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14 Things to Do In Portland

With the motto “keep Portland weird,” Portland is one of the most well-known and eccentric cities in the United States. It is renowned for having vast swaths of greenery, from parks and forests to magnificent mountaintops. You can find both cool and weird things to do that will make your stay worthwhile in this city, where weird is cool, craft beer is mainstream, and nature is interwoven throughout the city. These include strolling through Chinese and Japanese gardens, participating in a naked bike ride, and visiting historical monuments. So, in this video, we’ll go through 14 things you absolutely must do when visiting the Rose City.

Table of Contents

Stroll through the Japanese Garden and the Rose Test Garden

Both located at Washington Park, the Japanese garden is regarded as the most authentic outside of Japan, and the Rose test garden is the oldest of its kind in the United States. The rose garden houses over 610 varieties of roses, and helps give Portland its nickname, “City of Roses”. The 12 acre neighboring Japanese garden features 8 different garden styles, including a Japanese Tea House. Once you are done with the gardens, Washington Park is home to many more attractions, like the Oregon Zoo, Hoyt Arboretum, and breathtaking views of downtown Portland and Mt. Hood.

Tour Pittock Mansion

Pittock Mansion, once home to Portland’s original power couple Henry and Georgiana Pittock, is one of the city’s few historical must-see attractions. The mansion, which is located along the Wildwood Trail south of Forest Park, was built in 1914 in the striking French Renaissance style. It covers approximately 16,000 square feet, has 46 elaborate rooms, and is open to the public. The house was built so well that the original elevator still works today. A tour of the mansion is a must-do in Portland, and it’s also one of the best places to get panoramic views of the city.

Pay a visit to the Lan Su Chinese Garden

The Lan Su Garden, known as the most authentic Chinese garden outside of China, personifies serenity and tranquillity. This walled garden will instantly transport you from the United States to China. The 40,000-square-foot garden was built in 2000 to connect locals with Chinese culture. Designed by Suzhou artisans in the Ming Dynasty style, its covered walkways, bridges, open colonnades, koi-filled ponds, pavilions, and richly planted landscape framing the man-made Zither Lake have created an urban oasis of tranquil beauty and harmony. You won’t want to miss the garden if you want to learn about and experience Chinese culture without leaving the States.

Hike the Columbia River Gorge

The Columbia River Gorge, located just 25 miles east of Portland, allows you to immerse yourself completely in nature. It has waterfalls, scenic vistas, and hiking trails, so if you want to get away from Portland, this is the place to go. It is the country’s largest National Scenic Area and a pleasant place to spend the day. Multnomah Falls, Oregon’s tallest waterfall, is located here, as is a century-old observatory with views of the surrounding picturesque landscape. Visiting this beautiful region is well worth the trip and will be an excellent addition to your time in Portland.

Hike to the Witch’s Castle

A ruined stone house covered in moss and shrouded in mystery lies along a hiking trail in the middle of the forest: the Witch’s Castle. It is one of the strangest places in a city that celebrates the strange. The Witch’s Castle, despite its name, has nothing to do with witches. In fact, the two-story structure is officially known as the Stone House. High Scholars who began holding kegger parties there in the 1980s dubbed it the Witch’s Castle. However, the ruins have a long history of tragedy dating back to the 1800s. Hiking to the Witch’s Castle feels like a rite of passage in Portland, so don’t miss it if you’re there.

Take a photo with the Portland motto sign

“Keep Portland Weird” is a popular slogan that can be found on bumper stickers, signs, and public buildings throughout the city of Portland. It was introduced in 2003 as part of a campaign to support local businesses. No sticker, however, rivals the massive painted wall located just south of the Burnside bridge. Posing and taking photos beneath the sticker is an iconic Portland activity! So don’t skip it during your visit.

