The Legend of The Oregon Trail

filed under: computers
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Illustrations by QuickHoney

by Jed Lipinski

Three student teachers changed the educational game industry from inside a janitor's closet.

In the fall of 1971, Bill Heinemann and Paul Dillenberger returned to their Crystal, Minn., apartment to find their roommate, Don Rawitsch, sprawled on the living room floor, drawing a map of western America. The three men, all seniors at Carleton College, were student teachers. They spent their days in junior high classrooms teaching math and history in inner-city Minneapolis. At night, they huddled over dinner, sharing tips and debating teaching techniques. Until earlier that day, Rawitsch had been stumped on how to get his eighth-graders interested in his new history unit, “The Western Expansion of the Mid-19th Century.”

It wasn’t for lack of trying. Rawitsch had attempted everything from peppering his lectures with strange and compelling facts to showing up to class in full Meriwether Lewis regalia. Nothing seemed to work. But now, as he furiously sketched his map on long sheets of butcher paper, he thought he was onto something. “I’m making a board game about the Oregon Trail!” he announced to his roommates. Rawitsch pictured a game in which students would become pioneer families traveling the treacherous 2,000-mile route from Independence, Mo., to the Willamette Valley in Oregon. They would set out in ox-drawn wagons and purchase food, clothing, and ammunition; along the way, they’d encounter a series of historically accurate calamities. Surely, nearly dying from snakebite or exhaustion would get the kids’ attention, right?

Rawitsch planned to add an element to advance players across the board—perhaps dice or instructional cards. But his roommates, who had taken a few programming classes, had a different idea. “What if we put this thing on a computer?” Heinemann wondered. Instead of the pure luck of dice, the simulation could take into account the weight of your load or what you’d paid for oxen. Survival could hinge on your skill at shooting buffalo.

Rawitsch loved it. The problem was, he needed the game in less than two weeks.

Heinemann and Dillenberger glanced at each other.

“We can do that,” Heinemann said.

They had no clue that the game they were about to create would eventually sell more than 65 million copies and influence hundreds of millions of students. Not only wouldThe Oregon Trail go on to become one of the nation’s most popular computer games, it would become a beacon in the emerging educational game industry. But before any of that could happen, the trio needed to find a computer.

In the early 1970s, PCs were extremely rare. In their place, tech-savvy schools used teletypes: electromechanical typewriters that connected through a phone line to a mainframe computer the size of a room. So for two weeks, the roommates holed up in a former janitor’s closet at Bryant Junior High School, where the school’s teletype was stored, and spent their evenings programming. Using Rawitsch’s historical knowledge, Heinemann and Dillenberger developed a series of algorithms, punching hundreds of lines of code into the teletype. But just because they created the program didn’t mean they could breeze through it. When Heinemann tried The Oregon Trail for the first time, he died of pneumonia midway!

Rawitsch debuted The Oregon Trail in his classroom on December 3, 1971. He rolled the teletype into the center of the room, and the students gathered around. The machine churned out a roll of paper with questions like “How much would you like to spend on clothing?” When a kid typed in a number, the machine delivered a new question, along with an update on his or her condition. Some imagination was required. In order to hunt, students had to type the word bang. If they typed the word quickly and accurately, the machine responded: “Good eatin’ tonight!” If they faltered, the machine sniffed: “A little slow on your Colt .45.”

It was no Grand Theft Auto. But for students who’d experienced computers only as glorified calculators, The Oregon Trail opened up a whole new world. After a few rounds, the kids who previously had no interest in history knew a little more about the geography of the Western U.S. and the brutal realities facing 19th-century pioneers. The game worked on a conceptual level too. “The Oregon Trail was one of the first educational software applications that put you into the program,” Rawitsch says. “Despite the lack of graphics, students who played weren’t students anymore. They were settlers crossing a wasteland. Their decisions were a question of life or death.”

What Rawitsch hadn’t expected was how the game would foster teamwork. Initially, when the machine asked questions, students would shout various responses. When this proved inefficient, they started putting decisions to a vote. “They invented democracy out of necessity,” he says. Students also realized the quantity of food available hinged on how quickly they typed bang, and they began taking turns and learned to delegate: The best typist got behind the gun; the budding accountant kept track of the expenses. “They were like workers in a Henry Ford plant,” Rawitsch recalls with pride. “Everybody had a job!”

