What do you think of when I say bike culture? Does your mind go to the backs of beer soaked bars where the smell of gun oil, cigarette smoke, and urine mix to form a gag inducing musk only the manliest of man can stomach? Or do you think of men born with wrenches in hand who ride out of the womb on ear-busting hogs clad all in black, who piss straight octane and have 20w-50 running through their veins? Sunday’s Distinguished Gentleman’s Ride in San Francisco couldn’t have been further from these archaic images of the rough and tumble biker.

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Formed only three years ago, the Distinguished Gentleman’s Ride, or DGR to those in the know, aims to bring together classic motorcycle enthusiasts with a penchant for dapper threads all while raising money for prostate cancer. Sure, everyone pulls out the checkbook for Susun G. Koman and the cute pink ribbons. But co-workers will give you a slightly less energetic look when you say you are collecting money for a motorcycle ride in support of this less publicized type of cancer that centers around a man’s private parts.

On Sunday, an eclectic mix of motorcycles and an even more varied mix of riders rumbled into the parking lot at Pier 30 in San Francisco with the usual biker nonchalance. Before long there were over 150 riders on everything from Royal Enfields to Ural’s with sidecars and homemade junkers running coolant through Jack Daniels Old No. 7 bottles. There were true vintage, refurbished vintage, modern classics and some had put blood, sweet, and tears into every bolt, while others had left such matters to a well-paid mechanic.

I myself was riding a 2013 Triumph Scrambler 900 and wearing a newly acquired Austin Reed suit with a Union Jack helmet and goggles. I had been worried that those hip bastards in San Francisco would bring their A-game and spent the previous day frantically scouring the Haight in search of the proper attire for a gentleman’s ride. As I sauntered around the parking lot watching more and more riders arrive, I soon realized the crazier the better. From three-piece suits to a mechanic onesie, all of us did our best to look like we were traveling back to the days of smoking on airplanes and old fashions for breakfast.

I hadn’t known what to expect, and wondered how many people would turn up and whether they would be as enthusiastic as I was. What I found was an incredible gathering of men and woman who were as passionate about bikes as any ‘true’ biker I have ever met. There was also an easygoing sense where all the riders were eager to share their passion and not afraid to poke fun at the conventional stereotype of the biker community.

Sometimes the biker spirt is defied by that leather-clad, beard sporting, Harley driving guy. However, sometimes the spirit is also found in that suit-wearing skinny kid who just spent the last two years building his dream Honda 450 from four spare bikes so he could get out and help fight prostate cancer.

The world is a weird place. Ride it!

My memories of Portugal are fading from me. I’m trying to wrap my arms around them. To pull them close. To conjure the most minute details from the trip at will. The friends I made. The cows with the giant cowbells, standing on the side of the road. Riding through the most picturesque Portuguese cities and having complete strangers yell greetings and cheer me on.

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I’m trying to remember the texture of the most exquisitely delicious squid to ever reach my lips. To hear the laughter of the Canadians in my ear and the dirty jokes from the Irishman. I want to feel the ache in my legs again as I attempt to climb to the highest peak in all of Portugal. To recall the laughter as the newly-wed shares his water bottle with a donkey. To feel the thrill and relief while hanging off the side of the “team” car. To lay back once again on my pillow in a palace or a former monastery or inside a walled city.

But even as I sit here processing a week of riding my bike in a country I never planned on visiting, it’s all fading. My time on the road with inGamba is packed with treasures but only a painful few will stick around.

This trip was not a cush roll through the scenic countryside, like in some bad romance novel or Hollywood movie. The crew at inGamba are as serious about pedalling the bike as they are about squid and vino verde.

The Portugal Randonnee is a trip with way too many kilometers covered and too many meters climbed to translate into a definitive description.

From the moment I step out of the car into the Old Quarter of Lisbon the feeling of relaxation washes over me.

I know little of the rich history but yearn to understand. The smell of the ocean reaches out to me and the quality of the light is enticing. I wander the tiny cobbled streets making photographs of anything and everything.

I am staying in a palace, a literal Palace, just below the Castle Jorge.

