The Ultimate Guide to a Weekend in Portland, Oregon

“Portland? Why are you going to Portland?” That was the comment I got when I mentioned our weekend trip for Veteran’s Day Weekend. But my husband was turning fifty, and since we had to postpone his big trip, I wanted a quick weekend getaway for his big day that we could do on points.  Portland met that bill and turned out to be a fun weekend away that was entirely unexpected. We found a fantastic food scene, a quirky city with unique neighborhoods and friendly people, and great independent shops and restaurants. But most importantly we just felt relaxed, welcome, and comfortable in this city by the Columbia River. Check out what you should do to get the best out of a weekend in Portland.

*Disclosure: This post may contain affiliate links that allows me to earn a small commission at no cost to you. I only link to products I would or have used myself and all opinions expressed here are my own. You can read the full disclaimer here.

A father and his children in front of the White Stag Portland Oregon sign

What to Do

See the Waterfalls

The Multnomah Falls

Just outside Portland at the Columbia River Gorge, there are numerous waterfalls and hikes in this stunning National Park. You can drive on the Historic Columbia River Highway, the historic road built for road trips back in 1922. You can stop at Crown Point Vista House, a rest stop that was built in 1918. It gives you the best views of the river and the gorge. But you will of course want to see the Multnomah Falls. These are the famous double falls that you see in all the pictures of Portland and the Columbia River Gorge. There are some excellent views and some good hiking near there. But be sure you stop and see some the of the “smaller” falls such as Horsetail Falls, the Shepperd Dell, and Wahkeena Falls. The Latourell Falls were my favorite. You can get there by renting a car and driving or booking a tour. We used Get Your Guide to book Wildwood Adventures, which picked us up in a van, took us to the best falls, and then drove us back to central Portland.

Do a Walking Tour

A mural in Portland Oregon

If you have been around (the world with kids) any amount of time, you know I love a good walking tour. Portland is a city that had some surprising rich history, both as a frontier town from the early 1800s, to more modern history as the founding of the hipster and Black Life Matters protests. However, you don’t know the rich history unless you are walking around. We found out that there was a public arts program that paid for sculptures all over the city, including a strange one in Pioneer Square which told the weather every day. We found out about Bud Clark, who famously allowed a poster of himself appearing to flash a statue later became a well-known and respected mayor of the city. Portland has several different neighborhoods, and you need to walk and explore them to understand them. We Used Get Your Guide to book a tour with Side Dish Mafia to combine our two favorite activities, eating and walking!

Visit Powell Book Store

A young person reviewing the books on the shelves at Powell Bookstore

When people tell you you can spend all day in Powell Book Store, believe them. This is the largest independent bookstore in the world. It has three floors, ten color-coded rooms, and thousands of new and used books to fill your basket and suitcase. I spent most of my time in the Red room (Travel), my husband in the Pearl room (Science) and my kids in the Pink Room (Young Adult). But I did make it up to the Rare Book Room. They only have so many passes, so you need to be patient waiting for one. But once you enter, it is an amazing room filled with rare and old books. First editions, old comics made in the 50s, and even some books hundreds of years old. Most are behind glass, but they had a few out that you could look at and (very gingerly) flip through. We as a family tried to only buy a few books, but we could not help ourselves. We took advantage of their low-cost shipping options to have the books shipped home for us.

Check out the OMSI

The entrance into the OMSI

If you know us you know we also like a good museum. The Oregon Museum of Science and Industry (OMSI) is right across the river from downtown. It is your typical science museum with fun interactive exhibits. We got to experience their special exhibit on Orcas and it was fun to see the giant orcas, and the rooms they used screens to make you feel like you are in the ocean. We saw some great films, and learned a lot about how orcas became part of water parks and the work that is being done to reduce orcas in captivity. There was also a nice exhibit in the Natural Sciences room on Defenses of the Animal Kingdom, where we learned a lot about the natural defenses of animals, and even saw a Sloth. But a favorite part (which for us almost always is) was the planetarium show, where we got to watch a show about black holes on the domed screen. Outside was a to scale model of the lunar space shuttle that the kids got to climb in and try out.

