There are five things that make a trip memorable.

And I’m not referring to which hotel you stay at, even though I should be, because that’s my job and “area of expertise.”

I have also acquired quite some expertise in travel as a way of living. What you’ll find here skews in that direction. This list can be applied to any type of trip. It can also be applied to life.

Let’s ride.

Number 1: The Bump in the Road

📍Bend, Oregon

If your trip goes 100% smoothly, you’re not traveling.

The restaurant you were dying to go to for dinner is closed because a pipe burst. You forget your passport at the hotel and miss your flight. You get a horrible stomach virus from the roadside ceviche your friend told you not to eat.

The bump in the road is liable to happen at any point during your trip. For me, this time around, it happened on day two, in Bend. (I should have known it was going to be a great trip from the very beginning.)

Per my previous post, the bump was re-organizing the entire upcoming week after plans with my original travel companion went sideways.

Bumps, by nature, are not so pleasant. But it’s how you land on the other side of them that makes a memorable experience. For some people, a smooth landing comes naturally. For others, a smooth landing involves a learning curve. Things like a meditation practice or four years of traveling without a set plan can help when the inevitable, unexpected roadblocks occur.

Take it from me.

Number 2: The New Food

📍Yachats, Oregon

This is straightforward. Food is culture, and culture is food. While visiting a new place, if you don’t try at least one local dish, that’s a waste of a trip.

Upon leaving Bend, I drove west to the Pacific. My first night landed me in an extremely overpriced motel in a small town called Yachats. (Are you even allowed to call yourself a motel if the base room rate is $250?)

Still, what joy to lay eyes on the Pacific Ocean! And what joy, too, to eat beside it. After 4+ hours on the road, I was famished.

I opened Google Maps, searched “fresh seafood”, and opted for Luna Sea Fish House. One, because I wanted something casual. Two, because I had already seen a few other Luna Sea locations on my drive down the coast. Local chains are always a fun option, in my opinion.

While I was originally craving something along the line of fish and chips, my eyes were drawn to a word I had never seen before: slumgullion. A localized clam chowder with bay shrimp and cheddar cheese.

Here was my Bourdain moment. I could hear him in my head telling me to order the weird thing I’d never heard of. Ugh, I’m just not a chowder person, I replied to Tony’s ghost.

I am now.

This Oregonian concoction was the creamiest, richest, most flavorful mix of fresh seafood and cheese and spice to ever grace my mouth; I stopped every few bites because it was so rich—and also because I needed to text people about it. I will forever more be tempted to order chowders in hopes of finding one comparable. This is not likely, but that is precisely the point. I will always remember this soup, and thus, this place. Hello, gustatory memory.

Side note: I didn’t have a single bad meal in Oregon. I think it has something to do with how focused Oregonians are on hyper-local dining. For example, in Bend, I ate a breakfast sandwich from Farmer’s Deli where every component of it (bread, egg, cheese, bacon, etc.) was listed alongside the farm/bakery it came from. Would recommend.

Number 3: The New Transportation

📍Highway 101 & the Redwoods

Local bus blasting Reggaeton at 7 am. Crowded commuter train with no A/C. 10-seat seaplane. Tuk-tuk. Limousine. Donkey.

It doesn’t matter which form it takes—get from point A to point B via a mode of transportation unfamiliar to you. It may not be comfortable, but I promise you it will be memorable.

On this trip, my unfamiliar mode of transport took the form of a Toyota Prius: the smartest, most beautiful, and certainly most mileage-friendly passenger vehicle of my life. I’ll admit beauty was in the eye of the beholder—I hadn’t driven a car in over three years—but I also believe whipping around this part of the U.S. would bring a tear to any nature-lover’s eye.

Logistically speaking, you need a car to explore this part of the States. While bus lines connect major cities, that’s not the reason you’re here. You road trip the Pacific Northwest because every mountain road offers views of endless pine trees. You drive the 101 for panoramas of the Pacific and its rugged coast. You need the freedom to stop and go as you please.

And here’s how I pleased.

I put together a separate post with the full road trip itinerary. For anyone curious, see: My 1,000-Mile Oregon Road Trip: A Highway 101 & Redwoods Itinerary.

I was meant to spend my final night of the road trip in the college town of Eugene, but ended up back in Bend for the night due to a bad accident that closed the singular highway through the mountains.

There was bump number two.

Number 4: The New Friend

📍Portland

When I got back to Bend for the night, I texted Gina.

I met Gina on my first night in town—through the original Bend friend. We spoke a lot that evening in the park (recall: the one without the leather jacket). Not only is she super cool, but turns out she’s also the Sales Manager for the best hotel in town. New life friend and new work friend—win.

When my first bump in the road happened shortly thereafter, we arranged to meet for a tour of the hotel and dinner. Both were a joy, as was her company, as I tried to process the weirdness that went down the previous day.

She was actually the one who relayed the leather jacket anecdote. Thank goodness for her.

Gina is cool enough that aside from killing it as Sales Manager, she also hosts a stand-up comedy night in Portland, which I promised I would at least try to catch the first hour of before I had to head to the airport.

As fate would have it—or because it’s 2026–my flight was delayed 4 hours, to the point where I ended up cancelling and rebooking for the morning, since the comedy show was a blast, and hanging out with Gina and her friends post-show even more so.

Travel friends are tough, because they are too often transient. Oftentimes, you spend a spectacular day with someone and never see them again. Other times, you meet but briefly every few years and manage to remain friends for life.

Both are entirely the point.

People make the place.

Number 5: Tie it all together.

The final tip for a memorable trip is trickiest—because you have no control over it. It just happens.

What happens is, at one point, you realize that one thing, or maybe everything, that happened during your travels, was for a reason.

You may realize it immediately, in the moment.

You may realize three years later, when you run into the friend you made on the road completely by accident and they introduce you to their cousin, who you end up marrying, or whatever.

Serendipity.

On this road trip, my sense of it was screaming from the get-go, for reasons related to literally all of the reasons above.

If my travel “friend” from Bend didn’t suggest stopping in Yachats and Jedediah Smith, I wouldn’t have had the best chowder and best forest experience of my life. I would not have known to go to either of those places without the local insight.
If I didn’t travel to Bend (only to have my plans get bent), I wouldn’t have met or had the free time to spend with my new friend, which then closed my trip with a comedy show surprise—a Portland experience I wouldn’t have had otherwise.
If my plans hadn’t been cancelled, I wouldn’t have needed to rent my own car. Without my own car, I wouldn’t have experienced the joy and freedom of driving again, ultimately creating the solo Pacific Northwest road trip I’d always imagined.
And so on and so on.

Serendipity, I suppose, is also a matter of perspective. It takes a certain mindset to see it. Otherwise, it’s just coincidence.

But that’s no way to travel, or to live.

ONWARDS,

Maggie

5 Tips for a Memorable Trip: An Oregon Highway 101 Itinerary