Back Discover more Shimano

Story by Kurt Gensheimer

Photos by Brett Rothmeyer

If there’s an indicator you’re getting old as a writer, it’s when a friend calls you to pen a nostalgia piece about a bike ride you both did together back in college. It would have been easy enough to pass on most other assignments, but the pull of a place like Bloomington, Indiana, and the legend of the Hilly Hundred bike ride was irresistible.

So I set the reality of advancing age aside, figured out how to ride a road bike again and returned to the pastoral hills of southern Indiana to experience “The Hilly” for the first time in more than two decades. I had fond memories from that time, but as I hung up the phone, I had a pang of doubt…would the old college town and Hilly Hundred really still be as legendary as we remember it?

Celebrating 55 years in existence, the Hilly Hundred is a staple of fall riding in the Midwest, attracting thousands of cyclists for two, 50-mile days on some of the best cycling roads in the US. It’s organized by the Central Indiana Bicycling Association (CIBA), a non-profit organization and one of the largest cycling clubs in the country, offering 600 rides yearly. The Hilly Hundred is a CIBA fundraiser and one of the organization’s two annual “signature” rides. The Hilly has risen to prominence over the last five decades, earning accolades like “Best Overall Event” and “Longest Running Event” from Bicycling Magazine.

Despite Indiana’s reputation of pancake flatness, the southern half of the Hoosier state avoided Ice Age glaciers, thus retaining plenty of geographical relief. Although most climbs in the region are no more than 500 vertical feet, some of the climbs are painfully steep, approaching 25 degrees in pitch.

I arrived in Indianapolis a couple days before the event and met up with my old college comrade, Adam Mahomed, who still lives in the city. We went for a warm-up ride along the Monon Trail, through Broad Ripple and out to Crown Hill Cemetery with its sweeping views of downtown Indy.

At the top of Crown Hill, we encountered a guy in his late 50s with scraggly, white hair. He wore a blue bandanna in lieu of a helmet, tennis shoes instead of SPDs and a Hoosiers sweatshirt tied around the handlebars of his 25 year-old GT Aggressor mountain bike and was knocking out hill repeats like a boss. He glanced up in a panting sweat to see us wearing our stylish Lycra, pedaling bicycles made of composites, titanium and electrified shifting. He was completely nonplussed by our appearance, and once he regained stable breathing, he went into friendly Midwestern conversation.

“You guys doing the Hilly Hundred this weekend?”

During the first ride on my first day back in Indiana in nearly 15 years, the first person we encountered riding a beat up old mountain bike in street clothes was training for the Hilly. If there’s any indicator the event is an institution of Midwestern cycling, this guy’s appearance said it all. Before we could even respond to his question with a yes, he kept on. “I’ll be there with some friends from Florida. It’s the only ride I can think of that has fried chicken at the lunch stop. And there’s a reason why they put the porta-johns on the side of the road three miles after lunch!”

After a laugh, the one-way conversation continued, including lopsided talk about the breakfast stop donuts, the afternoon ice cream and the late-ride beers. It seemed this guy was only training so he could eat, which I guess is as good of a reason as any. The interaction made memories rush back of my Hilly Hundred experiences as an undergraduate at Indiana University and the annual tradition of poaching the ride as a poor college student. We already knew the route from training year round for the Little 500 bicycle race on the hundreds of miles of quiet country roads surrounding Bloomington. We’d always manage to sneak a few pieces of chicken, donuts and ice cream down our gullets in the process.

Aside from the ride and the fried chicken, the Hilly was known for its massive event expo, where this aforementioned poor college student got blowout deals on cycling gear from helmets and shoes to jerseys and insulated tights for training in the bitter cold Bloomington winters. The bike expo also came in handy because some years the Hilly’s riding conditions required new gear to endure the biting winds, driving rain and occasional snow of late October.

The Hilly was also legendary for how many riders showed up, thousands of riders of all ages, nationalities and fitness levels. And the bicycles people rode were as diverse as the riders, with everything from tandems, recumbents and knobby-tire mountain bikes to old beat up 10-speeds from the early 1970s, oddball time trial bikes with 24-inch front wheels and high zoot speedsters made of unobtanium. If it had two wheels, or sometimes even three, and you could pedal it, you’d see it at the Hilly. I remembered on climbs like Bean Blossom, Mount Tabor and Stinesville, there’d be throngs of riders pushing their bikes uphill, leaving us college kids to pinball back and forth in our big chainrings around dozens of temporary pedestrians as they huffed and puffed uphill on foot. But more than anything, what sticks out in my mind about the Hilly Hundred was the incredibly beautiful rolling hills of southern Indiana and the hundreds of miles of roads perfect for cycling amidst brilliant fall colors. “I hope we aren’t jaded by nostalgia, man,” said Adam to me on our drive south from Indy to Bloomington. “I mean, I just hope we aren’t remembering things to be better than they actually are.”

