As an avid cyclist–and a newly minted retiree–I couldn’t resist the challenge: could I ride my bicycle across the country to my 35th reunion in 35 days?

I had done two-week tours and one-day rides of 100, 200, and even 300 miles. I’d also finished the 750-mile Paris-Brest-Paris ride in 83 hours. But I’d be 57 by my reunion, and I’d need to ride 110 miles each day. I started to train in earnest on January 1 and logged more than 2,000 miles before setting out for MIT on April 18.

My first day out, barely 60 miles from home, I hit some debris and fell. Despite a banged-up knee and a sore hip, I kept going. In Los Angeles, I joined a tour group, America by Bicycle, which had mapped out a mostly rural route to Boston, booked motels, and set up food stops. Besides transporting my extra clothes, the group would provide mechanical support–and the moral support of the other 28 riders. Although I was not the oldest (he was 65), my bicycle was 20 years older than anyone else’s! At 6’5”, I’m too tall for standard bicycles, so I’d had my 67-centimeter steel-frame custom made in 1983. With two top tubes for extra rigidity, my frame channels more of my energy into moving the bike forward, as less is lost to flexing. But this performance comes at a price: my 25-pound bicycle was five pounds heavier than most of the others’, making it harder to climb hills. And at 190, I weighed 20 to 30 pounds more than most riders. I was usually tired at the end of the day but always able to ride again the next morning.

When you’re on the road for five weeks, you think about a lot of things. You ponder world events, reflect on what you see (land is a lot cheaper in the New Mexican desert than in Berkeley; most Americans look overweight), pursue mindless exercises like looking for patterns in mileage readings calculated to the hundredth of a mile on the bike computer. In Kansas, it was hard to think about anything but the weather; we traveled across the state on pace with a storm system that spawned daily thunderstorms and nightly tornadoes. We made only one detour to avoid flooding, but several towns we rode through had flooded the day before we arrived or would flood the day after. When it rained, we sought shelter in barns, storage sheds, mini-marts, and homes. Despite several tornado warnings, I never saw a funnel cloud. But that was pure luck; we were just 40 miles from Greensburg, KS, the night a tornado destroyed 90 percent of the town.

I learned why Dorothy longed to leave Kansas–and why she returned. Kansans went out of their way to help crazy strangers who shouldn’t have been riding in such conditions.

My fellow riders felt as if we were trapped in the movie Groundhog Day, doomed to relive the same day until we got it right. The problems I had to conquer before I escaped included four worn-out tires and 11 flats. When potholes destroyed my rear wheel, I kept riding on a spare and ordered a new one online with next-day delivery. In Missouri I broke a crank arm; 2.5 square centimeters of forged aluminum alloy snapped as I sprinted up a hill. I fell but was not badly hurt. Although I could have tried pedaling with only one leg, I opted to travel by van for two days until we got to a town with a bicycle shop. A replacement crank arrived from home the next day. I learned that both metal and muscle fatigue with age–and that modern technology has its advantages. Without cell phones and the Internet, I would have been stranded for a long time.

On May 24, we dipped our wheels into the Atlantic in Salisbury, MA; I had completed my nearly 4,000-mile trek on schedule. After a day’s rest, I was back on my bike for a ride to Lexington with the MIT cycling team. At the reunion, classmates asked if I was riding back to Berkeley (I flew) and if I would do it again. I might. Whether you’re crossing the country on a bicycle or attending MIT, the mind quickly forgets the painful parts of a journey, dwelling instead on the pleasure.