The purveyor of the Palacio Belmonte is a historian. I can hear her in the other room sharing her knowledge of the palace’s history which I am calling home for the night. It’s not so much what she is saying, but how she is saying it. The Portuguese history has pain, but also much pride.

Joao, the public face of inGamba, is wandering about making introductions, mine included, while conducting business on his phone. The business seems important. He is immediately likable.

Dinner on the first night is like a scene out of a foreign film. The group and I are whisked from the Palacio in black sports sedans (OK, one car and one van, but still), racing through the cobbled street only to arrive at what must be one of the most popular seafood restaurant in all of Lisbon. The line out front is daunting. But with Joao, lines are trivial. We excuse ourselves over and over as we pick our way past the poor people who have to wait, past the packed patrons and finally upstairs to our private table.

From the moment we arrive until the moment we leave, waiters scurry about our table making sure our glasses are filled with vino and our tummies are filled with seafood. The delights from the sea come at a dizzying pace as we are presented with shrimp and crab and clams. It’s not the food or the wine or the early stages of relationship building that make the evening. It’s all those things in concert.

Conversations about jobs and families and past bicycling exploits buzz around the table. The group is a good one. There are four couples, including the honeymooners Ryan and Andrea, from Vancouver. I like them right from the start. They are gamers. They are ready for anything and everything this trip is going to throw at them.

As we’re escorted back to the palace for a brief meeting about sobering things, like riding etiquette, wake up calls and laundry schedules, I become painfully aware my time in Lisbon will be way too short. I promise myself I will return.

The group is offered two options for the first day’s adventure—either the originally scheduled 130km or a more moderate 90km. Things break just about how I would predict by looking at the group, with the skinny ones taking the longer option.

The newlyweds, the triathlete and her athlete boyfriend, the “kid” from Apple, the anesthesiologists hammer, the big fella with the accent from down under and “returning from injury” Gary, all opt for the longer route.

The Jersey girl and her Oregon husband, a dirty-joke-telling Irishman, the New Yorker, the video producer dude, the adorable Canadian financial planning couple and I, all opt for the shorter route.

I think I have chosen wisely, but we will see.

Overnight rainstorms sweep through Lisbon, pummeling the roof of the Palacio and it reminds me of being a kid on vacation in Florida. The storms roll in over the ocean and the rain pounds against the earth with furry.

We wake to wet earth and ominous skies. We take breakfast on the veranda at the Palacio and the conversation has a slight air of nervousness, but everyone is ready to get this party started.
After a short transport we arrive in Alcobaca and are introduced to our bicycles for this ride. It is quite a site to see a row of matching Pinarello Dogmas all dressed in black with Italian colors striped inside the fork legs. And as an added inGamba touch, each bicycle has the rider’s name emblazoned on the top tube, not unlike what you would find on the Pro Tour.

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The early kilometers click away as we each find our place within the group. We have a beautiful black Mercedes as a lead car and a van following behind us. We regroup a couple of times and everyone seems to be in great spirits. We finally stop at around the 50 kilometer mark for a caffe and as we sit under an awning enjoying our beverage the clouds open up. It pours down rain for no more than six minutes and it will be the only rain we see all day. We feel blessed.

The only real climb of the day comes at the end and is a reminder of what we have in store for us tomorrow. The ride today is just under 90k with 1100 meters of vertical. But tomorrow will bring more than double the climbing, in the same distance.

We spend the night in a converted convent and dinner is another celebration. I can’t help but notice a theme emerging at the late night meals. The meal starts with sparking wine, then bottles of white, followed by bottles of red and finally a lovely port to round out the meal. I try to pace myself, as do the riders on either side of me. But there are others who seem to be prepared to go the distance. I sleep well for the first time on the trip and I am grateful.

I wake early to the sounds of the team bus we will use as transport for our gear and bicycles. The conversation at breakfast is all about the climbs ahead and for good reason. Our second day in the saddle brings the biggest climbs of the week.

A double paceline forms from the gun, with the added bonus of having Portuguese professional rider Tiago Machado sitting on the front. The group takes turns riding beside Tiago, chatting him up about his life in the pro peleton.

The pace up the first climb is pretty brisk and I forget to take time to enjoy the countryside because I’m staring at my stem.

