions. But the way the routes seemed to load, they were in discreet “sections,” which got you between two waypoints, and then you’d have to return to the menu, figure out which waypoint you’d actually reached on the route, and then select the next one to travel to. Despite Jonah’s and my best efforts, it was a navigational disaster.

What’s more, half the time Lady GarGar would put us on pavement for a stretch, and then chirp turn in one half mile…1000 feet…500 feet…100 feet…now-turn-right dude she’s saying to turn right where the fuck are we supposed to turn there’s no road or trail it’s the middle of a cornfield fuck I don’t know let’s bang a u-ey and see if we missed something okay right behind you yep that’s a field recalculating what the fuck is she doing i don’t know you wanna navigate that thing’s supposed to navigate it’s a gps for chrissake it’s a g-piece-of-shit well let’s go back to that last intersection and get gas and figure it out..

Which is how we found ourselves here in Windsor, MA, several hours after stopping in Windsor, CT. (If we make it to Windsor VT, do we get a prize?)

Watering the horses.

With tanks full and Lady GarGar (a third but thoroughly unreliable voice) in our heads, we headed back to dirt roads and dirtier language, cussing about her inscrutable so-called guidance. But it actually didn’t matter a lick, since we had nowhere to be but riding, and the riding was so gosh-darn delightful.

Dirt yielded to pavement after we made that right and noodled our way over towards Greenfield.

Greenfield was not what I’d call a high point of the ride. It’s a typically (and depressingly) beat New England town, with what must have been a once-charming and attractive main street a shell of its former self. Even on a sunny day, the place feels like surrender.  Peeling, nineteenth-century mid-rise buildings house empty storefronts, or off-kilter enterprises like a vape shop, second-hand music store, or budget furniture showroom. People-wise, the sidewalks seem a little like a rehearsal take for The Walking Dead. As this Trip Advisor reviewer notes:

“[Greenfield] seems to have been overrun with societies [sic] “less desirable.” Shopping downtown was downright scary, hassled by the homeless and apparently mentally ill. I couldn’t walk ten feet without being surrounded by a cloud of second hand smoke or dodging skateboarders, kids on bikes or a man walking with a traffic cone on his head.”

Sigh. Like too much of New England, Greenfield has succumbed to the post-oxycontin heroin epidemic, which must have made it compelling (upsetting?) enough for Anthony Bourdain to include in a 2014 episode of Parts Unknown; hometown native Matthew Becklo explored it further in this heartbreaking post. We two idiots took several laps up and down Main Street looking to score some, well, lunch, but were having a hard time committing to anything because it all looked so sketchy.

So we settled on the simplest option—a straight-up pizza parlor. We parked the bikes outside, but the general street vibe (and I’m a New Yorker) made me forgo my custom of just leaving my bike crap piled up on the handlebars. GPS, gloves, neckbrace, jacket, and helmet—all came inside.

As it turned out, the only other people we’d be sharing Greenfield’s finest pizza joint with (besides the decent and hard-working owner) was a skinny, tattooed kid in a wife-beater, and his clingy, hollow-eyed girlfriend. Cue the Lemonheads:

A coupe of slices, a surprisingly decent salad, and we were out of there. I don’t mean to be uncharitable or judgmental. But Greenfield might better have been dubbed Pittsfield. But then, Massachusetts already has one of those too, imprisoned by the same New England scourge.

Grim and sad. But we were out for dirt and joy. So onwards to Vermont.

We crossed under I-91, looking for a side street that would take us to Green River Road, a picturesque dirt and gravel ribbon which runs along the Green River and threads its way up into southern Vermont. I rode it several years back on an F800GS, and was looking forward to crossing this…

But the Green River Covered Bridge was under construction, and we wound up following a long but pretty detour over the hills and through the woods.

At some point, we crossed into Vermont, which always feels like home to me. Thanks for hanging out the welcome sign!

If Emily and I ever build a place up your way, we might have to settle down on my own personally-branded dirt road. Relax, Jonah—we’ll look for a road for you, too.

We stayed on the PDR it until it intersected VT Route 9, the Molly Stark Byway, and hopped on some pavement  to head west, since our end-of-day destination was in Manchester. There’s a scenic lookout and store in Marlboro, where the Brotherman and I stopped for some Birch Beer and VT swag for Jonah’s kids. My guys have aged out of refrigerator magnets and maple sugar candy a few years ago, but are still not quite of age for a craft beer sampler. Plus no pannier room…sorry kids!

The remainder of Friday’s ride was mellow, aimless fun. We headed north and bumped into the West River, which after about 10 hours of riding looked like a good place to cool off with a dip. And it was.

Then Route 30 through Newfane and Townshend, and up and over to Manchester, where we arrived at dusk at the Kimpton Taconic for some hard core moto-camping.

They were hosting some kind of black tie benefit (in Vermont?), and the place was jammed, so we got to conclude the day’s adventure fittingly: off-road.

Then showers. Civvies. Bourbon. Beer. Chow…

And then this: ever wonder what two middle-aged idiots sound like after 12 hours on motorbikes and a couple of drinks, falling asleep in a hotel room filled with stinky moto-crap, with the TV left on all night?

Just like that, friends. Just like that.

Tomorrow, the Idiots delight in a lap of Vermont, and some Mass Trail joy in reverse…