The Amazing Cindy Lew

I met Cindy Lewellen in the summer of 2009 during the Cascade Classic Stage Race in Bend, Oregon. I liked her immediately, sensing that behind her quiet demeanor and good-natured attitude, there was an adventurous, athletic woman who lived life according to her own rules. It might have been the monstrous BMW R1200GS motorcycle that she drove away that tipped me off. Lewellen was driving photo-moto for the first time ever that year and as we chatted over dinner about the thrills and spills (literally) of life on a motorcycle moving through a peloton, I remember hoping that our paths would cross again. I got my wish more than a year later when we worked together at the Cascade Classic as the only female photo-moto duo.

During my stay at her home in Bend that week I learned that Lewellen is not only a skilled motorcyclist (she rides dirt bikes, too), she’s also a talented runner and gifted cyclist with a penchant for going uphill in a hurry. Rest assured, you can find her on any given Rapha ride putting the nails in Slate Olson’s coffin up the storied gravel back roads of Portland’s west hills.

Lewellen is wicked smart and stunningly beautiful, so it shouldn’t be surprising to learn that she’s one of the gritty and elegant women that features in the photography for Rapha’s women’s line. Modest to a fault, she’ll cringe to read about herself this way, but the fact is that she embodies much of what is best about the glory and suffering of road riding: beauty blended with athletic grace, aggression balanced by introspection, competition tempered by camaraderie.

I was lucky enough to get her to take a few minutes to answer some questions about how to win a bike race without knowing it, the best bike shop in Melbourne, and what it’s like to ride solo across the country on a Ducati Monster S4R Testastretta.


When did you start riding motorcycles? What was your first bike? What was the hardest thing in the beginning?

I started riding motorbikes about eight years ago. I was dating a guy whose sole means of transportation was by moto and after a few trips to the market staring viewless at the back of his helmet I realized if there was any chance the relationship was going to work I’d have to learn to ride. Given my love for self-propelled bikes I didn’t expect to enjoy it but took the Motorcycle Safety Course, finished top in my class and had a brand-new Moto Guzzi Breva 750 delivered to my front door the next day. Needless to say I was hooked. The hardest thing for me was getting the brake/clutch/throttle timing down. Balance, bike handling and picking lines came naturally from road and mountain biking but until shifting and braking became instinctual it was a lot to think about at once. Your mind can never wander on a motorbike. Maybe that’s one of the reasons I like it so much.

I heard you rode a motorcycle across the country to deliver it to the buyer on the east coast. What bike was that and why were you selling it? How long did the trip take? Would you do it again? Any stories from that trip that particularly stand out as memorable?

Yeah, a couple years ago I decided to sell my sexy and wicked-fast Ducati Monster S4R Testastretta to a friend in New York who was going through a mid-life crisis. I had a lot of fun on that bike but it really wanted to be on a track or ridden fast and that’s not my style of riding. I like the twisties.

I looked into shipping it then got a wild hair that hand-delivering it would be fun. I was in-between freelance projects at the time so just gave myself a few days to loosely map out a route and get the bike in order then set off. My course was determined by the cities I’d wanted to visit and ‘epic’ roads/twisties I’d heard about and wanted to ride.

The trip went off without a hitch, the only close call happened in Knoxville, Tennessee, where I was accosted and threatened by the town crazy while searching for my morning espresso. I found it ironic that that incident could have been my obit instead of dying more predictably on my motorbike. The journey took two weeks. When I arrived in NYC I learned my friend the buyer, who’d recently welcomed his first child with his wife–one of my best friends—still hadn’t found the “proper time” to tell her he was buying my bike and now they were in France for L’Etape. I was instructed to drop the bike off at a friend’s house , I flew back to Portland and have never asked when and how he finally told her. But they’re still happily married and his angelic wife and I are still friends and he now has a sweet Ducati on which to live out his mid-life crisis so all is well. It was lonely at times but sure I’d do it again.

What’s the hardest part about riding photo moto? What’s your favorite part?

