Greetings motorized tweed lovers, Goodyear welt-wishers, suspender fetishists, bowtie buffs and Members of the Loyal Order of the Pocket Square.

This one is for you.

For many riders, motorcycle adventuring has come to mean, almost definitionally, scrambling across hardscrabble terrain in far-off lands, riders clad neck-to-toe in armored, dust-crusted GoreTex spacesuits, their peaked helmet-visors pointing towards the dangerous and unknown, their ADVbikes modern mechanical hybrids of the destrier and sumpter…tall, athletic, and well-muscled war horses, but also capable of hauling all your crap.

I am not immune to this genre, or scornful of it. That’s how I ride (and dress and pack) when I ride in Utah or Colorado or Baja or the backroads of the Gaspé, chasing my inner Long Way Round.

But here, I’d like to open the window to a decidedly different kind of adventure ride; an urban expedition filled with multiple water crossings (via the Brooklyn and Manhattan Bridges), some expert hero sections (the near-lethal cobblestones on Jane Street), exotic terrain (Chinatown), and with 1,000 of your closest riding buddies.

Welcome, friends, to the DGR.

For the uninitiated (and there are still far too many): the DGR is not to be confused with the BDR, or Backcountry Discovery Routes of which many of us are friends, fans and explorers. The DGR indicates the Distinguished Gentleman’s Ride, “a global motorcycle event raising funds and awareness for prostate cancer research and men’s mental health programs on behalf of the Movember Foundation” (thank you, Wikipedia).

In other words, a great and very worthy reason to ride.

What’s more, a huge part of the DGR is not just the bikes, but the “fits.” Folks go all out to look their Sunday dapperest, which seems to favor (although not exclusively) mid-century British moto-haberdashery, from Harris Tweeds and houndstooth to retro open-face lids, Lawrence-of-Arabia-style goggles, Viberg boots, and expressive facial hair (even some of the participating ladies will sport ersatz stick-on handlebar ‘staches).

You can see why the ride’s mascot looks like this:

The DGR takes place in May of each year, on the same exact day, in over 100 countries worldwide. There are DGRs in Australia and Angola, Bhutan and Belarus, Cambodia and Curaçao, and everywhere in between. What unites them—and all of the 100,000+ riders who participate—is a love of classic motorcycles, camaraderie, and style. This is multiplied by the fact that it’s all for a good cause, raising awareness and money for men’s health.

Back in 2018, I first dipped my toe into the DGR by participating in the New Haven, CT ride.

This was a modest first outing, maybe 40 or so riders gathered in a parking lot a few miles outside of the Elm City…

before saddling up and rolling into town in style.

I obviously didn’t get the tweed memo, but thought corduroy would work.

I was bitten and smitten. So in 2022, I pulled on my big boy trousers, and decided to tackle the DGR NYC — far and away the biggest, best and most successful of the DGR rides worldwide.

One of the reasons it was daunting was that I’d actually never ridden my bike from the leafy, suburban hinterlands of Connecticut to the concrete canyons of NYC. And for any reader not familiar with New York metro area roadways, there’s the traffic (monumental), the drivers (aggressive), the bridges (metal, chaotic and sketchy), the tunnels (clogged and fume-choked) and the physical roadways themselves, which rate from bad to war-torn.

But my good friend Hal—a die-hard Triumph enthusiast and urban adventurer in his own right—had already braved the NYC DGR several times with his fashionista daughter (she’s actually in the fashion industry at a well-known publication), and persuaded me to go for the ride.

We rode to the city the day before the DGR (not as terrifying as I’d thought) and stayed overnight in Manhattan so we’d be fresh for Sunday’s ride. One of the most fun and exhilarating aspects of the DGR is the pre-ride gathering, which is a lot like a combination bike-meet, fashion show, and Sunday walk in the parking lot.

It’s particularly so at the NYC DGR, where riders arrive in the morning at Grand Central Terminal via Park Avenue (on the north side of the station), pass through a welcoming committee of New York’s Finest (the NYPD Highway Patrol), ride up and around GCT via the Park Avenue Viaduct (an elevated roadway that allows Park Avenue to “wrap” around the iconic Beaux-Arts building) and park on both sides of the majestic avenue, rear tires to curb, headlights pointing in, riders in their outfits on peacock patrol.

