Five Days on the Oregon Trail (Gravel Grinder)

Five Days on the Oregon Trail (Gravel Grinder)

Five Days on the Oregon Trail (Gravel Grinder)

Is this the future of stage races in North America?

Words by: Chris Bagg
Photos by: Wil Matthews

For members of a certain slice of Generation X and the Millenials, the phrase “You Have Died of dysentery” carries a Proustian freight, a portal to an early, important phase of life. Oregon Trail, an early video game that was ubiquitous in elementary schools in the late 1980s and early 1990s, focused on your efforts to transport your family (often with disastrous results) from Independence, Missouri to the as-of-yet unincorporated promised land of Oregon, where—if you could survive the journey—a homestead awaited you along with the better life a piece of land leant. In the real world, displaying an early stroke of gender equality, women (scandalous!) could also secure a plot of land, making the trip twice as valuable for families, as long as you were comfortable wagering the lives of your children. The video game required poorly-rendered bison-hunting skills, which is mostly what this particular pioneer recalls, and more often than not your wagon would sink in the Snake River, or your bison meat would spoil and your family would die of dysentery (see above). The late 80s and early 90s were a period of relative freedom for children: most adults thought that grim educational games were just fine, as long as we stayed away from DOOM. Is it a scar that most of my generation associate dysentery with glue-scented elementary classrooms, or is that fact simply a badge of honor?

For Chad Sperry, race promoter of the Oregon Trail Gravel Grinder (OTGG from here on out, please), a five-day stage race/traveling caravan/nomadic endeavor, the experience of the video game must have been a central one to his childhood. Sperry’s event company, Breakaway Promotions, puts on many high profile events on the gravel calendar, including the always great Lost and Found in early June, but in his words, Oregon Trail is “the crown jewel of our events.” Sperry and his crew work most of the year to ensure OTGG unfolds smoothly for its participants, which is an endeavor of no small magnitude. Each morning participants pack their non-racing equipment and their into one of those ubiquitous black and yellow plastic tubs and drop it off with one of Sperry’s drivers. For a small extra fee you get an event-supplied tent that you simply leave standing when you head to the start line; one of Sperry’s employees will come along and pack the tent for you. All you have to do (no small task) is complete each of the stages and arrive at Bike Camp, where you will find your tub and your tent waiting for you. The entire race describes a giant loop, beginning in Sisters, Oregon, crossing the Cascade Range to the west before doubling back, crossing the mountains again (more on that particular challenge later) before winding back to the north and concluding in the peaks that loom above Sisters. Each day is fully catered, breakfast and dinner served at camp, with aid stations along the way and sandwiches available at the finish.

Oregon Trail Gravel Grinder Logistics Tent Camping, moving gear from stage to stage, riders camping in their tents, and feeding the riders during a 5 day stage race

Race directors, these days, often have a tough decision to make: put on participatory events that attract a wide audience but don’t offer much to the hardcore racer, or mount races that focus primarily on the crowd that knows their functional threshold power to the nearest decimal point. Sperry manages to make you a cake and let you eat it, too, as OTGG draws competitive racers and those who simply want to challenge themselves alike. And in the evening those distinctions disappear, as everyone gathers around cornhole courts and mobile firepits and cups of free beer (yup!) to talk about how difficult/amazing/challenging/epic/beautiful that particular stage was. This was my first attempt at OTGG, and I’ll certainly be back. If you’re interested in attending this glorious event, which I believe is a sign of races to come, you can read a stage-by-stage description below.

Oregon Trail Gravel Grinder Stage Race Post Race relaxing and recovery, with group activities