Over the top of the first climb we find a wide-open, rip-roaring decent and I attempt to chase Joao off the backside of the mountain. Even though he has taken on a little post-career paunch, Joao knows how to handle a bike. Hammering down the sweeping descent and using every inch of the road from side-to-side, he actually sets a Strava record on the way down.

If the first climb was difficult, the second climb is soul-crushing, leaving riders strewn all over the mountain. Climbing up above the tree-line the terrain looks more like a moonscape than a landscape.

I try to enjoy the sweeping vistas of Portugal, the mountain lakes and the company of my fellow riders, but the climb never allows you to settle into a rhythm. The road deceptively keeps changing grade, causing the body to constantly wonder if it should get into the follow van and take a nap.

It was agreed universally at dinner that even though the ride was a serious day’s work for everyone, we were all glad to have done it. The reward of an epic day in the saddle is a couple glasses of wine, maybe a little port and the sharing of stories.

It becomes pretty obvious while looking over the new route sheets at breakfast there are no flat routes to be had in Portugal. Today we will attempt to do another 2,000 meters over 100k.

There is a chill in the air this morning and we start with a monster descent off of the mountain. The first climb is to the highest point in all of Portugal, and from what I can gather while I huff and puff, that’s the only notable thing this mountain.

Not even the pleasant banter from my riding partners can eliminate my particular disgust with this heartless ascent. Although, the panting Irishman is still able to get in a couple of pretty good ones about hunger and duck balls.

The descent off the other side of this god forsaken mountain is a different matter. This is the most beautiful descent I have ever ridden. Ever. Anywhere. The skinny European roads sweep down past giant cows, wearing giant cowbell, twisting and turning into a picture perfect valley filled with white-washed houses with the distinctive terra-cotta roofs. This is the Portugal I want want to remember. Not the moonscape climbs or any of the suffering, but this little village. It is magical and everyone agrees.

I come across Shawna and Andy on a brief stretch of cobbles through the center of town. They are headed for the second climb of the day. Shawna is the triathlete of the group, often seen heading out on a run as we complete the ride of the day. At first I hate her for this, but she grows on me to the point where I actually cheer her post-ride exploits. Andy is the smiler. He is always in good cheer and ready to go. Going through town Shawna slows to chat with me, but Andy will have none of it. He wants to push on. Chatting will have to come later.

The second climb of the day starts gradual and stays that way. For the first time all week we can settle into a rhythm and have a conversation. My riding partner is the newlywed Andrea. I have never met anyone who can bitch like a sailor, but come off so pleasant. Her husband is a lucky man.

The switchbacks take us up and over our route over and over again. It is as close to bliss as I can get with my exhausted legs. At about 10k from the top we are pulled from the route and driven to the top. Today’s lunch is back in town and we need to be off the roads. I am partially grateful and partially bummed. Andy and Shawna just avoided getting swept. That Andy is a wise man, with a big smile.

Starting the day with a 22-plus kilometer descent and ending it along a stretch of cobbles into a tiny walled village where a poolside lunch buffet awaits, makes you admit that it doesn’t get much better than this.

I start the next morning attempting to shoot some photographs from the saddle and instead I double flat. In the shadows of the initial descent I crack a pothole about as hard as one can without being thrown from the bike.

The rear tire explodes immediately and I pull to the side of the road. Being a big man, I have experienced this many times and instinctively pull the wheel. But instead of reaching for my repair kit, I hold the rear wheel over my head. Within seconds the follow car pulls up and pops on a new one. Not only am I back on the road, but I am back on the road with a push from the mechanic. So pro. Unfortunately, about 45 seconds later I hear a scuffling noise from the front end and then the familiar KABOOM. I pull the wheel, raise it over my head and presto I have a new wheel again.

I try to chase back onto the front group, but they are flying down off this mountain somewhere out in front of me.

After a couple of brutal days in the mountains of Portugal a day spent pedaling along some rolling terrain is much appreciated.

During our coffee stop today a couple of riders are offered a little something extra for their coffee. They assume it will be Kahlua or some sweet liquore to add a little punch to their pick me up. What they get is a concoction somewhere between jet fuel and rubbing alcohol.

