9 of the Very Best Things to Do in Portland Oregon

The Pacific Northwest is at its best in the late spring and early summer months! I recently had a chance to visit the city while attending my first TravelCon and came up with this list of the best things to do in Portland Oregon!

This post may contain affiliate links. These links provide a means for sites like NattyGal.com to earn a small commission when a reader clicks through and makes a purchase at no additional cost to the reader. See full affiliate disclosure in Privacy & Disclosures.

The Best Things to Do in Portland Oregon

1. Relax in Pioneer Square

Pioneer Square is a great launching pad sight for all things Portland. As you approach Portland’s living room, you’ll see the lovely Italianate Pioneer Courthouse which was completed in 1875. To this day, it remains the oldest still-existing federal building in the Pacific Northwest.

Walk around the square taking in the eateries, the milepost sign, and the exquisite wrought-iron gate that once marked the entrance to the Hotel Portland. You may also notice the unique Benson Bubblers! These decorative water fountains were installed in the early 1900’s by local businessman Simon Benson in hopes of keeping workers out of the saloons during lunchtime.

Portland’s Living Room

Take a tour of some sort to get your bearings. Several 3-4 hour options leave from Pioneer Square or nearby Director’s Square. I recommend both Peak Tours & Transit and Around Portland Tours.

A Benson Bubbler!

2. Visit Powell’s City of Books

A short walk from Pioneer Square is Powell’s City of Books, the largest independent bookstore in the world. Powell’s sells new, used, and hard-to-find books in this shop that occupies a full city block. The Rare Book Room makes for an interesting stop with books dating back as far back as the late 1400s.

3. Eat in Food Cart Parks

Are you hungry for lunch? Stop at one of Portland’s food cart parks. Use this map to find one of special interest (or just nearby) and discover one of the most charming aspects of Portlandia culture. One evening at the Midtown Beer Market, I came across a cart dedicated strictly to our furry friends! Bring! Treats for Dogs was the perfect place to pick up a souvenir for our Dolce. Their peanut butter-filled empanadas were a HUGE hit.

These empanadas were for me, not Dolce. Thanks El Pilon!

4. Traverse Washington Park & The International Rose Test Garden

Nestled in the rugged and beautiful Washington Park, you’ll find the International Rose Test Garden. This is a must-stop if in full bloom. If the roses aren’t in bloom or if you have more time to spend, check out the Japanese Garden nearby. You could easily spend a day wandering this urban oasis and not see all that it has to offer!

Not just roses at the International Rose Test Garden!

5. Discover Pittock Mansion

Pittock Mansion is the incredible French Renaissance-style chateau built by Henry & Georgiana Pittock. Henry Pittock is best known as the publisher of The Oregonian, a newspaper that is still in print today.

Once you enjoy touring the mansion and grounds, be sure to step outside to enjoy the city viewpoint. Beyond the Willamette River, you’ll see eastern Portland and even Mt. Hood on a clear day.

Mt. Hood!⮕

6. Visit Some McMenamin’s Properties

McMenamin’s is a chain of breweries, hotels, and music venues owned by by brothers Mike and Brian McMenamin. They are well-known in Oregon for their many restoration projects. Notable properties include the Baghad Theatre, the Crystal Hotel, and the Kennedy School. The Kennedy School, once a local elementary, is now a 57-room hotel with bars, eateries, a swimming pool and movie theatre. What a fantastically groovy adaptation of this historic place!

The restaurant inside the McMenamin’s Kennedy School Complex

7. Stroll Tom McCall Waterfront Park

This riverside promenade is lovely to explore any time of day but I think it is prettiest in the early morning or near sunset. If you opt for a morning walk, pick up your obligatory Voodoo Donuts and keep an eye out for Mill Ends Park. This 2 foot diameter, 1-tree park is the smallest in the world according to Guinness. NOTE: Many of the people from Portland that I met recommended Blue Star Donuts over Voodoo.

Caught the rainbow! 🌈
The Portland Steamboat

If an evening stroll is more to your liking, I suggest capping off your walk with a stop at the Royal Sonesta Hotel. Check out its warm and inviting lobby or grab a glass of Willamette Valley wine at Finch on Fifth, the attached bar/restaurant. Alternatively, the Library at the Heathman Hotel is a delightful place to unwind. Fans of 50 Shades of Grey may remember the hotel name from its mention in the book.

8. Hike Columbia River Gorge & Multnomah Falls

They say you can’t come to Portland and not experience the Columbia River Gorge & Multnomah Falls. But somehow I did exactly that. Although I had the best of intentions, I just ran out of time. Don’t you make that mistake!

According to legend, Multnomah Falls were formed when a young girl sacrificed herself to the Great Spirit to save her village from a plague. Whether that’s true or not, I don’t know but they sure are beautiful! Marking this as the #1 thing to do on a return trip.

Best Things to do in Portland Oregon

9. Explore Tillamook Creamery

Did I save the best for last? You be the judge! Tillamook Creamery is a scenic, 90-minute drive from downtown Portland but well worth the trip for cheese and ice cream lovers. The factory offers both guided and self-guided where you’ll have the opportunity to see Tillamook employees making their delicious cheese!

You can grab a bite to eat in the dining hall and stock up your fridge with some of the many selections in their large retail area.

Don’t miss the Tillamook Taste Bud Ice Cream Experience! You’ll enjoy more scoops of ice cream than you can dream of and will find out if you have what it takes to be a Tillamook Supertaster.

NOTE: If you are traveling with kids, keep an eye out for these child-height peepholes. Inside you’ll find cute little depictions of cows, etc. There are supposedly six hidden throughout the complex!


I hope you’ve enjoyed these very best things to do in Portland Oregon! More travel content can be found here. Thanks so much for your likes, shares, and follows! Until next time,

Heading to the Pacific Northwest? These are the 9 very best things to do in Portland Oregon! #portlandoregon

Author: Betsy Ramsey

Betsy Ramsey is the author of Natty Gal. Born and raised in Northeast Ohio, she now lives there with her husband and Bichon-Frise, Dolce. A mindful fashion & capsule wardrobe enthusiast, she travels extensively, visiting 56 countries to date. Betsy is committed to helping others live their most fulfilling life!

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Splendid