Photo moto support is by far the most stressful motorbike situation I’ve experienced. Safely and smoothly navigating a 500 lb. bike with a photographer dangling off the back as you’re communicating with and dodging Comm cars, moto officials and other photo-moto bikes and support vehicles while ultimately concerned for the safety of the racers is a lot to handle at once. My favorite part is taking off my sweaty boots and helmet at the end of the day. But riding around in the blistering sun watching boys race bikes in lycra with you, Heidi, takes a close second.

What’s the hairiest situation you’ve ever been in while driving photo-moto during a race?

What makes me most nervous is when the peloton drifts into the moto’s line as we’re trying to pass from behind. It can happen so quickly and suddenly you’re surrounded by riders on all sides, so close I swear I can feel them breathing down my leathers. Hold your line hold your line hold your line…. How about my most embarrassing moment when the photographer mistook my shouts of “no no no!” with “go go go!” and swung his leg over the seat with only one of my hands on the bars, sending the bike crashing to the ground just as the peloton rode by. Nice.


I hear you’re a big runner. What’s your favorite distance? Do you ever race?

I grew up a swimmer then burned out and started running for fun in college, eventually racing marathons and half-marathons. I don’t do those anymore; I’m wiser now. Half-marathons were my favorite because I didn’t have to train much for them. But I do love running. I’ll always appreciate the simplicity and efficiency of it.

How and when did you start cycling?

Bicycles have always been in my life in one form or another. I had very active parents and at an early age they had me and my sisters on bikes and they’d go everywhere with us. We’d pile in the station wagon and head out to Hagg Lake for a family spin. It’s also how we got to and from the local swimming pool multiple times a day. In my 20s I ran a lot and mountain biked then lived in Amsterdam where the bike was my means of transportation. I didn’t know anyone there who cycled for sport and it didn’t dawn on me take it up given I was already on a bike every day. When I moved back to the States I started cycling for triathlons however still preferred the singletrack with my dog. It wasn’t until my dog got too old to run that I started spending more time on a road bike. That was about five years ago.

Which bikes are in your stable? Which is your favorite?

I keep my Klein Palomino dualie in Bend where the trails are worthy, and in Portland my ancient Klein Q-Carbon road bike and Gary Fisher hardtail are collecting dust in the basement along with my Giant TCR Advanced 2 that I haven’t been able to bring myself to ride since getting my Moots. An Igleheart ‘cross frame JD loaned me will soon be replaced by a Moots Psychlo X to keep my beloved Moots Vamoots CR company. Now that I’ve tasted titanium I can’t go back.

You’re a born climber and, while I hate your guts for that, it’s pretty amazing to watch. What is it about climbing that you love?

Yes, I do love to climb and genetics and my running background probably have something to do with it. Apparently I’m into pain, sustained efforts, and the potential payoff of a fantastic view from the top. But what goes up must come down. I enjoy descending as much as climbing.

You took a trip to Australia a few months ago to ride. How did that go? How long were you there and how many miles did you put in? See any amazing roads or country that we shouldn’t miss if we make if over that way?

Yes I escaped dreary Portland in December and headed south to visit an old colleague and his wife in Melbourne over the holidays. I was connected with the owner of Northside Wheelers–Melbourne’s first Rapha dealer and the coolest bike shop I’ve ever set foot in–to show me some rides during my stay. I rode with Malachi and his team, Sole Devotion, the two weeks I was in Melbourne and got a great sense of the city and its crazy-popular cycling scene, which felt five times the size of ours in Portland. Granted we don’t have a Beach Road on which every cyclist can (and does) flaunt their rides, wares and egos, but I’ve never seen so many people on bikes! The team then invited me to join them in Adelaide to watch and ride the Tour Down Under. Seemed like an opportunity I couldn’t refuse so arranged to stay another two weeks then spent a week in Tasmania doing some rainy-weather riding before meeting the guys in Adelaide for the Tour. Everything about Adelaide was stellar—the riding, the racing, the hills, the beach, the food, the coffee, my riding mates. It was the perfect riding holiday. I wasn’t consistent with the Garmin and don’t keep a log so can’t tell you how many miles I put in!