We are saved by the brave Chiquinho, the inGamba assistant mechanic, from countless stray dogs and I am eternally grateful for the slow-moving paceline.

I continue to be amazed at the ever changing Portugese landscape. It’s far more beautiful than the one I had envisioned in my head.

The day ends with a trip to the birthplace of Manuel, Joao’s dad, where we are served the most authentic and most delicious meal of the trip so far—including melon with cured meat, succulent steak and the most tender octopus I have ever wrapped my lips around. And even though I am relegated to the back of the bus, it is still a kick to be traveling on a professional cycling team bus from hotel to hotel.

I don’t think I can push my body any harder, or take another day in the saddle. But here comes another day on the road with inGamba. Just getting out of my plush bed inside the walled city of Marialva, Portugal is a challenge. My quads are tight and the calves are tender to the touch.

I shower and eat, trying to look calm while I assess the group. I am hoping they are feeling a little cooked too, but they all seem relaxed and ready to go. I want to hate them for this, but can’t.

We roll out, descending through the cobbled street of the walled city which we climbed the afternoon before.

It is an unreal scene: A group of cyclists riding state-of-the-art Pinarellos pedaling through a town where it appears time has stood still.

The group strings out along the river and I figure I better settle in for a long day of loneliness. But just as I resign myself to this fact the group comes together on the roll out of town. The most glorious double pace-line forms and we spend the rest of the day rolling through the amazing Portugese countryside as one unit. Stragglers off the back are brought back into the fold by the strong, young men on the inGamba payroll.

Except for the one giant descent where those of us who don’t go up so fast can’t help ourselves but to race to the bottom, the day is spent in conversation and relative ease. The final kilometers are spun away along the Duoro river.

We find ourselves spending the night at the Quinta da Pacheca winery, where we enjoy some delicious local port and the braver of us climb into a vat of grapes to help stomp grapes the old fashion way. It is a day of days.

Just two days left on this miraculous trip and I am forced to choose between a day in the saddle or a float down the Duoro River aboard a 40-foot yacht. The group is split down the middle, and as much as I am torn, my hamstrings place the final vote and I head for the river.

Of all the amazing bike riding skills I have witnessed this week, it is the bus driving of Luis Almeida which truly impresses. Watching him maneuver the Portuguese Cycling Federation bus out of the parking lot this morning is truly a spectacle.

The float down the Douro is definitely about as good of a recovery day as one can have. I finally succumb to the hum of the boat and the greatest nap in the history of naps falls upon me.

So one final day in the saddle. How do you make it memorable? You invite along a pack of Portuguese cyclicts.

From the gun, a paceline forms and the pace for the day is set at about 30k an hour, which to some might not be on the rivet, but almost everyone in the group has five or six tough days in their legs already. I try to find myself a nice little spot in the back and hide out. With the first 50k going by in a blur, I start to feel a little melancholy about the trip coming to an end.

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It’s a cliche, but the group has become a rolling family of sorts. We have started to understand each other’s idiosyncrasies and have learned to appreciate who we are as a group.

With the end drawing near, everyone starts to get a little frisky. I, of course, start talking shit, but when the group jumps, the fast kids go up the road and I can’t back up my smack and pop off the back like a bad seed.

I can see the group up the road motor-pacing behind the team car, but I end up stuck in no-man’s land. Luckily for me, the newlyweds come by and pick me up. And I find a nice spot behind the tattooed wonder, Ryan, and his wife. They drag me through the headwind to the end.

We finish our adventure at the Design Wine Hotel, on the border of Spain. There is one last spread prepared for us. Our ride bags our laid out one last time. We share stories from the road one last time. It is truly something amazing we have shared over the last seven days. The food, the wine, the open road. We have been pampered and watched over. Every need has been met. This has truly been the trip of a lifetime.

Let’s do it again.

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This post is dedicated to
Bruno Miguel Gomes Castanheira

Bruno worked for inGamba and passed shortly after the Portugal trip ended. Worked is really not the right word. He was one of the many people who made this trip special. He was always there with a smile and helping hand for those who were struggling to stay with the group. Although we didn’t understand a single thing the other person was saying due to language barriers, it did not stop us from talking. He was an incredibly expressive young man and strong as an ox. You will be missed, Bruno. But not forgotten.

