Welcome to Portland – one of the coolest and weirdest places to live in the US!

If you are planning your first visit to the City of Rose (Portland’s nickname), you might wonder how it feels to be there for the first time.

One of 550 rose varieties at International Rose Test Garden, Portland
One of 550 rose varieties at International Rose Test Garden, Portland

We felt the same a couple of years ago when we’re looking through articles with titles like: “Best cities to raise a family”, “Best places to live”, etc. Portland held high positions on many of them, named one of the most eco-friendly, family-friendly and bike-friendly US cities.

Bike traffic in Oregon
Bike traffic in Oregon

After multiple visits, I can tell you it’s all true and even more: Portland is eclectic, cozy, incredibly green with tons of recreational opportunities so easy to hit. You can be whoever you wanna be in Portland, with a rare chance to catch a sideways glance.

Keep Portland weird. photo credit: stumpedinstumptown.com

This post is for parents, who want to discover Portland, making sure that their kids will also have a great time. We always plan our trips around our plans, mixing in cool ideas that kids will be excited about.

Best time to visit Portland

There is no “best time” to visit Portland. It’s all based on your desires, what you want to see and do. Summers are usually very sunny, dry and sometimes really hot, while winters are mild with a rare chance of temperatures dropping below the frizzing point. The rainy season lasts from October till May, so be prepared for gloomy weather during those months.

Wandering the streets of Portland
Wandering the streets of Portland

We prefer to explore new cities outdoors. Our second visit to Portland in September brought us much more joy than the first one at the beginning of December. In September, the days were longer, dry and very sunny.

Rainy and cold, but still cool: Portland Saturday Market
Rainy and cold, but still cool: Portland Saturday Market

How to spoil your visit to Portland

Truth be told, Portland is a city where you’ll have to try really hard to spoil your visit there. It’s a beautiful, family-friendly place, full of all kinds of activities: lovely gardens, dozens of parks, museums, galleries, roasters, breweries, and great eateries where visitors with kids feel welcome. Nevertheless, after our second trip, we learned a few things that I wish somebody told us before.

During our first visit to Portland, we felt like this goat: sad and completely wet. Oregon Zoo
During our first visit to Portland, we felt like this goat: sad and completely wet. Oregon Zoo

Only stick to “kids-will-love” places

Period.

Not going out of town

Oregon is home for multiple nature wonders, with some within just half an hour drive from Portland. It’s roughly like driving from one end of the city to another! Do take a drive through the spectacular Columbia River Gorge and visit at least a couple of waterfalls there. It’s very worth to spend there from a couple of hours to a full day, if not longer.

Columbia River Gorge region
Columbia River Gorge region

Multnomah Falls is the tallest, most popular, and most crowded waterfall in the area. It is not the only one, though. There are more than ninety waterfalls. They are all different and many of them require little or no hiking, are not crowded and easily accessible by car. You just keep driving a couple of minutes from one place to another along the Gorge. Check for possible closures or wildfires here before you go.

Multnomah Falls, the second tallest year-round waterfall in the US. Oregon
Multnomah Falls, the second tallest year-round waterfall in the US. Oregon

Come early in the morning or late in the afternoon to beat the crowds if you plan to visit Multnomah. Watch kids closely while visiting Columbia Gorge: there are plenty of slippery places and some exposed cliffs.

We spent an entire day at the Gorge (we also made a tour at the Bonneville Lock & Dam), hiked several easy trails and saw so many completely different waterfalls.

Two hidden gems worth your time and effort: Horsetail Falls hike and Lower Oneonta Falls hike. We almost did this latter one, but in December the water was too cold to wade in to get to the waterfall. It will make an exceptional summer hike, though.

One of the many waterfalls at the Columbia River Gorge, right at the car pull-out
One of the many waterfalls at the Columbia River Gorge, right at the car pull-out

Underestimate the weather

If you are coming during the rainy season (October – May) you should be properly geared up. While most of the time it only drizzles, heavy rain can occur, sometimes unexpectedly.

Gear up for a rainy day in Portland

Waterproof boots, waterproof jacket, umbrella, and sweater – you don’t need to carry all of that around, but it’s good to know you can pull it at any time you need. Electric shoe dryer takes up very little space but can save a day (it did for us and our 4 pairs of shoes). The first and only time our son was whining about how cold he is, happened in Portland when all of his “waterproof” clothing was soaking wet in just half an hour.

Rainy day at Portland Zoo
Rainy day at Portland Zoo

Where to sleep in Portland (and how to spend a night at a former elementary school)

Our most favorite options to look for accommodations became Airbnb/VRBO (for personal experience and meeting the locals) and Priceline (best hotel deals).

After returning back from the trip, I found this local gem that I would love to try for lodging next time: McMenamins Kennedy School. It sounds weird but true: a hotel located in a former school! Add a heated pool, free theater admission, a bar, a restaurant, and all of this surrounded by “not your ordinary hotel” design. It seems like the price is worth the experience.

McMenamins Kennedy Elementary School, Portland
McMenamins Kennedy Elementary School, Portland

Where to eat in Portland. Kids-friendly Brewery

Portland can be your next foodie destination. There are so many places to have a unique experience of any kind and diet, you’ll be surprised! Since two of our kids were very small at the time (1 y.o. and 4 y.o.) and usually behave like normal, happy kids (read: loud, moving around instead of sitting still like little Buddhas and waiting quietly), most of the time we stay away from any eateries.

During our last visit, however, we felt like we just had to visit a local brewery and treat the adults with the craft beer Portland is so famous for.

Hopworks Urban Brewery, Portland
Hopworks Urban Brewery, Portland

We had a great experience at Hopworks Urban Brewery. Besides the good food and a huge beer selection, it was the most kid-friendly place we have ever visited. 3 playing areas, toys, huge magnetic chalkboards – kids went bananas when they saw all of that.

Hopworks Urban Brewery, Portland
Hopworks Urban Brewery, Portland

Laughing Planet is another worthy place to visit with little ones, especially with picky eaters, like one of our kids. Large varieties of kid styled healthy meals, fast service, and reasonable prices. The place is very spacious and has tons of dinosaurs to play with =). Both places located on the Eastside of Portland.

Kids meal at Laughing Planet

Being in Portland and not trying local doughnuts is a crime! We don’t usually buy doughnuts, but in Portland, it’s hard to resist. They look like a small weird piece of art.

We tried Nola Doughnuts and Voodoo Doughnut. Both are located on the Westside of Portland.

Nola is great for adults: texture and tastes are pretty unusual and melting in your mouth. Cajun Maple Bacon we liked more than anything else.

Nola Doughnuts

Inside Nola Doughnuts, Portland:

Nola Doughnuts, Portland
Nola Doughnuts, Portland

Voodoo Doughnut was great for kids: the dough tastes like regular doughnuts but for design and doughnut names the creator’s imagination went wild. These doughnuts are huge. One is more than enough to feed an adult, not speaking about a child. Great prices.

Inside Voodoo Doughnut, Portland
Inside Voodoo Doughnut, Portland

15 Things you should try while visiting Portland

Some of the places in the list below are not designed specifically for kids, but are family-friendly and were experienced (and enjoyed) by us and our 1-, 4- and 9-years-old kids.

City views from Portland aerial tram
City views from Portland aerial tram
Supadupa Marimba Bros at Saturday Market, Portland
Lan Su Classical Chinese Garden, Portland
Lan Su Classical Chinese Garden, Portland

Must-see places in Portland on map

Thanks for reading and happy traveling!

Erika with Voodoo Bubble doughnut
Erika with Voodoo Bubble doughnut