Road Trip: Bay Area to Portland with Kids

We’ve already covered the first leg of our trip – the San Francisco Bay Area to the Oregon coast – and now to the main attraction: Portland. While it sounds like we ate our way through Portland, we did. Although we did a lot of walking in between to make up for it…or to kill time before our next meal.

Getting to Portland

We spent two nights in Gold Beach before driving up 101 to Highway 38 to I-5. It’s an easy, but at times boring driving that takes a little over five hours, not including our two usual stops.

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Dean Creek Elk Viewing – You may blow past this place, wondering why there are cars pulled off the road, but then you see the elk, out there chillin’ in a pasture. This is a quick and fantastic spot to pull off the highway, stretch, check out the elk, and the bonus is that there are clean bathrooms.

Eugene – Eugene is a great place to stop to either grab a bite or swing through the home of the University of Oregon. On our way to Portland, we like to stop for lunch at Newman’s Fish Co. for the best fish and chips. They’re even more phenomenal that you image coming from the side of a store, adjacent to the parking lot. On our way home from Portland, we always stop at Eugene’s Voodoo Donuts. The Portland Voodoo Donuts always have a line, but the longest line we’ve found in Eugene has one person ahead of us.

Outlet shopping! Woodburn Outlet Mall is a must stop. Oregon is famous for not having sales tax, which makes the prices even better than we’d find at home. In fact, one time at the Gap outlet store, the sales clerk asked where we were from, then said, “Enjoy our low prices!” That same phrase was repeated to us at a restaurant in Portland and it’s true, Oregon feels like a bargain compared to the Bay Area. We did enjoy their low prices! Woodburn has a North Face outlet, which is always our first stop when we arrive.


Where to Stay

There are definitely more quirky and plush places to stay, but we like the Hilton Portland & Executive Tower. Our first visit was because everything else seemed booked, but our second visit was because we found the central location and in and out parking worked well for us. Stay in the executive tower because that is connected to the parking garage, allowing a bypass of valet. There is an indoor pool, which is small, but big enough for the kids to have fun.

What to Do


Sauvie Island – Sauvie Island is perfection. There are beaches, fruit picking, and seasonal festivities, like corn mazes and pumpkin patches that open Labor Day weekend. Sauvie Island Farms is beautiful and huge, much bigger than the u-pick places we’ve been to in California. They had a great variety and pretty flowers, but because we were traveling, we stuck to the peaches. We were told they were for canning, but they tasted great.

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Portland Aerial Tram – The tram was closed for maintenance during our first time in Portland, but we made it on our second time. It’s a slow gondola ride from lower Portland to the upper Oregon Health & Science University campus. Bring your camera because not only is the ride beautiful, OHSU boasts of incredible views. On a clear day, Mount Hood and Mount St. Helens are in clear view. 

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Street haircuts at Bishops Barbershop – It wasn’t really on the street, but it felt like it because the place was so opened up to the street. I saw the sign for haircuts and beer, and was confused, but interested because school was coming up fast and we hadn’t been able to get haircut appointments. Bishops, which I called Hipster Haircuts, was our savior. And they offer free beer with a haircut. (The beer wasn’t for kids, obviously.) Saturday night entertainment and a haircut, all in one. Awesome.

Jamison Square Fountains – We scored a fabulous parking spot near the Jamison Square Fountains, but our kids took one look and said no. Too old, I image as this looked like a little kid paradise. We saw tons of little ones wading in the fountain while parents looked on. Our kids are too cool for school.


This usually isn’t our thing while on vacation, but again, Oregon has no sales tax (holla!) and who can deny themselves a City of Books, and quality art supplies? Not us, anyway.

Powell’s City of Books – Powell’s is a must visit, by law, I think. Before we left on our trip, someone asked my son where were going, and he responded, “To a city of books!” The kids went wild scoping out all of the comics, graphic novels, and other books they love. I like having the option of either new or used, especially when it’s a second copy of the Calvin and Hobbes book we already own (one per kid).

Dick Blick – There’s one in Berkeley, but that may as well be hours away. Our kids loved walking the aisles at Dick Blick, dreaming of the possibilities. We went in to get back ups of my daughter’s cartooning and drawing gear, and we may have walked out with a tad bit more.

CargoCargo is right around Powell’s and Dick Blick downtown, and it’s the funkiest store with all kinds of interesting imports and trinkets.

