Portland is known from the outside for its friendly people, great food scene, and ability to raise chickens in your own backyard. These are all true. But there is so much more to Portland’s daily life that attracts both locals and visitors.
Yes, the amount of unique things you can do in Portland, Oregon is seemingly endless.
Visitors have been flocking to the city in large numbers over the years, eager to experience the excitement. Time is limited, so there is no need to waste it on tourist traps and mediocre restaurants – especially in Portland.
I’m a Portland Realtor and I have lived here all my life. I love the uniqueness of my city, so I’ve decided to share my personal list with you of the top things to do in Portland.
The 12 best things to do in Portland
These are not in any particular order and are simply my opinions. There are many fun and unique things to do in Portland, and everyone will find their own favorites. This is my list of the top things to do in Portland.
1. The Portland Japanese Garden offers zen and tranquility
The Portland Japanese Garden was established in 1967 and is widely regarded as one the most authentic Japanese gardens in America. You’ll see why when you go. The garden has a few waterfalls, a small pond and paths that are moss-laden.
The garden is a great place to escape from the city for a bit to just sit and relax. You can order matcha at the Umami Cafe or any of the other teas on the menu. You won’t regret it.
This experience is a must-see for anyone visiting Portland for the first time. It’s especially great if you visit in the fall when the garden really comes to life!
2. Explore the Pearl District
Portland’s Pearl District can best be described as industrial chic. The beautiful red brick buildings have been surrounded by towering high rises. These two worlds seem to merge seamlessly.
The Pearl District is well-known for its many independent boutiques, cafes, bars, and charming galleries, making it one of the most popular Portland neighborhoods. The Pearl was once home to factories and loading docks. It has since been redesigned and is ready to display its new look.
Since then, the warehouses have been transformed into light-filled condos. The cobblestone streets of the past continue to lead the neighborhood into the future. The Pearl District is a living testament to the power that bringing new life back into an area can have.
3. Shop at the largest bookstore in the world
CNN rated Powell’s Books as one of the coolest bookstores in the world. Also known as City of Books, Powell’s Books is the largest independent bookstore in the world. They sell both new and used titles.
Powell’s Books is located in the Pearl District and covers an entire city block.
The store is home to over 1 million New and Used Books. It covers four floors. Before you embark on your adventure, make sure to grab a map. Be prepared for crowds unless you arrive early. Powell’s is definitely one of the best things to do in Portland.
You can visit the Gold Room to view the rarest books available. The most expensive Powell’s book is a 1814 copy of the Lewis and Clark Journal. This journal includes Captain Lewis’s map, which is safely hidden between the pages. What is the price? $350,000!
4. Stroll down Mississippi Avenue
When people think of Portland’s quirkiness, they often think about Mississippi Avenue. This is why exploring this area is one of the best things to do in Portland.
Mississippi Avenue is filled with vibrant storefronts and local shops that cater for every millennial’s whim. You’ll find a wonderful plant nursery, great restaurants, food carts and breweries as well as charming shops.
Mississippi Studios is a great place to see live music. You can check it out and grab tickets for a show.
5. Visit Pittock Mansion
Pittock Mansion, according to history buffs, is one of the most exciting things to do in Portland.
Pittock Mansion, a magnificent French Renaissance mansion, is located atop The West Hills. It spans 16,000 square feet and boasts 46 rooms. The house is also open to the public. It was so well built that the original elevator still works today.
These tours are great because you can see original furniture from that time and learn more about the family who built it.
The Mansion’s Christmas decorations are extraordinary, with tons and tons of Christmas trees.
If time is tight and you can’t make it to the Mansion, at least head to the lookout behind it for stunning views of downtown Portland.
6. Enjoy Tom McCall Waterfront Park
The Tom McCall Waterfront Park was named for Oregon’s most revered governor. It’s common to see locals at the park during lunch hours. You’ll likely be avoiding bikers, walkers, and skateboarders as well as young couples walking hand-in-hand.
This is a popular stop for families with children, as it’s right on the Oregon Maritime Museum’s waterfront. If you are looking for something to do in Portland on Saturdays, stop by the Portland Saturday Market. Local merchants sell unique products. This is a great place for souvenirs.
