In the summer of 1990, my sister and I died. A lot.

Some evenings we drowned. Others we succumbed to measles or exhaustion. We froze to death. We died of starvation. We were bitten by snakes. We contracted cholera and typhoid. A few times, we broke a leg or an arm. Back then, that was a death sentence.

Most often we died of dysentery.

We watched as our names were scrawled onto tombstones that would soon be lost to time. We thought it hilarious that the monuments read “Here Lies Butt,” laughing all the while and ready to start over just to—in all probability—die again.  

Alexis and I are part of what has been called the Oregon Trail Generation. That is, the little sliver of a microgeneration between Generation X and the millennials that some researchers bookend by the years 1977 and 1983. As I define it, we were the last generation to grow up without constant access to technology, the last to treat tech as an add-on to everyday life rather than a function of it. To wit: I didn’t own a cell phone until I left for college. I didn’t have my own computer until my junior year of college, instead relying on computer labs for writing papers. I didn’t realize until I was weeks from graduation that I even had a university-assigned email address, full of unread messages from the previous four-and-then-some years.

The Oregon Trail Generation was named for a computer game designed to teach kids history.

The game was first developed in the early 1970s by a trio of young Midwestern history teachers named Don Rawitsch, Bill Heinemann, and Paul Dillenberger. It was produced by the Minnesota Educational Computing Consortium and first published in 1975. By the late ’80s, Oregon Trail was ubiquitous in school computer labs around the country. Like most other kids in that decade, my sister and I grew up playing it as we waited for the late bus or got the coveted “play on the computer” directive from our teachers.

Early in that summer of 1990, my mother came home and asked Lex and me to unload something from the back of her minivan. Our mom made her living—and in many ways, her life—teaching special education in New Jersey’s public school system. Earlier that year, our school had purchased a brand-new Apple II computer. It was slate gray and the vanguard of technology.

For some reason, the school’s administration had offered my mother a chance to take the Apple II home for the summer. A lifelong writer, she thought she might use its powerful word processing program to work on her stories, which she had traditionally written longhand. And she wrote on it often. But at the end of most of those long, hot, summer days on the Jersey Shore, when my mother made her way to the kitchen, my sister and I would click on the Apple; transport ourselves to 1948 Independence, Missouri; load our wagon with supplies; and begin the treacherous journey that almost always resulted in death.

Lex and I spent untold hours that summer staring into the green-black screen of an Apple II, venturing from Independence to the Pacific Northwest along the Oregon Trail. It would be years before we learned about Manifest Destiny, about Sooners and the Great Plains and Little Bighorn, about stolen lands and genocide and blankets laced with smallpox. Back then, the long journey westward was just a means of occupying our time after the sun went down. It was a new adventure to augment sleepless nights we had spent trying to rescue the Princess from Bowser’s castle.

I especially loved to hunt; Lex was great at crossing rivers and puzzling out how best to load our wagons before trips even began. We passed plates of snacks back and forth: the era-appropriate (Dunkaroos, chocolate Twizzlers, and Fruit Roll-Ups) mingling with flavors of an Italian-American home (salami, tiny slivers of mozzarella, and, of course, Stella d’Oro cookies). Often, our own little resupply train would arrive bearing a smile and a tray of root beer floats.

During that summer, on two hard oak chairs borrowed from our parents’ dining room, I was closer to my sister than I had ever been before—or perhaps since.

Two years later, the MECC published a deluxe edition of the game, introducing all-new mouse control features. By then, our interests had begun to diverge. Lex was on the precipice of high school, where she would gravitate toward cheerleading and gymnastics. A few years younger, I began a lifelong love affair with music and the movies, aided in large part by the indie booms of the early ’90s.

Growing up, we were always close. But beyond being the children of our parents, my sister and I soon had little in common. Geography played its part. She went to a leafy university outside of Philadelphia. By the time I got to the same city for college, she had moved on to medical school in New York.

Eventually, following work, Alexis moved out to eastern Long Island, not too far from the very end of the world. Eventually, following my dreams, I moved to New York City, where I found a life and work in the independent record industry. We’d see each other from time to time. But we were both busy creating the lives we wanted for ourselves. She married her college sweetheart, and they soon became parents.  

After my mother dealt with the first of the few bouts of cancer that eventually killed her, my parents moved from the Jersey Shore to eastern Long Island, finding a home just a few blocks from Alexis and her growing family. They wanted to be closer to their kids in what they knew were my mother’s final years. I, just a few short hours away by the Long Island Rail Road, trekked east every few weeks for some much-needed respite from city life and to spend time with my dying mother.  

A few years ago, my wife and I left New York City, daunted by the costs of raising a family in Manhattan. We relocated to Chapel Hill, North Carolina, where it’s quiet and green and only 55 minutes by plane to the City. After a few visits, Alexis and her husband decided to follow our lead and relocated their family to the other side of town.

By the time Emily and I welcomed our first child, my sister had already had her third and final kid. Within our son’s first two years, he became obsessed with their youngest, a daughter. 

We live just 15 minutes apart now, closer than we have been since Lex’s bedroom was just down the hall from mine, before she left for college in the fall of 1997. And our kids spend a lot of time together.

They play as kids do, jumping on the big round trampoline at my sister’s or playing pop-a-shot in our garage. But after their energy has been spent they find their way to the couch, often under a shared blanket, beside a plate of era-appropriate and Italian-American snacks. Sometimes there’s a movie to watch, but mostly the two of them hover over my niece’s iPad, playing this game or that, and I can’t help but think of my big sister and me, looking out for each other on the dangerous trail, hunting and trading and fording rivers, sharing a bond that would never be replicated or matched, one forged over mountains and streams and nights spent in front of the green-black screen of a game that was, back then, the vanguard of technology.