Traveling with Children to Portland for the Weekend


When thinking about getting on a plane with two 4 year olds and flying 5 hours across the country just to spend 2 days hiking and then repeat it all over again to get back home, most moms would start hyperventilating. It’s true, preschoolers aren’t the easiest to hang out with in general, then put them in a tin can for hours straight and the resulting nightmare can give anyone a heart attack. Between the why’s and the constant whining and the snacks and having to sit still for 5 hours, you would think that the majority of sane people do not plan short stints across the country. And we say they are missing out!


Always An Adventure with Kids

There is something to be said about being spontaneous and teaching your child to love travel and the discovery of new places, no matter how inconvenient it might be at times. They say it’s the journey, not the destination, but we say it is absolutely both. When traveling with small children, just the process of getting to the airport, going through security, finding a gate, boarding a flight, and going over the safety information presents so many learning opportunities. To us, it’s the same old thing, to them it’s fascinating.

So a few months ago, when it was still warm and pleasant, myself and one of our editors, Dani, grabbed our 4 year olds Lexi and Eli and embarked on a short but one of the most memorable trips of the year, the discovery of Portland.

My daughter Lexi still says to this day when she sees something beautiful, “This is beautiful. Just like Portland.”

The flight itself was a blur. Not too bad; I think the kids spent most of the time snacking and playing on the iPad, with only short stints of questions. “Shhhh, Mommy is tired right now.”

When we arrived, we easily rented a car with two child car seats in it and tested our knowledge of proper car seat installation. The times of relying on our husbands to install a car seat are over. This is the new stage of “I can do everything myself” even if your whole life someone did this particular thing for you. It also helps that we work for Daily Mom. I mean, it would be quite shameful not to know how to do it, right?

Checking in to Portland

We drove to the Gresham area where our Hampton by Hilton was located. A note about our hotel: We needed to have a place that was clean, comfortable with big rooms, friendly staff, but also didn’t cost us too much. We are in town for 2 days, and we will be spending 99% of our time outdoors. The hotel we picked had to be reliable and familiar. A 3 night trip isn’t the time to risk a wrong review on Expedia. Hampton by Hilton was a no brainer. There were three in the Portland area, but the Gresham one seemed to be in the best location to remote places and Portland itself. So we went with that.

The first thing we did upon arrival was go to the hotel gym. It’s kind of awesome when you travel with someone with the same interests. Our kids sat in the corner and snacked and we worked out. Soon they were bored and wanted to try out the bike and the treadmill. And when we moved to weights and the cable machine, they promptly asked us to show some exercises to them. Another teaching opportunity.

I think gym time ended when Dani dropped a weight on some body part and we decided maybe it was enough.

Two guesses what happened upstairs in the room when we finally made it to our beds? Yup, the only thing a child can do upon check in. Test out the strength and bouncy qualities of the beds! We used the coloring books and little gift bag given to us by the staff upon check in and went to bed ready for our next day’s adventure.

Our Favorite Places

In the morning, after having a nice breakfast in the lobby, we set out to find the Trail of Ten Falls in Salem. The drive itself was gorgeous enough to want to take it, going through farms and wineries while our children exclaimed about rollercoaster roads and how beautiful Portland is.

“Mommy, I want to live here. It’s my favorite place! What’s it called again?”

Eventually we made it to the park and stopped over by the map to try and figure out which entrance to take. Locals didn’t seem to know anything about a Trail of 10 Falls. We spent an hour walking in the fields and the woods, gathering flowers, playing with our children, and taking photos. The weather was amazing. Finally, when every last dandelion was blown, we continued going in hopes of finding the right entrance.

Eventually it happened; we paid the entry to the park, asked around where exactly to go, and set off on a hike hoping our 4 year olds would have the stamina to walk such long distances. The first waterfall was majestic. We walked behind it over a bridge and just smelled the air and watched it fall.

The kids were happy to climb the rocks all around giving us micro heart attacks. After a little bit we walked back down to the waterfall pool. Technically visitors weren’t allowed in the pool, but this is all about adventure and pushing limits right? So we hopped the fence and joined a few other rule breaker families in the walk down to where the waterfall meets the ground.