Ride the iconic Portland Aerial Tram

Portland Aerial Tram, one of the country’s only aerial commuter trams, connects South Waterfront to Marquam Hill. The tram was built to alleviate traffic congestion on the main road leading to campus. One of the things to do in Portland is ride the tram. The 4-minute ride ascends 3,300 feet at a speed of 22 mph, rising 500 feet above the ground. It’s not only entertaining, but it also provides breathtaking views of the city from above.

Eat from a food cart

Food trucks, also known as food carts in Portland, thrive in the city’s culinary scene. Portland’s food-cart scene is legendary, with hundreds spread throughout the city. Portland, with its abundance of fresh and local ingredients, is a city where street food can compete with the best restaurants. And, unlike other cities’ mobile food trucks, most Portland carts stay in groups known as “pods,” making it easy to try several at once. So you can sample international flavors and new food concepts without having to wait in line at a traditional restaurant.

Take a hike in Forest Park

Forest Park is a must-see for natural escapes in the midst of Portland’s urban setting. This Pacific Northwest forest’s dense, lush expanse spans 5,200 acres, making it one of America’s largest urban green spaces. It’s also one of the city’s free things to do, with no entrance fee, and is ideal for sightseeing and relaxation. It’s the perfect place to get away from the hustle and bustle of city life, with over 70 miles of trails crisscrossing the park, including the popular Wildwood Trail, which is part of Portland’s 40-Mile Loop. There are also over 100 bird species and 62 mammal species. The already mentioned Witch’s Castle is also located in the park.

Explore the Pearl District

The Pearl District is a trendy Portland neighborhood full of art galleries, independent stores, fashion boutiques, and fine dining options. If you’re looking to indulge in some retail therapy while in Portland, this is the place to be. The Pearl, once an abandoned warehouse district, has been revitalized as a model urban center, serving the needs of its residents while also attracting tourists. There is plenty to keep you occupied, from browsing the vibrant big brand shops to exploring the many art galleries and treating yourself to a fresh coffee or a bite to eat at one of the highly rated bars or restaurants.

Visit Powell's city of Books

Powell’s City of Books is worth a visit whether or not you are a reader. Powell’s City of Books is the world’s largest used and new bookstore, taking up an entire city block and housing approximately one million books spread across 3,500 sections, three floors, and nine color-coded individual rooms. The structure is so large that it has its own map, which you can obtain at the front desk and use to navigate through sections for every topic and genre imaginable. Throughout the year, many famous writers visit the store, each leaving their mark in the form of a signature on one of the pillars inside. It is a must-see attraction that you should not miss.

Attend the Naked bike ride

Imagine hundreds, if not thousands, of naked people cycling through the city! That’s what happens every year in Portland during the World Naked Bike Ride. This annual event has seen Portlanders pedaling au naturel every June or July since 2004, as part of a worldwide protest against oil dependency. It’s definitely one of the oddest things to do in Portland. If you feel up to it, you can join the riders or simply cheer them on from the sidelines.

Visit The Freakybuttrue Peculiarium

The Freakybuttrue Peculiarium, founded in 1967 by Oregon native Conrad Talmadge Elwood, an explorer who loved the bizarre, weird, and zany, keeps the spirit of the Keep Portland Weird slogan alive. If you’re looking for something out of the ordinary to do in Portland, this is one of your best options. Shelves in The Freakybuttrue Peculiarium’s gift shop are crammed with cheap gag toys, strange pop artifacts, unsettling specimens, and more, all positioned behind the massive statue of Bigfoot that greets you as you walk in.

Relax in Portland’s Living Room at Pioneer Courthouse Square

Pioneer Courthouse Square, also known as Portland’s living room, is a great place to start when exploring this wonderful city. Since its inception in 1984, it has served as a meeting place for both visitors and locals in the heart of Portland’s downtown. It is a common event space with 40,000 square feet and a plethora of fascinating features to look at. Pioneer Courthouse Square features a fountain that resembles a waterfall, a chess table, and the much-loved Umbrella Man, a bronze statue of a man in a suit carrying an umbrella.

Things To Do Video

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