20180515_183419  IMG-20180515-WA0101

Or: The Story of How I Overcame My Anxiety/Mild Phobia of Highway Driving with DIY Exposure Therapy (i.e. just driving, no escape) by Splitting an 11 Day Road Trip with My Ever-Patient Girlfriend! JK, I’ll save that riveting story for another time! But suffice it to say, when we planned this trip, I wasn’t ONLY thinking about all the food we were going to eat in Portland and the dramatic coastal landscapes we were going to see, I was also thinking about passing trucks at high speeds on the I-5 while remembering to focus on the MILES, not kilometres, on my speedometer, and lots of other things to do with driving. Obviously, I didn’t die, and I didn’t FEEL like I was going to die for at least MOST of the trip. Plus, it was so nice to have the flexibility to choose where we wanted to go and how long we wanted to stop. In conclusion: successful DIY project, and also: successful road trip.

K so back to Oregon: Here’s a guide to an excellent (IMHO perfect) Oregon road trip, based on a compressed version of our trip (we started in Vancouver*, spent an extra night in Portland, and had to stay the night in Port Angeles on the way home to catch the ferry to Victoria). Next up is the coast!


Part One: Portland

Check out my post from my last trip for more weird and wonderful things to do in Portland!

Day 1: Settling In

Good old Portland. As you get in, chill in the park. We arrived in the early evening in a heat wave, and within 5 minutes ended up at Laurelhurst Park watching a silent disco, surrounded by slacklines, hammocks, bicycles, Lamzak chairs, and basically every other Portland thing you can think of(/an extreme version of what we normally do on a weekend).


Once you feel hungry, head over to nearby Nong’s Khao Man Gai for classic chicken and rice with the most incredible sauce.

20180513_194012  IMG-20180514-WA0047

If you’re us, promptly go to bed and crash. If you’re cooler than us, consider grabbing a drink!  There’s really no shortage of places to choose from; on our last trip we enjoyed Mad Hanna and Beech Street Parlor, which are both in the area.

Day 2: Downtown Day

Grab breakfast at the Daily Feast, a hip diner where even visiting the bathroom is an adventure (like… to find, not because of what happens there). Breakfast chilaquiles, anyone?! Or good old bacon and eggs? Check, check.

20180514_121836  20180514_124601

On a nice day, take a stroll to the Tom McCall Waterfront Park, where you can check out the city’s bridges and watch a pretty neat lift bridge in action, if you’re as geeky as I am!

tom mccall waterfront park portlandDon’t forget your hammock, if you’re as hammock obsessed as we are! We spent the morning cocooning. Plus, the world’s smallest park is right across the street (in the street, if we’re getting technical).

20180514_130730  IMG-20180514-WA0083

Once you’re ready to move after all that brunch and feeling like a beer or 4, head back into downtown via the “Portland, Oregon” sign for a photo op.

portland oregon old town sign

Make a stop at Old Town Pizza in Chinatown, which is also a brewery, and apparently a haunted one at that! We were too full to try any pizza, but we loved their summery beers!

20180515_162631  20180515_162835

Next stop: Voodoo Doughnuts! The funky shop (cash only) and unique flavours and shapes make this Portland landmark an essential stop, whether you’re a doughnut lover or not!

Brewery number 2: hit up Deschutes, Back Pedal Brewing, Bridgeport (Portland’s oldest) or any of the others within a few blocks from each other.

IMG-20180514-WA0087  20180514_162134

If you’re a book person, or just a human person, prepare to set aside multiple hours to check out Powell’s City of Books, which takes up a city BLOCK and is the world’s largest new and used bookstore. There are loads of specific categories (we got lost in the LGBTQ+ section for a while), a rare books room, and great staff suggestions.

Hungry yet? There’s a block of food trucks right around the corner – Korean, Middle Eastern, Greek, Thai, the world is your food truck. The food trucks are you oyster? (Disclaimer: there are no oysters.)

After refuelling, if you’re feeling like a bit of old school fun with an adult twist, Ground Kontrol is the place to go. Old school arcade games & booze, what more could you want? I’m not a huge arcade game person but I always have fun there.

20180514_204007  20180514_205318

You could also head back to the breweries or hit up a bar but honestly Powell’s is open till 11 soo… But if you do want a drink and you want to be fancy, try Departure Lounge’s rooftop bar! It’s $$$ but if you time it right, you can get only $$-priced food and drinks at happy hour! (So maybe… go before dinner – A+++ itinerary!)

20180515_174331 20180515_17444420180515_182302

Day 3: Nature and Nurture

If you have a car (which you do, because this is a road trip) start with brunch at Gigi’s Café, where you can eat heavenly GF or Belgian Liege waffles topped with heavenlier fried chicken topped with maple syrup eh. I mean, if this doesn’t appeal, who are you? (A vegetarian or someone who prefers less excessive breakfasts? Cool, they’ve got you covered I think but I can’t vouch for the other options.)

IMG-20180515-WA0112  20180515_120616

Take a drive out to stunning Multnomah Falls! Sadly a fire destroyed a lot of the surrounding area in September 2017, so all of the hikes – and most of the scenic highway – in the area were closed last month. But there are a few just over the Washington border, or just drive around and see what you can find!


After you get sweaty (or if you never wanted to get sweaty in the first place), head to McMenamins Kennedy School near the Alberta Arts District for a soak in their warm, saltwater courtyard pool. (Closed on the first and 3rd Tuesday of the month, BYO towel.)


Bring in a drink from one of the bars, or check them out after. The Boiler Room was my favourite; pipes and radiators make up some of the railings and décor! You can also grab a drink in the tiny Detention Bar!

20180516_162316 20180516_173829

Stop on Alberta Street for a bite or a drink – there are tons of restaurants and bars to choose from. We loved the fried okra, curry, and décor at Bollywood Theatre. Salt and Straw is right there if you’re craving something weird and sweet (olive oil and balsamic with black pepper are two of their classic flavours)!

20180516_133137 20180516_134753(0)

Pack up and get ready to head to the coast!


*Bonus Day: Vancouver’s a sweet place to start if you have an extra day. Spend the day cycling, roller blading, or walking around beautiful Stanley Park. It’s a great place to bring a picnic, Frisbee, hammock, whatever! Or check out the aquarium!

IMG_3837  IMG_3841

Grab a drink in Gastown, then head to the Richmond Night Market – an easy Skytrain ride from downtown, and SO MANY food stalls to choose from! If you’re with a big group, skip the long line by buying a 6 pass and splitting the cost. Vancouver’s an amazing city that deserves a post of its own, so I’ll limit it to just these few ideas for now! I’m happy to give you suggestions if you’ll be in Van for a longer visit.

20180512_203620  20180512_201824