Do Some Shopping

Two teens shopping in a store

What’s my favorite activity after travel, shopping!  And in Oregon there’s no sales tax! In downtown there are several luxury brand stores due to the lack of sales tax. But this is the headquarters of Columbia and Adidas, and both not only have their flagship stores, but employee stores that sell things discounted and almost anyone can actually shop from. Sadly, we didn’t get a lot of time to shop this trip, but I did buy myself a new phone once I realized I would be saving hundreds on sales tax.

Eat at a Food Truck

A young girl eating a sandwich in front of a food truck

Saving the best for last. The food scene in Portland is unreal. I had heard that there was a huge food truck culture, but I began to really understand once I was there and on the food tour with the Side Dish Mafia. The city has designated areas called pods that made it easier for people to open these food trucks. They had less initial start-up costs than restaurants and because of this they flourished. There are two types. There are the ethic stalls, where you get a large selection of a specific ethic food at a low price. Think of the Halal carts of New York, or the taco trucks of Los Angeles. But there are also more niche trucks, and those are growing even more. You can get gourmet egg sandwiches, mini donuts cooked fresh, juices, or even a beer!  You need to make sure to hit up a pod and try food from a few different places.

Where to Eat

A burger and fries, coffee and croissant, chocolate, and a Chicken Katsu sandwich

The food scene was top notch in Portland, and we had a hard time picking what were our favorites because we didn’t have a bad meal in Portland. But here are a few of our favorites.

Coffee: Stumptown Coffee RoastersThis local to Portland Roaster has the most amazing coffee. And, for those dairy free like me, they’re base milk is oat milk. Don’t worry, they also have almond, soy, and cow (for those who want that sort of thing). They also had the most amazing pastries, including a fluffy croissant that was reminiscent of Paris mornings.

Breakfast:  Grits & GravyThis Black Owned Business in downtown has stick to your ribs Southern Fare. You can get chicken and Waffles, grits and eggs, thick pancakes or French toast, and other great food. You can also get Café On Monde Chicory coffee from New Orleans and dessert if you have any room left in your stomach!

Lunch:  Hal’s Café in the McMenamins Crystal HotelMcMenamins is a quirky brand all over Portland, and we hit up the Hal’s Café for lunch one day. Everything we ate was good. I had a plant-based burger with Chao, and it was one of the best I’ve had and the cheese actually tasted like cheese! I also had these truffle French fries that was crispy and full of umami. My husband had a Bloody Mary that was filled with fun vegetables and spice on the side, this place really hit the spot.

Dinner:  MarrakeshHave an event you are celebrating and want a good meal that also includes an experience, then Marrakesh is your best choice! It’s Middle-Eastern food and they offer a five-course meal. It comes with warm, delicious lentil soup, a salad filled with couscous, raisins, and vegetables, B’stilla Royale, packed phyllo dough filled with meat, and then an entre of your choice and dessert. We went for the feast which gave us four different entries. We all loved the lamb and the chicken with honey and prunes. All of this happens in a traditional Moroccan setting with low tables and cushions on the floor. But that’s not all. On the weekends, they have belly dancing, so while you are eating, you are entertained by an amazing dancer who uses scarves, knives, and other props. It was the highlight of the trip.

Drink:  Rachel & RoseEver want to experience drinking on the Night Bus in Harry Hotter? That’s what coming here is like. It’s a bar in a double decker bus permanently parked on Burnside Street. They have an excellent selection of beers, but they also have soda and Butterbeer for the kids. Get a drink and sit at the top to people-watch.

Dessert:  Azar IndulgencesMy husband hates dark chocolate. He’s been a milk chocolate person all his life. After tasting the selection of dark and milk chocolates at Azar’s place, he declared he never knew dark chocolate could taste so good. Azar has worked with her father to create small batches of chocolate that is delicious in all forms, but she is careful to pick the forms. In her small shop you can get all different chocolates, but you can also get some amazing drinkable chocolate. This isn’t hot chocolate that you get someplace else. This is a thick, rich, drinkable chocolate drink, made with oat milk so it’s safe for all! We loved this place so much; we went twice and brought all our presents there.