On the way back up to the main area where we would walk to the other falls, we encountered some whining. I think it was lunch time, so we stopped at a cafe with nice flatbreads and sandwiches and allowed the kids to run around with the other kids playing hide and seek. It was strangely peaceful. Here we were literally in the opposite corner of the country (we live in Florida and North Carolina), relaxing on wooden chairs while our kids were mingling with some locals.

After a little bit of rest, we set out to see the rest of the waterfalls on the trail. The kids’ favorite part of the hike was the fun trail that was almost like an obstacle course. We found fallen logs that served as balance beams, stumps that were oh so fun to jump on and see who’s taller, and huge double trees that turned into houses and hide out spots. It took us hours to get through the trail (pack lots of snacks!), but I don’t think I have ever seen our kids that excited to be out in the woods.

After a day of running around, we were happy to return to our comfy Hampton by Hilton and our beds with some take out from a local asian restaurant and have a very solid night of sleep.

Day Two started with a plan to hit the most famous attraction in Portland, Multnomah Falls. This majestic, grand waterfall draws in thousands of visitors a day, and the place is always crowded. However that did not keep us and our children from enjoying the grandeur of the natural wonder, taking photos, and hiking up to the top. We even bought a few souvenirs.

After getting our fill of waterfalls, it was time to eat and explore downtown Portland. We loved having dinner at the French restaurant set in an old Victorian house, Paley’s Place, run by a Russian chef (how perfect is that?! I’m Russian if you didn’t know!)

After that, we were ready for the WEIRD, that is downtown Portland. “Keep Portland Weird” isn’t just a saying, it’s a true lifestyle. Downtown Portland is clean and a pleasure to walk through, with a mix of old and new. People watching is probably the number one activity for tourists here, which we certainly did.

We got to dance on the corner with a very talented young man drumming on paint buckets (phenomenally), we got to talk about life and war and parents and superheroes with a homeless man, and we ordered and ate way too many Voodoo donuts, because… well, Voodoo Doughnuts.

All very enriching experiences, with the latter one being only enriching to the taste buds if we are honest.

The day ended the same way it did the day before, by us passing out on our comfortable beds at Hampton by Hilton.

Fast forward to the next morning and check out time; we got sent on our way with some refreshing bottles of water from the front desk and another map to help us finish off our trip with a bang.

That bang was ROCK CLIMBING. Obviously, Portland is known for its active outdoorsy inhabitants, so we couldn’t leave the area before we had a chance to check out at least one of the rock climbing gyms. It was Dani and Eli’s first time experiencing rock climbing and those two were hooked, just like Lexi and I already were. We spent more time climbing than we should have considering our flight departure time, but it was amazing! Afterwards, we grabbed a quick and healthy snack at the cafe in the facility and were off to the airport.

As you can see, despite only having two full days in Portland and two four year olds in tow, we managed to do quite an array of activities and explore the area enough to leave us with unforgettable memories.

If you are considering taking a spontaneous trip solo or with your loved ones, do not hesitate. Nothing is more precious than the experiences and memories you encounter along the way. That is the spirit of the Seekender, to learn, explore, take opportunities, and get away. Take a weekend and see how amazing it feels to just be somewhere new!

Elena, Daily Moms managing editor, is part of the Ultimate Seekender team. Elena has a travelers soul. She just cant stay in one place and takes off on adventures every chance she gets. While she does travel on her own, her passion is traveling with her daughter so she can experience as much as possible. As part of the Seekender Team, Elena has been bringing you travel posts to motivate and inspire more family travel. Here you can learn more about the Seekender movement.

Follow the Ultimate Seekender Team with #seekender. What are you waiting for?

Do you want more inspiration for planning a weekend getaway? Here is Why You Should Take Weekend Getaways5 Fantastic Family Weekend Getaways, and How To Plan A Weekend Getaway.


Photo Credits: everyavenuegirl




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A Russian by birth, Floridian at heart, Elena's favorite pastimes are traveling, photography, volleyball, reading business, psychology and parenting books and finding cool products. Elena started Daily Mom with a vision to provide quality content and help to busy modern women. Follow her life and adventures with her 7 year old daughter at Every Avenue Life and Our Little Voyages. or on Instagram at: @everyavenuelife @everyavenuegirl @befitandtravel @ourlittlevoyages

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