English professor tallies 50th state on motorcycle, adventures galore

Robert Flynn heard his first motorcycle before he saw it.

In the backseat of his parents’ station wagon, Flynn craned his neck as a biker—dusty leather vest, long hair, and tattoos—rumbled up on a Harley, hands gripping ape hanger handlebars.

While Flynn’s parents exchanged glances, the 6-year-old saw “the coolest guy ever.”

Almost 50 years later, that boyhood fascination has stuck as the San Jacinto College English professor just toured his 50th state, Hawaii, on motorcycle.

Opening act

Growing up in Rochester, New York, Flynn itched to get his hands on a motorcycle, but his parents banned them at home.

Robert Flynn
Exploring on bike

In high school, he bought and stashed a dirt bike in a friend’s barn—only to have the game up when he came home mud-caked.

Majoring in theater in college, Flynn landed in a Disney co-op working at EPCOT and Magic Kingdom. He drove a double-decker bus, choreographed shows, and greeted guests as costumed characters like Tigger or Little John. Not only did it give him acting experience, but it also paid for his first road bike.

Bachelor’s degree completed and bike in tow, he moved to Los Angeles and “did the struggling actor thing” with commercials and lower-budget films for nine years.

Next came testing and designing video games and relocating to Boulder, Colorado. But when the game company shuttered its Boulder office, what was left but to return to Rochester and pursue a master’s in creative writing?

Tigger to teacher

From Disney character to college professor, Flynn calls his journey to reach the classroom a “rather circuitous route,” with motorcycles all along the way.

The Rocky Mountains first invited him to explore with overnight bike trips.

Scenic Overlook

Although Robert Flynn has many U.S. sights left to see, he counts these his favorites:

  • Alaska
  • Grand Teton National Park, Wyoming
  • Grand Staircase, Utah
  • Western Montana
  • Estes Park, Colorado

“Where can I go that I haven’t been?” he said. “That’s literally how it started.”

Back in New York, a short-term high school English teaching job helped Flynn finally connect the dots to a career in education. The only snag? He needed a warmer climate. Although he toured the northeast in his spare time, snow and freezes kept his bike garaged half the year.

“I was being very picky,” he said. “This was career No. 4 for me, and my primary hobby had been motorcycles since the ‘80s.”

In May 2012, San Jac called while Flynn was at a campsite on a motorcycle trip. By August, he had accepted an English professor position and moved to “milder” Houston. Almost 10 years later, teaching—like riding motorcycles—has stuck.

“If I had known how much I would enjoy teaching, I would have pursued it much earlier,” he said.

Backroad biscuits

Flynn has since ticked off the remaining continental states on motorcycle, including a summerlong, 20,000-mile round trip to Alaska. His Alaska bike, a BMW R1200GS, has almost logged 100,000 miles.

What are the essentials for long-distance trips? First, GPS tracking so Flynn can share his coordinates with first responders, if needed. Then a tent, food, spare gas, water, and a week’s supply of clothes stashed in the BMW’s storage compartment.

Oahu's North Shore
Oahu's North Shore

If he claims any road ritual, it’s sticking to backroads, ordering sausage and biscuits at a mom-and-pop diner, and chatting with locals at the counter. Each evening, he kicks back at a campsite and journals the day’s stories. And with 20 travel notebooks, he has plenty of memoir material.

“I tell my students, ‘Talk to people. Don’t just sit down with your earbuds,’” he said.

This past December, Flynn and his wife, fellow San Jac English professor Julie Groesch, crossed off Hawaii together.

On biking day, Flynn curved along the small roads of the North and East shores of Oahu on a rented BMW. Then he switchbacked through the mountains, catching panoramic, sun-washed views of Honolulu and Diamond Head.

The only hitch in an otherwise perfect day was a last-minute downpour. Clothes drenched, water still beading on his helmet, Flynn handed over the bike’s keys.

“At least my waterproof boots kept my feet dry,” he said. “For what it’s worth, riding in the rain in Hawaii is a tad more pleasant than riding in the snow in Alaska!”

Change of scenery

Since that first biker inspired him five decades ago, Flynn has maintained an adventurous spirit—from touring every state to joining the inaugural faculty of San Jac’s fifth campus, Generation Park, in 2020.

“It was absolutely an opportunity I couldn’t pass up,” he said of helping to open a new campus.

His checklist didn’t end with Hawaii either. Next, he’s eyeing the remaining Canadian provinces, South America’s Pan-American Highway, Route 66, and Highway 50 from Maryland to California.

What is an adventurer? For Flynn, it’s embracing rather than fearing change. Moving cross-country. Detouring off the highway.

“When a door opened, I went through it. When opportunities arose, I explored them," he said. "Not letting change scare me is the single reason why I’ve had moderate success in so many different areas.”

Banner image courtesy of Gijs Coolen, Unsplash.com / Story photos courtesy of Robert Flynn