In 1990, the Japanese Grain Importers Association gifted 100 Akebono cherry blossoms that line the waterfront. You should plan your trip to the waterfront during the spring season to enjoy the cherry blossoms.
7. Learn about the haunting past of the Witch’s Castle
You may be wondering what is so disturbing about an abandoned structure in the middle of a forest. At the heart of this place are two stories: the story about an angry father who is accused of murder and a love-stricken daughter.
This age-old tale about haunt and murder makes a visit at The Witches Castle even more fascinating.
Portlanders will tell you that hiking up to the witch’s castle feels like an rite of passage. It feels just as part of Portland as the Keep Portland Weird slogan, so you can’t miss it when you visit. It is also a fun hike.
8. The smallest park in the world
The Guinness Book of World Records in 1971 confirmed what most portlanders knew: Mills End Park is the world’s smallest park. Mill ends Park, measuring just 2 square feet, is officially the smallest park in the world.
This little Park is a treasure and one of the quirkiest things to do in Portland. This is a short stopover that can be combined with other interesting things in Portland. The park is a great opportunity for a fun Instagram post.
9. Order takeout from a food cart
Portland is a city that’s known for its foodie culture. Portland’s food cart scene is my favorite part. It lacks pretension. You can have a delicious meal without having to go to a fancy restaurant.
This is most apparent with the food cart pods scattered throughout the city.
Food trucks are not just for tourists. My coworkers often eat lunch at food trucks, so it’s more local than touristy.
Here are some popular Portland food cart pods.
- Hawthorne Asylum
- 5th Avenue pod
- 3rd Avenue pod
- Cartlandia
- Cartopia
- Prost Marketplace
10. Do a wine tasting at The Portland Wine Company
Imagine spending a summer evening with friends and enjoying a wine tasting at a wine bar. If this sounds like fun, then The Portland Wine Company might be the right place for you.
The Portland Wine Company, Home of Love & Squalor Wine (and Jackalope Wine), is an urban wine bar, a wine-tasting room, and a wine store that is located in Downtown Portland, Oregon. They specialize in the best local handcrafted, small-batch wines from the Pacific Northwest (PNW).
Portland is home to many great wineries and wine bars and they are making a big impact in the city not only because they are convenient but also because they have access to a variety of grapes that can be harvested and bottled.
11. Enjoy Cathedral Park Jazz Festival
If you are looking for something fun to do in Portland in the summer, I recommend that you attend the annual Cathedral Park Jazz Festival. It is held over the course of a long weekend and is a great place to start your summer.
The Festival is open for all ages. It brings together jazz lovers in an informal setting. You can bring a blanket or a camping chair and enjoy the pure bliss of music.
Cathedral Park Jazz Festival is a great free thing to do in Portland in the summer.
12. Enjoy a walk in one of the most extensive urban forests in the country
Forest Park in Portland, Oregon is an urban forest that covers more than 5,200 acres. It offers 70+ blissful miles of trails and is open for exploration.
Forest Park is a great place to go for an active day in Portland.
Due to the plentiful large trees, the park swallows you up, making you forget you are anywhere near a city.
I love small sections of the Wildwood Trail, the Ridge Trail, and the lower mackley to Stonehouse, Witch’s Castle.
Summary of things to do in Portland
As you can see, there truly are many great and unique things to do in Portland. And this list is just the tip of the iceberg. The Portland theater scene is also popular among locals. There are plenty of other resources online with a seemingly endless list. I hope you enjoyed my personal favorites.
Here is a quick list of my favorite things to do in Portland, Oregon in case you want to take a screenshot to reference later.
- The Portland Japanese Garden
- Explore the Pearl District
- Shop at the largest bookstore in the world
- Stroll down Mississippi Avenue
- Visit Pittock Mansion
- Enjoy Tom McCall Waterfront Park
- Hike up to the Witch’s Castle
- Visit the smallest park in the world
- Order takeout from a food cart
- Do a wine tasting at The Portland Wine Company
- Enjoy Cathedral Park Jazz Festival
- Take a walk in Forest Park