Like many people enduring the pandemic, I eventually grew weary of staring at the same four walls of my apartment and began delving once again into video games as a way to cope with the simultaneous stress and monotony of the last 14 months. Whether it was Animal Crossing, Stardew Valley, or even Civilization VI (a must for this history professor, with all its attendant issues), I’ve found immense comfort in relaxing into a digital world for a while. This is why the announcement of the release of a revamped edition of Oregon Trail immediately caught my attention — despite my misgivings as a historian of colonialism, settlement, and empire. This new version, released by Gameloft and available through Apple Arcade’s new suite of programs, promised a significant re-hauling of the game mechanics and a new focus on including Indigenous North American perspectives and characters. I was cautiously optimistic and logged in with excitement.

Playing the new Oregon Trail is a deeply nostalgic experience. For those of us late-Gen X/elder Millennial observers (I’m thirty-seven), the game is steeped in a particularly thick element of childhood nostalgia: sitting in computer labs or at bulky home desktops worrying about wagon axles, rations, or fording rivers. The changes are marked, while still balancing the appeal of what I remember from my childhood digital history lessons. You still have to worry about the health of your intrepid settlers (dysentery included!), gather food, cross endless terrain, and ideally reach your promised land. Yet, Indigenous North Americans are no longer background characters in what was, upon reflection, a wildly solipsistic game. In historically accurate clothing, fully playable and realized Indigenous characters respond to settlers as equals, have full dialogue, and even their own game play scenarios. I found this a powerful and significant reframing of a childhood game that worked considerably to become more inclusive, historically responsible, and cognizant of its history of dehumanizing Indigenous peoples. Gamesloft worked with historians Willy Bauer, Katie Phillips, and Margaret Huettl to recapture the spirit of the game as an engrossing, nostalgic adventure that also recognizes the humanity and centrality of Indigenous peoples. Yet, as I continued to play this past month, I felt a growing discomfort.

What does it mean to reform a game based on a violent history of land theft and appropriation? Including diverse perspectives and reframing the narrative away from plucky explorers and instead highlighting the peoples who were already there is a worthy and important goal. But at the same time, what does it mean to rehabilitate a game that nostalgically allowed people to play colonizing settlers in a country still too far from grappling with its violent, colonial history (and its present)? As Jezz Halfmoon poignantly observed as an Indigenous player of the original game, “I remember being like oh, like the Indians killed off somebody in your wagon train … and then being like, ‘Oh we’re Indians, you know.'”

As I continued to play the game, I thought further about the deep, historic anti-blackness and anti-indigeneity of the historic Oregon Territory our digital settlers were trying to reach. As I’ve written about previously, Oregon Territory not only explicitly banned Black settlement in the territory by referendum in 1858 (which was not overturned until 1927), interracial marriage was also outlawed (until 1951) explicitly in response to fears of Black and Native American corruption of the society these settlers hoped to build. What did it mean for Black children like me or Indigenous children like Halfmoon to play this game two decades ago? What does it mean to do it now?

For those who say that these reflections are a tall order for a simple video game to address, I can somewhat concede that it’s asking a lot. But for a game that was touted as an educational cornerstone for many of us, it fundamentally shaped how multiple generations first viewed not only Indigenous peoples, but the actions of settlement in the United States. It absolutely erases the violence that structured nearly every aspect of the Oregon Trail itself and the occupation of lands in the Pacific Northwest by settlers.

I am not saying that people playing the game are responsible for genocidal, settler violence, but as children we were somewhat unwittingly invited into the gamification of colonialism. As those Conestoga wagons rolled westward, our bankers flirting with dysentery and grueling paces, we placed ourselves in pixelated portraits of pioneers on flickering screens. We are nostalgic for those early computer memories, for the feelings of amusement and safety they elicited in us. But these games were also cosplaying conquest, rendering irreparable destruction as a pleasing form of play.

If, as the late anthropologist Patrick Wolfe claimed, “Settler colonialism destroys to replace,” then the Oregon Trail — both the historic process and the successful game series — are acts of writing colonial stories atop already existing peoples. What does it mean to reckon with this history? Can this legacy ever be reformed? These are questions I continue to ask myself as I think through what it means to head west on the Trail on my computer today.

T.J. Tallie is an assistant professor of African history at the University of San Diego, where he specializes in comparative settler colonial, Indigenous, and imperial history. He is the recent author...