Food Truck:  Fried Egg I’m In LoveThis was a hard one to pick, but if you can only visit one, visit Fried Egg I’m In Love. This truck does egg sandwiches all themed to different songs. We had the Yolko Ono, filled with yummy pesto, a handmade sausage patty and a a lovely gooey fried egg. But you can also get the “Smells Like Protein Spirit” if you are Nirvana Fan. The sandwich was rich and filling, and one of the best things we ate on the Side Dish Mafia food tour.

How to Get Around

Walking: Getting around Portland walking was fairly easy. It’s not a hilly city like San Francisco and the downtown area is fairly compact. It’s also fairly safe. There are a few areas where you will find a homeless population, but similar to other cities, stay on well-lit streets, don’t bother them and they won’t bother you. There weren’t moments when I felt unsafe walking.

Public Transit:  Portland does have a bus and light rail system. To be honest, we didn’t take advantage of it since we had a short amount of time and it was the four of us, so we tended to walk or take a Lyft. But it’s low cost, convenient, and you can load up a pass on your phone wallet.

Ride-Share:  We were in the city for a short amount of time and always running late, so we tended to ride-share. It was safe and convenient, we never waited more than 10 minutes for a Lyft. Considering it was four of us, it was often not much more than public transit (depending on the distance).

How to Get to Portland

The wing of an Alaska Airlines plane over mountains

Road Trip – Portland is right at the intersection of I-5 and I-84 making it an easy (if long) drive from California, Washington, or Idaho

Train – Amtrak goes through Portland, and all the Amtrak Northwest Routes go through Portland Oregon. If you are taking a train up from as far south as Los Angeles, and as far North as Vancouver, British Columbia. But it also the rare connection to a East/West route, being able to come all the way from Chicago, IL. 

Flight – The airport code for Portland is PDX and this is how we arrived. We flew Southwest, and there are many flights from most of the West Coast. Portland is also a secondary hub for Alaska Airlines. It is a clean, quick airport with easy access to ride-share and a nice children’s play area.

What to Bring / Wear

A family of four in front of a waterfall wearing rain gear
  • Waterproof Gear: If you are planning to hike near the falls bring some waterproof gear. Even if you are just walking near them, the mist can get to you. We didn’t do any strenuous hiking, so sneakers were enough for us, but I did have the kids bring their raincoats. My husband and I choose our 32 degrees packable down coats instead. My son loved his new Columbia rain jacket. 
  • Comfortable Shoes: Portland is a walkable city, but if you don’t have comfortable shoes, your feet will be unhappy at the end of the day. I had my trust Rothy’s sneakers, but during the hike I wore my Sketchers sneakers with more grip. My husband and kids went with their Sketchers Go Walks.
  • Weather Resistant Jacket: Portland, like Seattle, has a lot of rain, but it’s that misty rain as opposed to heavy rain. Make sure to bring a water resistant or waterproof coat to keep yourself warm and dry, this is where all our Columbia rain jackets came in handy.
  • Reusable Bag: Portland has a plastic bag ban and a fee for paper bags. Bring a reusable bag for your purchase and books you are getting at Powell’s. I love a bag that folds up and fits in your day purse.

Portland might not be your first thought as a weekend getaway. But if you are in the mood for a laid-back city where you enjoy great food, fun days, and beautiful nature just outside the city, then Portland’s where you want to go. We loved our time in the city and look forward to returning soon.

The Ultimate Guide to a Weekend in Portland, Oregon

2 responses to “The Ultimate Guide to a Weekend in Portland, Oregon”

  1. […] was the answer I got from my husband when I sent him a list of tours we could do when we were in Portland, Oregon for his birthday weekend getaway. Food walking tours in my opinion are the perfect way to get to […]

  2. […] But I wanted to do the opposite of the advice, I wanted to chase the waterfall. We were headed to Portland, Oregon, and every blog post I read on the city told me that you had to get out to the Columbia River Gorge […]

Leave a Reply to Teens And Treats: Checking Out the Food Scene in Portland with Side Dish Mafia | Around the World with KidsCancel reply

I’m Robin

Hello, I’m Robin, the founder of Around the World with Kids. I’ve been traveling since I was 10 months old and refuse to stop. Luckily I found a husband who will indulge me. Now we travel near and far with my two young children, and write about our journey to help inspire you on yours.

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