Traveling to Portland, Oregon

Portland is a beautiful city with tons of yummy restaurants, cute coffee shops, and wonderful shopping.

My mom and step dad have lived in Portland, Oregon for almost five years, and I’ve visited them well over 10 times since they settled there.  Portland is a beautiful city with tons of yummy restaurants, cute coffee shops, and wonderful shopping. It’s also a fun place for people watching.  You may have seen a Netflix documentary called “Portlandia”.  After seeing it, I believe it rings true; this city is truly a unique and interesting place.

Portland is an amazing city. Actually, it was one of the top three cities Tommy and I were considering when we decided to leave Wisconsin. The main thing that kept us from calling this place home was the weather. It rains, and rains, and rains some more. However, I will say that the rain isn’t a consistent heavy down pour; it’s more like a light misty rain. If you have the proper rain gear, it really isn’t that bad. Depending on what time of year you visit, I recommend packing a pair of rain boots, a raincoat, and an umbrella. The rainiest months are October-March.

I would now like to share some of my favorite places to stay, things to do, and restaurants to try in Portland so you’re well prepared before making a trip there.

Places to Stay:

  1. The Pearl District in NW Portland. This neighborhood is more upscale with a bunch of cute boutiques and coffee shops and only a short 15-minute walk to downtown. It is easily accessible to all public transportation and very easy to get around. Going north to south, the streets read alphabetically and east to west they are in numerical order – so it’s near impossible to get lost. The Pearl District area has a few hotels but you could also find an Airbnb or VRBO in the area!
  2. The Benson Hotel. This elegant hotel is closer to downtown Portland and has so much character. You will walk inside and instantly be in shock at how gorgeous the entrance is. There is a big chandelier, dark woodwork, a fireplace, AHHH I could go on and on. This would be a great place to stay for a little anniversary get away!

Things to do:

  1. Visit Forest Park. This park is one of the country’s largest urban forest reserves and has over 80 miles of trails for you to hike, run and take beautiful pictures! You must make it all the way to the top because it has a most breathtaking view. The red oak trees, vibrant green vines, and quaint little waterfalls make for some of the best scenic pictures.
  2. Tour Pittock Mansion. This is a 16,000 square foot, 23-room mansion that is open to the public to tour. You can either drive up to the top or hike there beginning on the Lower Macleay Trail in Forest Park. It also has a beautiful panoramic view of the city and on a clear day, you can see Mt. Hood.Picture of Mount Hood
  3. Visit Portland Japanese Garden. According to Trip Advisor, this is considered the most authentic Japanese Garden outside of Japan. For only $17 you can spend the entire day here while drinking Japanese tea and walking the paths of the garden.
  4. Spend the day In Powell’s City of Books. Powell’s Books is a chain of bookstores in Portland, but the flagship store is in the Pearl District. You will be blown away at how massive this bookstore is. I’m talking level upon levels, bookshelves upon bookshelves. There is a 99% chance you’ll get lost in here. Powell’s not only sells new books, but used as well, so you could leave having spent $20 but walk out with 15 new books!
  5. Portland Farmers Market – PSU. The first time I ever visited Portland, I went to this Farmer’s Market and my mouth dropped when I saw how massive it was! It is open year-round on Saturdays, with hours varying from 8:30 or 9:00am – 2:00pm right on Portland State University’s campus. There are hundreds of vendors with booths set up filled with fresh produce, hand crafted jewelry, and so much more. I’d recommend taking public transportation here because the parking isn’t the greatest.
  6. Shopping on 23rd Only a few blocks west of the Pearl District, lies the Northwest District, specifically 23rd Avenue. This street has actually been named “One of America’s Best Shopping Streets”, and there’s no sales tax in Portland, so enjoy yourself ;). Aside from the shopping, 23rd Avenue has arguably some of the tastiest restaurants in all of Portland. All this considered, it is also only a one- mile walk to Forest Park (referenced above).


If you are renting a car and staying in Oregon for a while, I’d recommend taking a little trip to the two places below.

  1. Multnomah Falls. Only a 30-minute drive from Portland and you will arrive at one of the most breathtaking waterfalls I’ve ever seen. The falls are over 600 feet high and only a short five-minute walk from the parking lot right off the highway.
  2. Cannon Beach. About an hour and a half away from Portland, this is right on the coast of Oregon and one of my favorite places to go when visiting my mom and step dad. They have a little house right off the beach and it’s the most peaceful place ever. If you decide to take a day trip here, make sure you stop at Camp 18 on the way and get their cinnamon roll. It’s about a foot in diameter and probably well over 2,000 calories, but totally worth it.Picture of the rocks at Cannon Beach in Oregon


Yummy Food to Try:

  1. Deschutes Brewery Portland Public House. If you have dinner here, you NEED to get the big pretzel with the warm cheese dipping sauce, I literally dream about this thing. And if you’re in the mood for a yummy burger – get the Elk Burger!
  2. Cheryl’s on 12th. We actually stumbled upon this and decided to give it a try. It will now be one of my go-to restaurants whenever I’m in Portland. If you’re lucky, they’ll bring out fresh beignets, which absolutely melt in your mouth. They’re known for their Portuguese fried rice, I’d highly recommend it!
  3. Blue Star Donuts. Portland is known for the iconic Voodoo Donuts, which if you’re looking for an Instagram worthy picture and a cool experience, I’d check it out. However, if you’re in the mood for a tasty gourmet donut, Blue Star is your place. If you ask the locals, this is what they’d recommend as well. Favorite Flavor: Buttermilk Old-Fashioned
  4. Stumptown Coffee. If you meet someone from Portland, they won’t be able to stop raving about this coffee, they’re pretty proud of it. Like a parent watching their child preform a solo in a choir concert, proud. Founded in Portland, Oregon, this coffee is now sold all across the country. I got the almond milk latte and it was ahhhhhhhmazing!!!!Picture of an Almond Milk Latte from Stumptown Coffee
  5. Tea Bar. This is a stop I make every time I’m visiting my mom, and in the winter months my go-to drink is a Golden Milk Coconut Latte, and in the summer, I like the Vanilla Rose BOBA tea with unsweetened almond milk.

If you travel to Portland and stop, stay, or eat at any of these spots, tag/email me and let me know what you think!

Until next time.

Peace & Love,

Asset 5




Share this post

keep reading, friend

Scroll to Top

This website uses cookies to ensure you get the best experience on our website.

girl, Get the guide.

Get my No Equipment Home Workout Guide!