If you grew up during the ’90s, chances are you played Oregon Trail, the educational video game where you did little more than press buttons and ration your spendings (and meals) until you either made the 2,200-mile trek … or died of dysentery. And it seemed like everyone died of dysentery. So much so that it became a t-shirt years later.

Yes, it was meant to teach kids about the history of early pioneers moving across the country in search of a better life — and the incredible hardships they faced — but in the ’90s, those 8-bit graphics meant one thing to kids everywhere: Score! We were playing a game in school! (Or, in my case, after school, since my friend Bethany’s mom basically let us have our pick of doing that, watching poorly dubbed live-action Pippi Longstocking episodes, or jumping on the trampoline in the backyard. When it was raining, we hit the Trail, Windows 95-style.)

So, when Buick sent out a handful of invitations to check out its modern “wagon” (AKA the Regal TourX) and compete on a modern-day, live-action version of the game, I jumped at the chance. I went with a colleague, and we were one of seven teams to fight to the finish line, all in the name of a great story to laugh about later.

Each day brought its set of challenges, but here are the highlights:

Day 1: Supermarket Sweep, 1890s Edition

Remember how Miss Congeniality taught you that the pageant wave meant going elbow, elbow, wrist, wrist? A similar motion’s required (largely in the wrist) to properly lasso a cow. Or a hay bale dressed as a cow, I soon learned.

As we made our way through Wyoming, we stopped for provisions. Like the game, you had a finite amount to spend, but we went buckwild, scooping up everything from canned vegetables and toilet paper to a kayak (when are you not asked to ford a river during that game?!) and crutches (c’mon, everybody gets delayed due to a broken leg; it’s inevitable).

Day 2: Glamping Gone Wild

Sure, there was a paintball shootout (billed as “hunting”) and a biscuit-baking contest (which we tied for first!), but the real thrill, to me, was Conestoga Ranch’s killer glamping setup. The Utah campground boasted the best food I ate that week — steakhouses and top-billed Portland restaurants included — as well as a mini arcade and a live band.

Every tent had its own queen bed, fireplace, and stock tank bathtub (no outhouses or peeing behind trees here!). When you checked in, you were given a set of s’mores ingredients, so you could heat up your own dessert over the giant campfire outside of the ranch’s grill. It may have been 40 degrees that night, dipping to a frigid-at-best 28 early that morning, but it was the highlight of the trip.

Day 3: Deadly Diseases Pop Quiz

Each day involved 6-8 hours’ worth of driving, which made for a great selling point for the car, considering it was equipped with wifi, heated seats and had a smart cruise control that slowed down as it noticed traffic up ahead. We made our way to Boise, Idaho, where we were grilled on our CPR skills (spoiler: mine need work if I’m ever saving anyone’s lives), raced to splint a leg the fastest, and quizzed on the diseases most likely to kill someone traveling the trail in the late 1800s.

As much as I joked about the diseases I didn’t actually understand as a kid, learning about their true effects was horrifying. Diptheria? Oh, it’s an airborne disease that slowly suffocates you. Dysentery? Imagine an extreme version of diarrhea that can kill you. I’ll spare you the rest.

Day 4: The Final Ford

It was 49 degrees outside and rainy, but that didn’t squelch my competitors’ spirits. Everyone dove into the kayaking challenge, fighting against the current in Portland, Oregon, to make it to our final stop: The very end of the Trail. We were greeted with champagne and cheese platters, capping off the cushiest way to travel a (truncated) version of the trail.

As lighthearted as it was, it gave me a whole new respect for what people endured to start a new life. Of the roughly 300,000 people who traveled the trail, an estimated 65,000 died along the way. Faced with that journey — and the decision to even embark on it in the first place — is enough to melt my everyday gripes and concerns away. Long commute? That’s nothing. Flu got me down? No biggie. Perspective is a powerful thing.