Stage One - No One Said It Was Easy

You ever hear the maxim to start small? Apparently, Sperry hasn’t. If Stage Four weren’t such a monster, Stage One would be the queen stage of this race. As it is, this stage, if we’re gonna stick with the royalty metaphor, is an impertinent princess looking to bump off her mom so she can be the new monarch. Stage one is very hard, as opposed to the “very, very hard” of Stage Four. Both distances, Settlers and Pioneers, are nothing to sneeze at, covering 66 and 75 miles, respectively, but the pioneers get an extra 11 mile climb that adds 2200 feet of climbing to the menu. You’ll also experience a sandy section early in the stage that can either be sheer joy (we got some rain the night before, which turned this section into a fun rollercoaster) or soul-sucking (if it’s bone dry in the days before the race, prepare yourself for plenty of hike-a-bike), but either way it’s a challenging appetizer to your five days of riding. After the sand you’ll descend through loose and rocky terrain as the climate shifts from high desert to rainforest. If you’re a good mountain biker, you’ll love this section. The rest of us? Remember to stay off your brakes and look where you want to go. Today’s stage rewards big tires, low pressures, and mental fortitude, especially if you’re doing the Pioneer version. That second monster climb can try your patience, so stop looking for the end of the climb and enjoy the views, which are dramatic—very few people will get to see what you’re getting to see today. 

Oregon Trail Gravel Grinder. Stage one gravel bike ride, race director Chad Sperry, Sarah Max, Pacific Northwest

One really nice feature of the OTGG is that the timing finish is usually several miles from Bike Camp, so you finish up this stage at 58 and 66 miles, respectively, for the Settlers and Pioneers. It’s a welcome break to be able to coast into camp on Day One, wondering about your life choices. Camp that night is made at the McKenzie Track, a beautiful composite track in the relative middle of nowhere, and few things this week will be as striking to you as turning into the facility and seeing a small city of tents set up in the track’s infield. If you did spend a significant portion of the day wondering about your life choices, that evening will help, as you experience Bike Camp for the first time, eating and drinking with your friends in a small copse of trackside trees. Debating one’s life choices goes down easier with empathy, which is perhaps a wordier way of saying that misery loves company.

Stage 1 Pioneers Route

Oregon Trail Gravel Grinder 2023 Stage 1 Pioneers Route

Stage 1 Settlers Route

Oregon Trail Gravel Grinder 2023 Stage 1 Settlers Route

Stage Two - Westside Connection

A truism about bike racing states “short stages are to be approached warily.” Or, rather, I just invented that truism, but I believe other cyclists would stand by it. Stage two is short: 38 and 50 miles of racing contained within 49 and 62 total miles, respectively, for the Settlers and Pioneers. Side note: how many times will the word “respectively” show up in this article? Ten times? One hundred times? No time to wonder. Onward. Sperry makes up for that shortness with a 16-mile climb right from the gun that rises 3,300 feet. Your consolation? You get half of the climbing done in the first third of the stage’s distance! Don’t you feel better? The Settlers, I would argue, don’t have it much easier today: you get both major climbs in 12 fewer miles of racing, which only means the aggressive riders will try even harder to tear your legs off. Still, this stage is probably the most enjoyable in terms of the road surface, which is classic Gucci Gravel in most spots, and Sperry has a little surprise for you: the Aufderheide Scenic Bikeway that provides the meat inside today’s gravel bread slices (yikes that metaphor is tortured—no matter). The Aufderheide rolls gently along for almost ten miles on both courses, giving you a welcome break from the banging of yesterday. You do finish with another climb, a short, sharp gravel pitch of about two-and-a-half miles. Your prize, following the timing finish, is a literally breathtaking paved descent into the town of Oakridge for your two-night stay at Greenwaters Park, which perches on the edge of the Willamette River. That night you will soak your legs in the headwaters of Oregon’s second-most-famous river and continue to debate those life choices with your friends.
2023 Oregon Trail Gravel Grinder Greenwater River Park Pacific Northwest