For most people, including myself, the glory days of life were the first days of freedom as a college student, away from the grips of parental supervision. But that glorious memory of freedom is often masked by the realities we chose to forget–namely that annoying, slovenly roommate, the bank account balance a burrito away from zero, the gross cafeteria food and the damp, bone-chilling Midwest weather that made training long hours on bikes miserable at times.

Adam and I went for a campus cruise, riding past the ornate limestone architecture of the university, the hundreds of students marching back uphill to McNutt dorm from the business school. We rode a lap on the cinder track of Bill Armstrong Stadium, the site of the iconic Little 500. We coasted through the arboretum enroute to the Ernie Pyle School of Journalism where my writing career was born. Cruising campus felt like pedaling through a time portal back to 1997.

Despite the changes in B-town over the last 25 years, namely a slew of new massive university buildings, high end apartment complexes downtown, much appreciated bike lanes and a pedestrian-only Kirkwood Street, just as much is still the same. A born-again Christian still stands on the street corner with a PA system preaching the gospel and handing out bibles. A dirty old homeless guy is still posted up outside the city library on Kirkwood arguing with himself (probably the same guy). John Mellencamp still plays daily on WTTS radio. Beat poet wannabes still wax poetic outside Soma Coffeehouse. The Malibu Grill still looks exactly like it did when I worked there at the end of the last millennium. Little Zagreb’s still fills the air with the same salivating steak smells, and the Village Deli features the same menu it did in 1997.

And just like the old days, we had one too many drinks at Nick’s on Friday night and got a real late start Saturday morning. By the time we arrived at Ellettsville High School where the Hilly started, virtually everyone was already out on course. Adam and I were way off the back, so in honor of the old days, we threw down the hammer with reckless abandon to make it for donuts in Stinesville before the first aid station closed.

Rolling into Stinesville for the first time in decades reminded me of how unique this little, rural hamlet really is. Set at the foot of a steep hill with two winding roads out of town and Victorian-era buildings dating back to the 1860s, Stinesville has a European feel–it’s a town that gave birth to the limestone quarrying industry of Indiana and the term that cult cyclist aficionados across the country are familiar with, Cutters. The native oolitic limestone that came from Stinesville and the Bloomington region was not only used to build the infrastructure of Indiana University, but the stone also made its way into monoliths like the Empire State Building and the Pentagon.

We caught the tail end of the donuts in Stinesville before heading back out on the road through Mount Tabor and north to Paragon Road, dodging one dead opossum in the tarmac after another. We were still off the back and kept the big ring hammer down, averaging close to 25 mph, much to Adam’s displeasure, looking over at me with concern. “Hey man, if we don’t slow down I’m going to completely lock up.”

The nostalgic enthusiasm finally surpassed our lack of fitness, so we backed off the throttle, grabbed some fried chicken at the lunch stop and cruised south on Old State Route 37 through Morgan Monroe State Forest. As we approached the top of the climb after weaving through a few walking cyclists, a bagpiper dressed in full Scottish regalia came into view. I pulled over on the side of the perfectly paved road, basked in the sounds of my ancestral roots, and took in the brilliant reds, oranges, yellows and greens on an uncommonly warm late October day. I heard some singing in the distance and saw an older balding guy with a giant white mustache sporting a NASCAR tank top and chest hair billowing forth, paired with nylon basketball shorts, hammering no-handed with no helmet through the forest on an old Haro Escape like Dave Stoller piloting his bright red Masi in Breaking Away. Only the Hilly Hundred could deliver this oddity.

We jammed along Chambers Pike, down to Bottom Road where we used to do sprint intervals on our coaster brake Little 500 Roadmasters, and made a right through the Maple Grove Road Rural Historic District, one of the earliest settlements in Indiana and the first Rural Historic District in the state, with miles of dry-laid stone walls, homesteads and the Daniel Stout house built in 1828, the oldest building in Monroe County. Maple Grove Road is also famous for its three “camel humps” that smashed our hairy, unshaven legs into submission at the end of the first day.

The second day we got an earlier start to be more in the mix of the Hilly experience. We chose to ride from the house of our hosts, former professional cyclist and Little 500 alumni Ryan Knapp and his wife Rachel. The pair live at the top of a hill next to the equally steep and notoriously painful Boltinghouse Road. It was only two miles from the Sunday route, but in the back of our minds we knew the 25-percent grade up the driveway to finish was going to hurt more than anything experienced on the Hilly.