My name is Scott and today I am declaring myself Element.ly’s Midwest Editor. I’m not sure I know what that means, but I love the way it sounds. Anyway, The Paris Review has one, so I’m pretty sure that it is a thing. I don’t know where you live, but here in the Midwest, we are a rugged folk. On a good day, we wake up and do two ice-bucket challenges before breakfast. And then we get on our bikes and head out onto endlessly flat, chip n’ sealed country roads where it is nothing but head wind, head wind, and more headwind: behind corn and soy our fields grow paradox and we are used to it. On an especially good day, we might get to see another cyclist and give them a nod as they pass and we judge their ride and the funny shape of their calves.

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We ride on trails, too. Where you live, they probably put public spaces at the tops of mountains of various sizes, but here we shove them all into the floodplains that line our slow, brown rivers. It affects the view, the number of bugs. Our climbs are short and steep and redundant, but we love them because they elevate the heart-rate and help us earn our gluten-free beer. As I write this, I know that riders on the work crew are daydreaming about berm contours on our local single-track and arguing online about the mysterious defacement of a log. On one side of the debate are those who say that if you don’t have 12” of travel, you shouldn’t be out there, and on the other side is no one because when you chainsaw a root that pisses you off, you melt into the night; you don’t show up in a forum to brag about it.

Here in the Midwest, the two coasts fit right around us, like the speakers in the tinny headphones we wear while mowing our massive lawns. Which is a way of saying this: don’t think we don’t know what’s going on out there or realize what we don’t have. But we’ve got all these places, too, these tiny landscapes that, when we drag our kids there, make my wife and me say to each other “you know, if this were in California, it would be world famous,” or at least in Sunset magazine or something. So these are some of the places I know about, and I hope I can do some of them justice here.

We started the Instagram feed here at Element.ly even before we launched our website. Over at WIRED, we started the Instagram feed before most people had even heard of the crazy app—back when it was easy to go from five followers to 50,000 relatively quickly.

Now Instagram is huge and finding a voice amongst all the noise is hard. But that’s fine. We still love photography and love sharing good work.

Because it’s Thursday, we wanted to take this opportunity to re-post some snappies you might have missed from our early days. If you like what you see, please follow along. Leave comments on our feed, let us know what you like and feel free to submit photos from your own outdoor adventures.

Here are a few lessons I learned while riding my bicycle across Portugal with inGamba earlier this month:

Cod is not universally loved by the Portuguese people.

Descending is for show and ascending is for dough.

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Not all wheels are the same in a paceline. But when the dust kicks up, any wheel will do.

Riding the cobbles makes you wonder how they race the cobbles.

Riding in a large group where everyone is wearing the same kit is cool.

Getting on a clean, well-tuned bike every morning is addictive.

A proper saddle and comfortable shoes are key.

Strawberry jam is an essential part of any breakfast.

Never judge a rider until you have tried to shake them off your wheel.

Skinny guys really do climb better.

The deal is in Oregon.

There are plenty of women in the world who can hammer your ass into the ground.

Most bald men look better with helmets on.

Melon and cured meat, served as an appetizer, is the bomb.

Not all red wines are created equal.

Olives go great with draft beer.

If you claim to be allergic to gluten, the Portuguese will bring you giant, amazing salads every day.

Someone else carrying your luggage is a luxury everyone should experience.

62 is the new 40.

It is possible to blow two tires and ruin both rims at the same time without crashing.

The second climb of the day is almost always less painful than the first.

Hanging on to the side of a car is way easier than climbing.

Eating tiny homemade sandwiches and treats is way better than energy bars and gels.

Sometimes it is nice to have a guide at the back and sometimes you wish he would get the fukk away from you.

Nine seats on a cycling team bus is great, if you are one of the nine.

Dating a triathlete should be an Olympic sport.

Sometimes you need to decide between the ride and the view. I prefer the ride. I can always buy a postcard.

The Portuguese people are some of the friendliest in the world. “Buen Dia.”

Sometimes you just have to take a spa day.

Steak sandwich for dessert is delicious.

