Diaries from the Oregon Trail: Life Is a Long, Hard Caulk

Originally Posted October 12, 2011


9/26/11 7:10am

As we come to the Mighty Mississipi, we are faced with our first major decision. To ford, caulk, or take the ferry across these rolling waves of certain death. You can’t help but wonder how any of our ancestral brothers made the trek to Portland for advertising jobs. Alas, I digress. Our problems began way before we reached this most thunderous torrent in the Midwest.

As the early pioneers once did, I prepared for my long journey by getting an oil change and filling the gas tank of my Ford Explorer (from here on out to be referred to as “the wagon”). My father, R. James, and I, T. Jonathan, loaded our wagon with supplies in an attempt to become the first ever Siolka’s to settle the west coast. Before I even had a chance to kiss my poor Ma g’bye, we hit a serious snag.

The wagon didn’t have an iPod dock! Seriously, I had to use a tape deck adapter. That doesn’t even charge your iPod! Lord only knows how the early prospectors did it without this underappreciated device. However difficult the road ahead looked, we pushed forward.

Now where was I, ah yes – The Mississipi. As I stare death in the face, knowing that the wrong decision will make a lonely widow of my mother, I consider my unfavorable options. Do I take the ferry or cau—shit, we already went over the bridge. I guess we’ll caulk the next one.

9/26/11 11:43am

Things are really getting tough now. We’ve hit a pocket of poor cell phone reception that has been going on for miles. And when I can squeak a bar out, it’s not even 3G. Maybe doing some hunting will take our mind off of it.

We stopped at a convenience store to hunt for buffalo. Although we’ve shot 18,000 pounds of bison, we’ll only have enough room to bring a bag of taco-flavored Doritos. Father’s looking thin. I hope the 4 hours of starvation isn’t getting to him.

This drive is really starting to get boring. South Dakota? More like South Da-really-fucking-boring-kota. The only thing that keeps us going is the promise of reaching Wall Drug soon. Praise the brave men who put these billboards up in the 1850s.

9/26/11 2:14pm

Fuck, we missed Wall Drug. All that hype and we flew right past it. The disappointment is overwhelming. I guess we’ll have to stop at Dairy Queen to lift our spirits.

The hardships continue. It took nearly 5 whole minutes to get my chocolate shake. Watching the mammoth animals run this sad restaurant reminds me that there are things worse than death. We CANNOT get stranded in South Dakota.

Finally, we approach an oasis of life. Deadwood, SD – straight ahead. A town known for its raucous boozing, competitive gambling, and women looser than a noose on a noodle.

9/27/11 1:28am

Apparently everyone living in Deadwood was an original settler of the small town. I’ve never seen more rolling walkers. I’m looking to throw dice off of a hooker’s naked ass and I find busloads of senior citizens playing the penny slots with their dentures sitting out in lowball glasses. But like the traveler’s before us, we made the best of our situation. After all, less partying for the grandmas means more for me and pop pop. Deadwood, consider yourself owned.

9/27/11 10:22am

Entering Wyoming – cowboy country. Scenery is beautiful but I only have one question. How could any cowboy be gay when every hill looks like a boob? Brokeback- lies, all lies.

9/27/11 2:40pm

We’ve been in Montana for some time now. No sign of Hannah yet. We’ve stopped to pay homage to the site where Custer had his last stand. There are signs at Little Big Horn that worn us of possible rattlesnakes and to not use our cell phones. How terrifying to be one of Custer’s men, knowing that even if you came face to face with a violent American Indian, you couldn’t use your smartphone to take and tag a Facebook pic. Brave, brave men.

9/27/11 6:01pm

Still no sign of Hannah. Father is starting to complain of the dead skunk stench Montana has to offer. I don’t have the heart to tell him that what he smells is my flatulence. There’s no time to be worried over the presence of dysentery. We must make it to the coast.

9/28/11 1:12am

Almost home. We’ve stopped for one final night. Although dysentery nips at my buttocks and I could really use penicillin, we decide to spend our remaining money on whiskey and keno.

Observation: the people of Montana are nice. Willing to help at any cost. Unlike those of South Dakota, who acted like they were just waiting to die.

As stated, we gambled our money away. The bookkeeper was a strange but kind man. The kind of man whose first name is “Uncle.” I hope he’ll use the money he earned from us to pay for dentistry. His kindness deserves a full mouth of teeth.

9/29/11 10:28am

Welcome to Oregon! We’ve defied all the odds and made it to the Promised Land. They say anything is possible here. Anything… anything…well apparently anything but finding some gall damn satellite TV! How in the hell am I supposed to watch the Brewers out here?! Was this not the first thing Wisconsin settlers did when they reached the coast?! NO ONE WARNED ME THAT THE PRIZE AT THE END OF THE OREGON TRAIL DID NOT INCLUDE SATELLITE TV!!!!!!!