Anatomy of a Mystery Trip

Way back in 2013, when Braden and I had only been dating for a few months, we decided to go on our first trip together. Even though I was working at a travel agency at the time, Braden took it upon himself to do all the research and planning. The catch? He wouldn’t tell me the destination until we got to the airport! All I had to go on was a series of clues about the city and what we would be doing there. Thus the Mystery Trip was begotten.

My friends and coworkers all thought it was the most romantic thing in the world, as they tried to help me unravel the clues. My mom and sister thought it might be a long con in which I might be kidnapped!

I heard this marriage advice from Bill Murray a few years ago:

“If you have someone that you think is The One, don’t do… don’t just sort of think in your ordinary mind, ‘Okay, let’s make a date. Let’s plan this and make a party and get married.’ Take that person and travel around the world. Buy a plane ticket for the two of you to travel all around the world, and go to places that are hard to go to and hard to get out of. And if when you come back to JFK, when you land in JFK, and you’re still in love with that person, get married at the airport.”

That first trip to Portland together got off to a bit of a rough start. A little while after the plane took off, it seemed like we were flying too low. And the city lights of Houston weren’t receding into the distance. Were we circling? An announcement was made: there was a problem with the door, and it wasn’t sealing properly. Basically if we went any higher, we would lose cabin pressure. So went back to Houston. Luckily, there was a replacement plane available right away, and we were soon Portland-bound again.

Then when we were driving away from the Portland airport in our rental car, we got pulled over because we’d forgotten to turn on the headlights. (The cop let us off with a warning.)

Houseboats on the Willamette River.

Despite the initial complications, it was kind of a perfect scenario to give our relationship a bit of a test. We could each see how the other would react to the setbacks; no one freaked out or got upset. I’m a worrier, and I think back on this whenever I start to fret about the things that might go wrong on our upcoming adventure: it will be fine; we will figure it out. And we’ve got each others’ backs.

The rest of that trip turned out perfectly, and we still talk about how everything fell into place. We climbed Multnomah Falls, saw a roller derby match in Hood River, and went to an all-you-can-play arcade. Our hotel was right across the street from a whole city block lined with food trucks. We went on a dinner cruise down the Willamette and strolled through Portland’s gorgeous International Rose Test Garden. We made sure to stop at Voodoo Donuts before heading to the airport on our last day.

We didn’t find any diamonds. 🙁

And every year since, we’ve done a Mystery Trip:

2014: Little Rock, Arkansas: Riverfest music festival, digging for diamonds at Crater of Diamonds State Park, and the Heifer International ranch. We ate at Your Mama’s Good Food twice; sadly it is now closed. 

2015: Milwaukee, Wisconsin: Yoga at the Milwaukee Art Museum, cheese curds, a Brewer’s game, coffee at the Public Market, and breakfast at County Clare Irish Restaurant with Paralympian Tom Miazga!

2016: Boise & Stanley, Idaho: Swimming in the hot springs, paddleboarding at Redfish Lake, listening to the Hamilton soundtrack, off-path hiking, shopping at the farmers’ markets, and watching the Twilight Criterium bike races and a Boise Hawks game.

Floats at Fitz’s

2017: St. Louis & Southern Illinois: Tons of amazing hiking, almost getting sucked up by a tornado, getting engaged at Burden Falls (it’s the tallest waterfall in Southern Illinois!), a whole fried chicken for $6, lunch at the Opera House Bistro, going up the Arch, Ribfest in Ferguson, and insane ice cream floats at Fitz’s

2018: New York City: Come From Away, Blank the Musical, Puffs the Play, the Math Museum, the Highline, Museum of the City of New York, food festival in Hell’s Kitchen, a poetry reading in Greenwich Village, jazz music on a rare Hammond B-3 Organ in the American Legion hall in Harlem, riding the subway, walking 30,000 steps in one day, bagels and donuts for days, and meeting up with friends. 

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