It’s nice if your domestique is also your spouse.

Ordering coffee for a group of 15 cyclists is nearly impossible.

Comfortable shoes are the key to happiness.

The Irish really do know the dirtiest jokes.

Sometimes, if you want to go on a bike trip, you will have to follow it by kayaking with your wife.

Cauliflower pizza is way better than it sounds.

Apple executives are as smooth as you think they would be.

Tubulars are all they are cracked up to be.

If you’re having a rough day, sit at the back of the pack and when it’s your time to take a pull, pretend like there’s something wrong with your bike.

Riding fast is fun and getting shelled is not.

It’s always nice when the strong rider is willing to pull you home.

When someone starts to shake a champagne bottle, don’t just sit there. Run.

Osmo energy drink doesn’t really taste great. But boy is it a lifesaver.

“Eat before you are hungry and drink before you are thirsty,” really is great advice.

A luxury hotel is way better than a Motel 6.

The sun beats down on us and terrible humidity makes it worse as we crunch our way up a winding trail to the top of a volcano outside León, Nicaragua. We’re here because we’ve come to ride sheets of plywood down this hulking mound of cooled lava.

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Along side us are tourists from across the world and everyone is cursing the heaviness of the board and complaining about the jumpsuits we’ll have to wear when we slide down so that the volcanic rock doesn’t scrape our skin off like a cheese grater.

As we climb higher, the cursing stops as those who are out of shape suck wind and those who are fit embrace the challenge. The smell of sulfur washes over us and the wind picks up, tugging our boards back and forth like huge kites. But we hold on because the thought of dropping the board after climbing so far terrifies us.

At the top, our initial nervousness is replaced by fatigue as the guide tells us how this volcano, which is called Cerro Negro, is the only volcano in the world where volcano boarding is possible. We’re not sure if he’s right, but we’re too tired to question him.

Then he gives us the rules: 1. Do not open your mouth on the way down because rocks can break teeth. 2. Wear your goggles because rocks can blind you. 3. Once the slope goes from 30° to 45°, you are not allowed to brake because you will lose control and it will hurt. He says people have broken things but no one has died.

We settle ourselves onto the half-inch thick boards and grip the thin nylon rope that’s attached like reins. Sitting on the board puts us so low to the ground that we can’t see past the black lip of the volcano.

And then it’s on.

We dig in with our feet trying to steer as rocks rush under. The board heats with friction and we realize our mouths are still open. As we hit the ‘steep’ part, we pull our feet up high enough to just lightly skim the surface of the crumble and we fight every instinct to over correct. Another guide points a radar gun at us as we whoosh past and eventually slide to a stop. Fifteen seconds and it’s over.

Photos: Alex Washburn / Element.ly

The other week, my husband flipped over the handlebars of his mountain bike, landed on his head, and rode out of the woods with a concussion. He was wearing the POC Trabec Race Helmet I’d bought him a few months earlier, which shows that I know exactly what he needs.

He was already a fan of this helmet: it’s extremely lightweight and the little visor that’s meant to shield your eyes from the sun appears to have also protected his face from getting destroyed in an earlier wreck (He doesn’t crash as frequently as this post makes it sound, but sometimes bad luck comes in bunches). Now he’s alive with a functioning brain, so that’s a pretty good endorsement for the lid.

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His main symptom was short-term memory loss, which at the time was terrifying, but in retrospect was a gift: He acted so damn weird that I knew we should head to the emergency room. A CT scan came back fine. After a few days and lots of sleep, he was mostly recovered, although he’ll probably never remember the evening of the accident.

It’s a reminder to wear a quality helmet, of course. But this wreck also proves that even if a helmet sustains little visible damage—my husband’s POC had a patch of abrasion and a very small dent—the rider may still have a concussion. In fact, as Bicycling Magazine notes, he almost certainly does.

Since a concussion is such a common cycling injury, it’s worth learning about the symptoms in advance. Note that most people don’t lose consciousness; my husband never did. And when a rider rattles his brain, he might not be lucid enough to know that he should see a doctor. At that point, the helmet’s job is done. Then it’s up to us—riding buddies, friends, and family—to provide the next layer of protection, and steer each other down the path of recovery.