You ride with the Portland Rapha crew a lot. How competitive do you get on group rides? What’s your favorite part of group rides?

Yes the Portland-based Rapha staff and Conti crew are very kind to let me ride with them. Maybe they just invite me along as an excuse to go slow, I don’t know. But I’m grateful and couldn’t ask for better training partners and mentors. Not to mention they usually keep me laughing so much I forget how much I’m suffering. I ride hard when I’m with the Rapha crew so they don’t have to wait for me. I ride hard on big group rides to get away from the idiots. I ride hard when I’m with women if we decide the ride will be hard. Am I out to smash people on group rides? No. I’m only competitive with myself. I like group rides when they take me on roads or gravel I’ve never been. I like that four hours in the saddle with friends goes much faster than four hours alone with an iPod. I really like the coffee breaks and conversation.

You entered one of the weekly Mt Tabor races in Portland last year and won. That was your first race, right? What was it like to win? How did it go down? Do you plan to do anymore racing?

Yes, I won my first race on Tabor but didn’t realize it at the time. I mistook stragglers from another category in front of me at the finish with women from my group. I started my ride home after the race and it wasn’t until some women in my race caught up to me and started congratulating me that I realized I’d won. I got second in my second Tabor race. Now they have my number. I’ve done three road races this year and I’m enjoying the strategy involved. It’s hard for me to be patient and sit in and not do a lot of work but I’m pretty sure that’s not how to win races. However I won my last race so maybe I’m staring to figure it out. Next up is the East Coast Rapha Gentlemen’s race. I’m honored to be riding for the Moots team.

You dabbled in Cyclocross last fall. What did you think?

Yes, I did a little dabbling and the dabbling I did do was really fun. I won my first race and did a weekly then got injured and was traveling which put me out for the rest of the season. I have to admit my biggest fear in ‘cross is the (Cross Crusade) crowds. The thought of racing in front of all those people makes me want to puke. I’ll have to get over that.


You’ve modeled for two seasons of the women’s line – once in Italy and once in Palm Springs. What are those shoots like? What’s your favorite part of that work?

I wouldn’t call it modeling but yes I’m one of the riders Rapha has used in their photo shoots and I’m pretty sure it’s just because I’m the only woman Slate knows who rides a bike and fits their sample size.

The first shoot in Siracusa, Italy, was a fun, new experience for all of us. I’ve been to Sicily a couple times but not to the part of the island where we shot. It was gorgeous. The weather wasn’t as cooperative as hoped so we utilized the time off the bikes cooking and eating some incredible Italian food.

In Siracusa I had my first crash on a road bike that sent me to the hospital with blood spurting from my head. It looked much worse than it was but I think I gave poor Simon a heart attack (and a good story). A few stitches later and I was ready to roll. The second shoot last November in Palm Springs took the definition of a shoot to a new level. All us riders from Portland and LA knew each other and of course the talented Ben Ingham was back to create more stories both from .

Our 4:30a wake-up calls to catch golden hour didn’t always feel so good (and I don’t think we ever actually caught it), nor did that second ride of the day when my legs didn’t have anything left, but it’s hard to complain about long days in the saddle in stunning locations like Joshua Tree and the Salton sea with people you love to ride bikes with. And shoot bikes with.

What’s your favorite piece in the women’s line? Why?

Rapha’s Women’s Shorts are the bomb. The cut and chamois are the most comfortable I’ve ever worn and – don’t worry ladies – they’re working on the tan lines. My next favorite piece would have to be the Women’s Softshell Jacket. Before buying one I assumed it would be too warm since I tend to ride hot but with the arm pit vents unzipped and worn only with a short or long-sleeved base layer underneath (not a jersey) I’ve never been too warm or stayed so dry. The back pockets are enormous and the “storm tail” keeps my bum dry when my fender’s not working….err…on. It’s also a simple and stylish jacket to wear off the bike.