With the game’s success established, the three roommates loaded it onto the school’s “time-sharing” system, which enabled other Minneapolis schools with teletypes to play. Soon Dillenberger and Heinemann were sharing The Oregon Trail with their own students, who lined up outside the janitor’s closet after class to take turns. It wasn’t long before the kids found ways to exploit the program’s bugs. Spending a negative amount of money on supplies, for example, increased your cash flow. “Kids are clever,” Dillenberger says, adding that he and Heinemann continually revised the source code to refine the program. Seeing how engaged the kids were was immensely gratifying for the three teachers. “It was reinforcing to know that we’d spent our time and energies well,” Heinemann says.

When the semester ended, the unit was over. Rawitsch had no more use for The Oregon Trail, so he deleted it from the time-share program. As a souvenir of sorts, he printed out the giant roll of code and stowed it in his apartment. It would be years before anyone braved the trail again.

At the time, the federal government was nervous about competition from the Soviets. To keep America’s kids ahead, the government handed out massive grants for innovative approaches to teaching. And educators in Minneapolis-St. Paul were ideally positioned to receive them; computer companies such as IBM, UNIVAC, Control Data Corporation, and Honeywell all had offices in the area, making it a kind of Midwestern Silicon Valley.

In 1973, a man named Dale LaFrenz unwittingly entered the history of The Oregon Trail. A former math teacher, LaFrenz was hired as assistant director of a new statewide body called the Minnesota Educational Computing Consortium. MECC, as it was known, was tasked with providing computers and computer training to schools and colleges throughout the state. At the time, Rawitsch was inquiring about a job. LaFrenz installed Rawitsch as an entry-level liaison for local community colleges and explained that MECC was building a library of educational software to be used by Minnesota schools. LaFrenz let Rawitsch know that he was open to his ideas.

Over Thanksgiving weekend in 1974, Rawitsch exhumed his old yellow roll of code. Looking at the game again, he knew he could do better. Over the next year, he would thicken the plot, using facts he found from the diaries of Oregon Trail survivors. He discovered how often settlers ran out of water. He tallied the ways people died, and he took note of how Native Americans, contrary to popular belief, were actually quite generous with survival tips, letting settlers know whether it was safe to cross a river, for example. With his old friends’ consent, Rawitsch factored these details into a new version of the game and spent a holiday weekend punching the code back into a teletype—this time one connected to 1,500 terminals across the state. Suddenly, thousands of students were accessing The Oregon Trail every month. With the exception of a primitive version of email, which allowed students to pass messages from one teletype to another, The Oregon Trail had become the most popular software program in Minnesota.


By the late seventies, RadioShack, Commodore, and Atari were debuting sleek new personal computers. Of all the brands, MECC chose to support the Apple II—a durable little PC produced by two scrappy unknowns named Steve Jobs and Steve Wozniak. In 1978, MECC delivered 500 Apple II computers to Minnesota public schools, marking one of the burgeoning computer giant’s first big sales.

Conveniently for The Oregon Trail, Apple’s software came packaged on diskettes, allowing the game to be easily shared and uploaded onto new school computers. Other state school systems, envious of Minnesota’s technical progressiveness, began purchasing binders of software from MECC. Suddenly, The Oregon Trail was in nearly 5,000 school districts nationwide.

With Rawitsch acting as a consultant, MECC’s young programmers, many of whom had played The Oregon Trail as kids, redesigned the game with basic four-color graphics. Now it was their turn to help shape the next generation’s view of computers. One twenty-something programmer tweaked the calamities, adding the grim announcement “You have died of dysentery.” (Today, it’s a popular T-shirt.) In subsequent versions, MECC staffers were recruited to sing popular folk tunes of the 1840s, like “Vive La Compagnie,” whose melodies were recorded and translated into beeps and buzzes to provide a soundtrack for the journey. Later, to aid in character renderings, MECC’s up-for-anything employees dressed in period costume (coonskin caps, hoop skirts) while an in-house videographer filmed them in front of a green screen. The game had come a long way from the text-only teletype version, which simply rang a congratulatory bell when players reached the promised land.