After climbing Robinson Road, we turned onto Shilo Road, one of my favorite sections of the entire weekend. Shilo has a distinct rollercoaster feel, hauling mass in the big ring, undulating up and down through a deep canopy of forest with slightly banked corners and broken bits of asphalt to keep handling skills sharp. Shilo delivered us down and over to the legendary Bean Blossom Road climb into Morgan Monroe State Forest where more than a couple riders took it on foot. After overlapping some of the course from Saturday, and cresting the short but incredibly steep Mount Tabor climb, another popular bit for walking, we rode through Stinesville once again, then onto Ellettsville and made our way back to Bloomington on the west side of town.

I always remembered the west side of Bloomington as hardman country, and my favorite zone to ride as it was true adventure road riding. The roads were beat up with wheel-eating potholes and bits of decomposed asphalt that felt like gravel, the hills were relentlessly undulating, suicide squirrels aimed for your wheels, unleashed angry dogs made for mandatory sprint intervals, even angrier rednecks in pickup trucks threw empty Sobe bottles while buzzing you with their side mirrors, and there was always a headwind no matter which way you rode. We used to joke that if training on the west side of town didn’t kill you, you’d win the Little 500. But the west side also had some of the most beautiful terrain for riding. There was nobody else out there except for the Cutters, who always secretly trained on the west side.

We pedaled back to Bloomington from Ellettsville and memories of the rowdy west side came rushing back. It was late in the day, the wind was in our face, the hills were relentless and the roads were beat up from one hard winter after another. Thankfully there were no angry dogs or rednecks, seemingly less common than they were 25 years ago. We hammered in a paceline along Vernal Pike and Ratliff Road, wondering why Bloomington felt so far away still. Our group became a bit weary–the west side and the old “B-town bonk” was taking its toll just like it used to.

As we sat at the lunch stop on Sunday feasting on more fried chicken, listening to live bluegrass and taking in the remarkable diversity of participants and the bikes they ride, Adam paused with a greasy drumstick in his hand, looking at a guy riding by on a 30-year-old Schwinn, completely oblivious to the fact his rear tire was flat.

“This ride, man. It hasn’t changed at all,” said Adam. “The Hilly is still the people’s ride.”

The people’s ride has welcomed every type of cyclist and every kind of bicycle since the 1960s. The Hilly attracts a range of nationalities and age groups, creating the widest definition of what a “cyclist” actually looks like. In the eyes of the Hilly, if you ride a bicycle, any bicycle, even if you push it uphill on foot and train only to eat fried chicken, you’re a cyclist. If there were more events like the Hilly Hundred, there’d be more cyclists in America.

Despite the Hilly’s endearing legacy, the event management seems to be as doggedly old school as the bicycles ridden in the event. In the 1990s, the Hilly brought upwards of 5,000 cyclists. Some years it was so busy that climbs like Bean Blossom Road were packed side to side with riders, many on foot in a scattered conga line. This past year the event hosted approximately 1,700 riders, not a bad number at all, but a fraction of what it used to be.

According to friends who ride the Hilly each year, the routes haven’t changed in a long time. Considering there are endless road options in every direction from Bloomington, mixing up routes each year might help future attendance.

It might also help to move the start and finish of the Hilly from Ellettsville back to Bloomington where it was for more than 30 years. Bloomington is where thousands of college-age student cyclists live, and could be a great way to attract a new generation of participants by offering a free Hilly entry to anyone with a valid student ID, marketing it as a scholarship, funded in part by adult registration.

By Sunday afternoon we had covered 107 miles with 5,400 feet of climbing, plus a bonus five miles and 300 feet of ascent up the Knapp’s painful wall of a driveway to finish. Between the peak fall colors and the perfect temperatures, we couldn’t have had better timing for our ride down memory lane.

Thankfully, Adam and I were not jaded by nostalgia. Bloomington is every bit as special as I remembered it, and this long overdue homecoming reminded me of how fortunate I was to attend Indiana University. Between the influence of the Hilly Hundred and the Little 500, Bloomington’s deep roots as a cycling community are the foundation of my identity as a cyclist. It still has some of the best roads for riding in the country, and for thousands of other cyclists across the country with Hoosier roots, I know they’d say the same about the magic that lies beneath the bucolic rolling limestone hills of southern Indiana.

The following story is an excerpt from CADENCE, a collection of road cycling tales from around the world. Each piece is told to inspire, to bring us closer to the characters and communities, near and far, that are all connected by the common bond of a life lived on two wheels.

Related Stories