Stage 2 Pioneers Route

2023 Oregon Trail Gravel Grinder Route 2 Pioneers Routes

Stage 2 Settlers Route

2023 Oregon Trail Gravel Grinder Stage 2 Settlers Route

Stage Three - Straight Up, and Down in a Hole

Stage Three shows off the kind of thinking that makes OTGG interesting and innovative. Borrowing from both road racing and mountain biking, Stage Three features a long, friendly neutral section as you circumnavigate Hills Creek Lake, the source of the…mighty (mighty may not be the right word…adequate?) Willamette. Stage three is the shortest of all five days at OTGG, with a commensurate amount of racing. The neutral section was, for almost the first time in this particular racer’s career, actually neutral. After two days of hard racing, with a queen stage to come on Day Four, the peloton actually behaved itself. Smiles were given and received. Sperry handles the racing on Stage Three in two enduro-style segments, one uphill and one down. After the gentle, friendly rollout, everyone came to a stop and then left in groups: the top 20 men, top 20 women, and then the rest of the field. The uphill segment didn’t start for another two or three miles, so the leisurely pace continued. Once we crossed the timing mat and the road tipped uphill, however, leisure no longer described anything. The Settlers field skips these two timed segments, instead getting a lovely ride around the lake, but for anyone racing the Pioneer field, the next seven miles probably make for the hardest of the week. The segment starts gently enough, stair stepping through the woods, but the final two miles are brutish, averaging 9% and hitting max grades of over 11%. All told the climb averages 6% over seven miles and a maximum of 15%. Bring a low gear, is all the advice I can offer. Once you’ve finished the uphill time trial, you have a few minutes to recover before plunging off the backside of the mountain, dropping 10 miles at an average descent of 6%. My advice for this section? Take some air out of your tires before you’re given the green light to start. Stage winner Carl Decker (Giant) opted for “Eh, something in the low 20s, I think,” before he sprinted away from the start arch to a few raised eyebrows. “Do we all have to start that fast?” I heard one rider mutter in the ironic tone of voice many present-day cyclists adopt. Decker turned out to have the final say, claiming victory by one slim second. Respect your elders, kids. There’s a reason they’re still around.
2023 Oregon Trail Gravel Grinder Bike Race Greenwater River Park Pacific Northwest Bicycle Gravel Ride
After you’ve made it safely down the mountain, all that’s left that day is another easy spin back to Greenwaters Park, where you get to repeat last night’s festivities, free from the stress of relocating to a new location. Spirits were muted the evening of day three, as athletes piled plates high in anticipation of Stage Four, which everyone knew would be something else indeed.

Stage 3 Pioneers Route

2023 Oregon Trail Gravel Grinder Stage 3 Pioneers Route Stage 3 Settlers Route

2023 Oregon Trail Gravel Grinder Stage 3 Settlers Route

Stage Four - Crossing Over

On the morning of stage four, a palpable reserve settled over the camp in Oakridge. Not dread, not exactly, but the quiet focus of nearly 400 people who knew they were about to do something very difficult. Is this what Independence, Missouri felt like in 1836? I jest, of course, but humans are drawn to large, difficult things, and in today’s latter days maybe this is how we access those feelings, for those of us who aren’t astronauts, solo-crossing sailors, or mountaineers. The Settlers almost exclusively rolled out early, at 7am, to get a head start on the day. The Pioneers (and one lonely Settler—props) left at 8:30, and, as had been the case most mornings, kept the pace restrained until the road tipped uphill at the 12 mile mark, where the first climb of the day began: a 12 mile, 6% monster with maximum gradients of over 15%. The settlers carve about 9 miles off the Pioneer stage and subtract around 3,300 feet, for those of you keeping track at home.

2023 Oregon Trail Gravel Grinder Stage 4 Bike Race Gravel Bicycle Ride Pacific Northwest

How does one do justice to a stage like this? 10,000 feet of climbing; water crossings; a stretch of course from the original Oregon Trail that has never been worked on since the 19th century (and feels like it); this year there was hail and wind; sand; vistas that few people have been privileged to see. If riding a bike in difficult settings is your thing, Stage Four is why you signed up for this race in the first place. The fact that it comes after three days of hard riding only makes it sweeter (once you have finished, that is). You cross the Cascades for the second time, seeing the climate switch back from loam and pine to dust and sage. If the rain hadn’t been so worrisome, the smell of the high desert unlocked by falling water alone would have informed you that you’re doing something amazing and epic. I’ll let the pictures and the ride files speak for themselves, now, since there isn’t too much more to say. You will remember this stage, both for the literal high points and the metaphorical lows, and tomorrow will seem slightly easier, having gotten this one out of the way.