Through the ’80s and early ’90s, MECC dominated the so-called edutainment market. Its roster of games included hits like Word Munchers, Games With Words, and Spellevator—all programs that taught kids basic spelling or grammar through simulated adventures, like evading pixelated monsters or malevolent vacuum cleaners. But the bizarre storylines were only part of MECC’s formula for success. The real reason MECC games had become such a hot item in classrooms was their ability to give students immediate feedback. Instead of waiting for a teacher to grade papers or check a student’s work, the roaming Troggle that ate you in Word Munchers instantly confirmed your mistake. The Oregon Trail, which pioneered this technique, remained the company’s bestselling game. Its sales were so strong that in 1991 the State of Minnesota sold the company to a venture capital fund for $5.25 million. When MECC went public three years later, The Oregon Trail represented a third of its $30 million–plus annual revenue.

To celebrate the game’s enduring success, MECC threw a jamboree at the Mall of America in Bloomington, Minn., in February 1995. In the company of a live buffalo named Cody, Dillenberger, Heinemann, and Rawitsch—who’d left MECC five years earlier—were presented with matching jean jackets emblazoned with a logo that read trailheads. The former roommates signed a map of the real Oregon Trail and received the latest version of the game, The Oregon Trail II, which featured more roles for women and minorities, plus a dozen new ways to die (“accidental gunshot” and “gangrene” among them).

MECC’s future seemed rosy. Edutainment had become a $500 million industry, and profit-hungry corporations started circling around makers of educational software. Not long after the jamboree, publisher and distributor SoftKey International Inc. acquired MECC for $370 million in stock options. A month later, SoftKey snapped up the Learning Company, and in 1998, Brøderbund—the original creator of Carmen Sandiego—as well. But the results weren’t pretty. “SoftKey basically gutted the research and development side and put all its money into marketing,” said Scot Osterweil, a former designer for Brøderbund.

SoftKey, which renamed itself the Learning Company after the acquisition, axed popular games like Reader Rabbit and Madeline for not returning Oregon Trail-level profits. The company cut dozens of jobs from MECC's Minneapolis headquarters, forcing it to shut down in 1999. Later that year, toy manufacturer Mattel, which dreamed of letting Barbie rough it in The Oregon Trail, bought the Learning Company for more than $3.5 billion. Shorn of its talented staff, however, the Learning Company began hemorrhaging money. In 2000, Mattel posted a net loss of $430 million.

Despite all this, The Oregon Trail has endured. The iPhone version, released in 2009, has been downloaded more than three million times. The game’s Facebook page is thriving. Well-meaning parodies—like Fall Out Boy Trail, in which the band tours the country in an ox-towed van, and Organ Trail, in which players dodge zombies in a postapocalyptic landscape—abound. As Jon-Paul C. Dyson, director of the International Center for the History of Electronic Games, puts it, “The Oregon Trail taught generations of students not only about the history of westward migrations but also how to use computers.” He adds, “Any game that can survive so long in so many different variations has to be important.”

Today, the game’s three creators are still friendly. Heinemann teaches after-school and summer enrichment programs in math and chess. Dillenberger recently retired after nearly 40 years in Minneapolis public schools. As for Rawitsch, he lives in the Chicago area and works as a consultant to educational tech companies. And he’s still surprised by how much those two weeks of coding—three friends huddled in a janitor’s closet, programming at night—influenced his life. “The game has become part of our history for far longer than any of us could have expected,” Rawitsch says, laughing. “Being introduced as a co-inventor of The Oregon Trail has been a great icebreaker over the years.”

For all the game’s success, the roommates never made much money off The Oregon Trail. But they’re OK with that. “It’s become kind of a joke among us,” Rawitsch says now. “So many others had a hand making it what it became that we never think, ‘Gee, we got ripped off!’”

“We’re in awe of the effect The Oregon Trail has had on so many people’s lives,” Dillenberger adds. “How could we have any regrets?”

This story originally appeared in mental_floss magazine. You can get a free issue here or check out our iPad edition.

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July 29, 2013 - 1:20pm