Missing Link Toys – My kids loved Missing Link Toys. It’s a lot like Kid Robot in San Francisco, with slightly lower prices.

Where to Eat

Food trucks are awesome in Portland. They’re great in San Francisco, too, but here they move, while in Portland, they take up empty lots and set down semi-permanent roots, making them easy to find. In many places, it’s like a quality food court.

Cheese & Crack Snack Shop – the place so nice, we ate there twice…and we would eat there all the time if closer. Since we were last in Portland, Cheese & Crack has moved up to a stationary place and has expanded their offerings, but we visited before, when they were a cool little shed-looking truck off of an alley. This is the best food, a fabulous concept, and it’s a great price. There website says a “kid is to candy shop as adult is to Cheese and Crack Shop.” This is TRUE! This place is a must stop, even if only for a snack.


The Grilled Cheese Grill – We ate the best grilled cheese sandwiches ever in a double decker bus. How is that for memorable? The kids both had The Kindergartener with bacon, I had The Gabby, and Kevin had something else. He was going to order an Original Cheesus, but made a specialized order. Maybe with bacon and jalapenos? I cannot remember.

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Pine State Biscuits – It’s worth getting up and out there early. It’s hearty and so very good. I can’t remember which biscuit sandwiches we ordered, but they were all good. Plus, Stumptown Coffee!

Slappy Cakes – Alicia of Posie Gets Cosy had mentioned the make-your-own pancake place before, and I knew it was a place my kids would love. They devour pancakes, and adding the griddle on the table aspect was exciting for them. We picked two batters for the four of us – regular and peanut butter – and it was the ideal amount. For toppings, we selected chocolate chips, butterscotch chips, and bacon. Away we went, making little silver dollar pancakes where the kids experimented with different flavor combinations. It was tasty fun. Get there early or expect to wait. We arrived soon after opening and the wait was minimal, but it filled up super fast.


Lardo – We hit Lardo at a bad time for us. We were hungry, it was busy, my son, and our mostly vegetarian, announced he hated the menu and wouldn’t eat there. Somehow our order got confused and while we ordered three cold fried chicken sandwiches, only two showed up, which ended up being sufficient. We split it four ways, and with a side of fries, it worked fine. The chicken sandwich was fabulous and the fries had a great herb flavor. Next time we’ll try again with out a mostly vegetarian.

¿Por Que No? – This was my favorite place we ate, hands down. There was a long line, and we felt lucky to find a seat, but it was so, so worth it. Why don’t we have a place like this in the Bay Area? I had the chorizo taco and a calamari taco and pomegranate margarita. It was perfect. The only thing I would have done differently is order for our daughter from the adult menu. The kids menu burrito was small, and because the line was long, she was stuck with un poquito burrito.


Voodoo Doughnuts – The kids thought they were dreaming when I said we were getting doughnuts, but when they saw the doughnuts, they didn’t know what to think. They’re huge and crazy, with topics not at a corner donut shop. Tips: Skip the downtown location and head SE. That shop still has a line, but it’s much smaller because not every tourist or drunk college kid knows about this location. On our way home, we stopped at the location in Eugene, which did not have a single person in line. We walked right up. Among the doughnuts we ordered and mostly shared over two visits: Grape Ape (surprisingly good), Voodoo Doll (the kids loved it), bacon maple bar (winner), The Loop (Fruit Loops), Dirt Doughnut (Oreos), Marshall Matters (M&Ms – it was like eating a cake), Butterfingering (saying it outloud is the hard part), and the best: Old Dirty Bastard (chocolate, Oreos and peanut butter. get a fork for that one).

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Salt & Straw – Really good handmade ice cream with unique flavors (hello, bourbon! Chocolate Chip Mint Julep, too!). There will be a line, regardless of the time, so expect to wait.

Ruby Jewel – They sell their ice cream sandwiches at our local Whole Foods, and when we stumbled over the scoop shop in Portland, we had to stop for dessert. It was a great end to our night.

Waffle Window – We may be in the minority, but while we liked this place, we weren’t in love with it, and most people are in love with it. A chocolate dipped waffle is great on a hot night (they’re served chilled).

Burgerville – we stopped at a Burgerville on our way home through Oregon. People compare it to In-N-Out, but it’s no In-N-Out. It was fine, healthier than other options, and definitely kid-friendly. One thing I noticed was that there were many kids at Burgerville, but only one with a soda. And she belonged to me. Good work, Oregon.

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