It was turning out to be a perfect (but unseasonably warm) May day for the ride…already before 9 am it was in the low 90°s. I couldn’t decide whether to wear my blazer to hide the sweat, or keep it off to try to evaporate. My friend Hal managed to remain looking crisp as I wilted.

I was riding with my own little fashionista on pillion, my youngest daughter. How she was able to ride in a caramel leather bodysuit in that kind of heat and humidity, I’ll never know. But such are the sacrifices one makes on the altar of fashion, I am told.

Gentlemen (and gentle ladies), let’s ride.

One of the true joys of the NYC DGR is that it’s an officially-sanctioned NYC event. It is chaperoned by the NYPD, which—get this—closes traffic along the ride route so you can rumble along and enjoy Gotham without worrying about cars, trucks, pedestrians, or even traffic lights. The cops ride ahead, behind and alongside the procession of 1,000 bikes, halting traffic, and blocking exits and entrances to the ride route until all the bikes have passed through.

For this reason alone, it is sheer moto-magic. It’s hard to describe the joy of having New York City as your personal bike playground for an entire morning, and getting to cruise the length of the Island of Manhattan—from The Battery up to Morningside Heights, Midtown, Downtown, Chinatown, the West Side Highway, Harlem, The FDR Drive, and even a lap of Brooklyn—with a thousand other motorcycle kooks, all (for the most part) dressed to the nines.

Every now and then, the ride pauses to consolidate, and allow for some Instagram content generation. Here’s my pal Hal & pillion in Chinatown…

And me and my pillion daughter waiting to get rolling again.

Here we are crossing the iconic Brooklyn Bridge…

The Manhattan Bridge…

Cruising down the FDR Drive, a notorious traffic shithole. Riding it freely with NO CARS and just other motorbikes was as liberating as it was surreal…

And finally, rolling into the West Village, with its charming but pucker-inducing cobblestone streets. This section with its crazy undulating pavement and slippery stones was like a BDR “hero section” for urban riders (maybe BMW is on to something with their RNineT “Urban GS”).

The NYC DGR concludes, finally, in the city’s famed Meat Packing District, which becomes the Bike Packing District for an afternoon. It’s a great area on the West Side of Manhattan, right on the edge of the Hudson River, and with tons of restaurants, shops (including the tony Belstaff NYC flagship store), and cultural sites, like the internationally-famous Whitney Museum of American Art.

I parked my Guzzi here across from the Whitney, and met the rest of my fam, including my middle daughter, who—after seeing and experiencing the bikes, joy, and outfits—insisted on riding pillion with me the next year.

The DGR folks do a great job creating a true moto-block party, with a live band and a number of interesting street vendors. Italy’s Proraso represents, and they show up not just selling product but offering street shaves and haircuts as well.

I mean, part of the DGR’s ethos is being your dapperest.

It is a scene, and I generally do not like “scenes.” But this is one scene that I didn’t just like being part of. I loved it.

And since this is also a fundraiser for Men’s Prostate Cancer and Mental Health, there are also a few speeches and awards. Turned out my friend Hal was the #3 fundraiser for the NYC DGR this year, and so was awarded a nice Revzilla gift card for his charitable efforts. It really was a joyous, purposeful, mind-blowingly and ass-tinglingly great event.

And as if wrapping it up there wasn’t enough, the good folks and ride sponsors from Gotham Depot Moto (an awesome Brooklyn motorcycle garage that’s as much a community as a place to park your bike) hosted the afterparty.

Daughter #2 rode there with me after the DGR wound down in Meatpacking. Just after a short trip through Soho and a hop over the Williamsburg Bridge to Greenpoint…

At Gotham Depot, our sweaty, thirsty, sun-baked selves were treated to cold beer, cool bikes, a thumping DJ, sizzling sidewalk bbq, and the company of fellow riders, all of whom were giddy to be there.

I mean, what else is there? Except maybe air conditioning? (It was H-O-T)

If you haven’t ridden a DGR yet, I hope this inspires you to join one this coming May. Here’s the link to find a ride near you and sign up: The Distinguished Gentleman’s Ride.

And if you haven’t ridden the NYC DGR but can find a way to get you and your bike to NYC, it’s a once-in-a-lifetime experience. For me it’s now going to be a once-every-year experience for me. It’s that fun. Hope to see you out there.