#7: Road Trip with NO Destination

This is part of our 100 Things in 2014 challenge. Here’s the full list.

This is one Becky was dreading. Normally, she pours many hours of effort and thought into making sure our trips are successful – deciding where to go, arranging for lodging and food and comfort and entertainment, and making sure everything that can be known up front is.

But this was an exercise in restraint. Here are our rules (you knew we’d have some):

  1. The direction of travel will be decided at random, by pulling it out of a hat.
  2. Once the first draw is made, we travel two hours in that direction, to get out of our “zone of familiarity.” Subsequent draws are not subject to this rule; we were allowed to choose a reasonable place to draw again.
  3. No freeways allowed after the first leg.
  4. The first draw can’t be west. We know the coast pretty well, and the point is to go somewhere new.
  5. Stop at every historical marker, interpretive trail, general roadside point of interest, or place that Becky wants to stop.
  6. Paper maps only for planning. We use Urban Spoon and Yelp pretty extensively to find places to eat, and our car’s GPS so we don’t miss a turn, but ye olde atlas is the only tool for deciding on a destination.
  7. No eating at chain restaurants. Be as local as possible.
  8. No timetables allowed. When lunchtime arrives, we could start looking for food. We can’t plan our lodgings until we know the city/town/village/cave we’re going to stop in. (This caused problems, see below.)

SNEAK PEEK: I recorded our trip on Google Maps. Unfortunately I can’t embed it here, but you can click this link right here or this screenshot to see it:


Day 1

We dropped the kids with their grandparents, gathered everything we thought we’d need (including our passports — Canada isn’t that far away), and set out. The first draw: EAST. We thought Hermiston would be far enough out to satisfy the Unfamiliarity Principle, but we decided to stop in The Dalles at this adorable little Australian tea shop, which you should totally stop at if you’re ever in the area. Hermiston turned out to be super boring, and didn’t have a cool downtown that we could find. So we stopped at a park for the restrooms and to replace our water (Portland had a tap-water advisory that weekend), and to draw our next stone: SOUTH. We looked at the map, and decided that Heppner would be our next stop. Unfortunately all the restaurants were closed for the weekend, so we made a picnic from the grocery store, and “enjoyed” it in the rain at a little park, under the eave of the bathroom. Second. Saddest. Picnic. Ever. We scrambled back to our car, and drew again: EAST, to Ukiah. Our car’s GPS took us on a rather interesting road. In fact, Google won’t even route you on that road. If you click through to the map up above, I had to draw our actual route in by hand. It was nerve-wracking and slow (neither of us has ever really driven off-road), but our standard-Portland-issue Subaru was up to the task. It was pouring when we got to Ukiah, so we don’t have any photos. It was getting late, but there was nowhere to stay, so we continued eastward, choosing La Grande as our destination. But lo: an interpretive trail! The rules say we have to put on our rain gear and walk it. Upon reaching La Grande, we realized what weekend it was. Most of the motels only had suites left, so we ended up in a room at the Super 8 that had at least seven different kinds of chair.

Day 2

The next morning, we sought out the best breakfast we could find: The Dusty Spur, which is very Cowboy, and very good. On our way out of town, we noticed the farmer’s market! We bought strawberries and vanilla-fig balsamic vinegar. Our first draw of the day: EAST, to Union, which is as charming a town as you’ll find in Oregon. When people talk about small-town sensibilities, this is the place they’re referring to. Our next draw: SOUTH, towards Baker City, but as per the rules we avoided I-84. When you travel the smaller highways, you run the very serious risk of finding a historical marker…or getting trapped behind a cattle drive trying to reach a wildlife viewpoint. We followed this parade for 20 minutes before giving up and turning back towards our destination. Or maybe you’ll find Haines, a once-important railroad stop that now has a fascinating collection of 1800’s cabins and huts. We finally reached Baker City, and found a nice cafe with grass-fed beef for lunch. Afterward, we wandered around the downtown for a bit, poking around in antique shops. With the lesson of the night before, we decided to break one of our rules and plan our stop for the evening. We even skipped the randomization step – it was time to start heading back towards our neck of the woods. We spent a good 45 minutes calling every motel and Airbnb we could find that was in the right area, and we finally got one locked down and hit the road. But it’s never simple with us. We found an interpretive trail, and discovered where the term “switchback” comes from. We had quite a ways to go still, so there weren’t many stops this afternoon. But you can’t not stop at a ginormous covered wagon with a gorgeous valley in the background. It’s in the rules. We finally reached John Day, a visit we did not enjoy. Our lodgings were the worst room either of us had ever stayed in, no contest. We went for a giant walk until dark to avoid hanging out in it. The restaurant we went to for dinner was devoid of character, and served bland food. Maybe it’s just our bad luck, but this was the least-enchanting town of our trip.

Day 3

This was to be the last full day of our road trip. The time for randomness had passed; we had to be ready to pick the kids up and head home the following morning, so we chose WEST for our final direction, pre-arranged lodgings in Eugene, and started our day. Now, with most of our lodgings, we like to relax in the morning. Sleep in. Get a cup of coffee. Take a shower. Bring breakfast back. Hit the road around 10. Not here. We were out of there by 7 am. Nothing in town was open, so we just drove, hoping for something better a ways on. We found it, in the form of a lovely diner in Dayville, which despite also being named after John Day, was much nicer. Why, just look at all the heads mounted in this gas station! Seriously, though – this town was gorgeous and friendly. Right up there with Union. Not too much further on, we saw a sign for a geological marker! It only took us 10 minutes to find it on the far side of this unmarked rock. Then we reached the first of the gorgeous geological wonders of the day: the John Day Fossil Beds. There was also a shoe tree. For no apparent reason. We stretched our legs and wandered through some antique shops in Mitchell. And no visit to this part of the state is complete without a stop at the Painted Hills. This is where we started seeing the holiday-weekend crowds again, even though it was barely 10am. We plowed onward, passing through Prineville, and back onto familiar roads. We stopped just past Redmond at Cline Falls State Park for a picnic lunch and duck viewing. We also stopped in Sisters, which (believe it or not) has a community labyrinth. Then onward to Eugene. We found our lodgings, grabbed some dinner, then met up with some old friends and their twins for an evening of cuteness (and ice cream) downtown.

Day 4

That’s pretty much the end. After a long walk to breakfast, we jumped on I-5 and headed home. Not much scenery to show off.


This was quite an experience. Here are a few things we learned:

  1. It’s hard not to plan. We have to plan to not have a plan.
  2. There’s way more variability in Oregon towns than we had thought. We saw the best and (we hope) the worst.
  3. Despite the anxiety leading up to this, it was really relaxing. You spend the day just driving until you see something interesting. No timetables or deadlines, nowhere in particular to be.

We’re still going to plan most of our trips like we usually do, but we came away from this appreciating how our parents and their parents traveled. And this might make it on to our list for next year. And the next year. It’s hard to get across how much we loved this.

Total miles driven: 740. (Plus the off-road detour, which felt like 50, but was probably only about 5).

One thought on “#7: Road Trip with NO Destination

  1. Pingback: #74: Heathman Hotel High Tea | Band of Charac­ters

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