Stage 4 Pioneers Route

2023 Oregon Trail Gravel Grinder Stage 4 Pioneers Route

Stage 4 Settlers Route

2023 Oregon Trail Gravel Grinder Stage 4 Settlers Route

Stage Five - Homeward Bound

If Stage Four featured quiet at the start, Stage Five felt like a collective sigh of relief. No one thought today would be easy, per se, but the final stage has significant neutral bumpers, shrinking the 85 mile ride to 58 miles of racing. Your prize upon finishing the timed section is “the most beautiful finish line in North America,” on the shores of Big Three Creek Lake, which hunkers in the shadow of Broken Top mountain. After cokes and Rice Krispie treats and cookies you get an amazing 15 mile descent back to Sisters, Oregon, ideally chatting with your new friends about what you’ve achieved over the past five days. First, though, you do need to navigate some bumpy, loose, and arrhythmic sections of trail between La Pine, where the race starts, and the aforementioned finish line. You climb up to the shoulders of Mt. Bachelor, and this particular rider thoroughly enjoyed riding the trails of Virginia Meissner Sno-Park, where he’d only cross-country skied before. You’ll experience amazing and fast paved sections, gnarly and fast double-track roads, and then a final climb to the lake. Apparently, some years, riders have gone into the lake, but this year’s cooler temps meant feet got dipped in, but no bodies as far as I could see. A few drones buzzed overhead, collecting video, and volunteers wandered around, making sure everyone was OK. Riders gathered themselves, put on wind jackets, and coasted down to Sisters, completing a 350- or 280-mile multi-day epic during which no one literally died of dysentery.

Stage 5 Routes - Pioneer and Settler

2023 Oregon Trail Gravel Grinder Stage 5 Routes - Both Settler and Pioneer

Should You Stay Or Should You Go?

2023 Oregon Trail Gravel Grinder Finisher Swag T-shirt flask patch

2023 Oregon Trail Gravel Grinder Did Not Finish Swag Pack

OTGG is hard, at both distances. The race is five days long, but you will need a day on either side for preparation and then for gathering yourself afterward. Your author struggled, a small series of mistakes and circumstances contributing to his (very much self-selected) adversity. There were two occasions when I very clearly considered giving up (I really wanted a tee shirt that said I had died of dysentery), but a month later, writing this article, I am so glad I persevered. Sperry says that his crew looks forward to this event more than any other on the calendar, and I can see why. One-day events provide racing fireworks, but for the staff a one-day is little more than a gig. The glory of OTGG is that everyone bonds during the five days of racing. You get to know the timing staff, the moto riders, the cooks and caterers, the announcers and media folk, the bike camp logisticians (Colleen, you are amazing), and Sperry himself, whom you can find doing dirty work everywhere. Does this sound sentimental? Does this sound, dare I say it, participatory? Maybe so, but OTGG couples the joys of participatory events with hard-knuckled racing. On both the open men’s and women’s side, the monster Stage Four came down to a sprint finish after three brutal days of racing, and the final podia looked like this in the Pioneer race: 

Open Women

  1. Evelyn Dong (Juliana) 18:32:45
  2. Stella Hobbs 18:58:09
  3. Kaysee Armstrong (Juliana) 19:04:35

Open Men

  1. Michael Van Den Ham (Giant x Easton) 16:06:49
  2. Cory Wallace (KONA Adventure Team) 16:17:12
  3. Matthew Bird (Cervelo x Pedla) 16:44:30

What I will remember from this race, other than the brutal riding and the huge vistas, are the moments in bike camp sitting with friends, waiting in the shower lines (mobile shower trailers follow the race each day, filling up giant terrifying bladders of gray water at each stop), chatting with the other Chad (of the glorious Autobahn Coffee), tossing cornhole bags, and eating, eating, eating. If you like to race (or not race) your bike, linger in the amazing outdoors of the Pacific Northwest in early summer, and take part in something bigger than your own personal ambitions, you should strike out on the Oregon Trail—who knows what you will learn about yourself along the way, and no virtual bison will be harmed.

2023 Oregon Trail Gravel Grinder

N.B. The 2024 course, while not released, will head in the clockwise direction next summer, touching many of the same locations but not in exactly the same way. Please see for upcoming details.

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