The Ultimate 3-Days in Portland, Oregon

Pittock Mansion

If you’re visiting the Pacific Northwest, Portland should definitely be on your list of places to see. It’s a unique city with delicious food and friendly locals who embrace the motto “Keep Portland Weird.” With a mix of city and outdoor activities, there will be something for everyone to enjoy. Here is a list of everything you should do and eat during your three days in Portland, Oregon!

Day 1

Start your day off with a hearty breakfast. Fried Egg I’m In Love has Portland’s best breakfast sandwiches. Each sandwich has a cute punny name and a perfectly cooked egg. There are three locations – two food carts and one restaurant. The cart in Pioneer Courthouse Square is closest to our next stop, Pittock Mansion.

Pittock Mansion

In the 1800s, the Pittock Family was one of the most influential families in Portland. Constructed in 1914, Pittock Mansion was their private home until 1958. After some rehab, it opened to the public in 1965 and has become a city landmark. There is a fee to tour the house, but 100% goes to preserving the mansion.

If you’re not interested in seeing the mansion, I’d still recommend coming by for the viewpoint. It’s free to stop by, and you’ll get a fantastic view of the Portland skyline. On a clear day, you can see Mt Hood, Mt St Helens, and Mt Rainier. 

Washington Park

Just a short drive from Pittock Mansion is Washington Park. The park features the Oregon Zoo, Hoyt Arboretum, and multiple museums. 

The Portland Japanese Garden is also located in Washington Park. The garden covers 12 acres with koi ponds, bonsai trees, and a rock garden. It’s a great way to learn about Japanese culture with the Cultural Village, Japanese Tea House, and art exhibitions.

A short walk from the Japanese Garden is the Portland International Rose Test Garden. The garden offers free admission and features more than 10,000 roses representing 600 varieties. 

Portland Oregon White Stag Sign

Food Carts

Before visiting Portland, I wasn’t sure there was a difference between a food truck and a food cart. Since then, I’ve learned that in Portland, the carts stay put in “pods” versus a food truck that moves from place to place. Portland takes its food carts pretty seriously. There are more than 500 carts in the city where you can get everything from sushi to BBQ.

One of our favorite meals in Portland was at Stretch the Noodle, part of the Third Avenue Food Cart Pod. They offer noodle soup, stir-fried noodles, and noodle salad. No matter what you order, the noodles are hand-pulled. The pod also has carts with Mediterranean, American, and Mexican cuisine.

After you get your food, you’ll notice there aren’t many places to sit and eat. TomMcCall Waterfront Park is a few blocks away and has benches where you can enjoy lunch along the Willamette River. If you are here during the spring, this is one of the best spots in the city for cherry blossoms.   

Voodoo Doughnut

If you still have room for dessert, grab a doughnut from Voodoo Doughnut. The Old Town location is the original shop that started it all. 

If you’ve never heard of it, Voodoo Doughnuts is known for its fun, colorful, and occasionally NSFW treats. While they have traditional glazed and cinnamon sugar, there’s also the “old dirty bastard” and “maple blazer blunt.” The bakeshop definitely reinforces Portland’s reputation as a “weird” place.

Lan Su Chinese Garden

Lan Su Chinese Garden in Portland

Nestled right in the middle of the city, you’ll find Lan Su Chinese Garden. While I’ve never been to China, Jack has, and he confirmed that many of the gardens there are just like this. Lan Su takes up a whole city block and features over 400 species of plants. You can choose to explore on your own or take a free tour. There’s also a small teahouse with snacks and tea.

Day 2

Keep Portland Weird sign

Another highly recommend breakfast spot in Portland is Pine State Biscuits. They have the perfect flaky, homemade biscuits you can get as a sandwich or covered in gravy. 

Northwest 23rd Avenue

I love an area where you can walk around to explore, and Northwest 23rd Avenue is just that. The street is lined with shopping, restaurants, and cafes. There are familiar retailers, like Urban Outfitters and Lush, but I would also check out the local shops, like Budd + Finn, for a cute souvenir. 

While walking in the neighborhood, you’ll likely see a long line outside an ice cream shop, even in the winter. This is Salt and Straw. The shop is known for its handmade ice cream and unique flavors. While they have the usual vanilla and chocolate, they also have scoops with black pepper and olive oil.

Powell’s City of Books

Powell’s City of Books covers a whole block making it the world’s largest new and used bookstore. It’s so big that they have a map you can grab at the info desk to help you navigate through the store.

Stumptown Coffee Roasters

Stumptown Coffee storefront

Stumptown Coffee is probably the most well-known coffee shop in Portland. They first opened in 1999 and have since expanded with cafes in LA, New York, and even Japan. You might recognize the name as it’s now available in grocery stores nationwide.

Portland Aerial Tram

While driving around town, you might notice a cable car traveling above you. This is the Portland Aerial Tram, one of the few commuter aerial trams in the country. It was built to connect the Oregon Health & Science University’s campus to the South Waterfront district. 

To be honest, it’s a pretty short ride (four minutes each way), and there will likely be more people on the tram who are actually visiting the University rather than sightseers. However, I think it’s worth a stop as you get some beautiful panoramas of the city, the waterfront, and Mt Hood.

View of Portland and Mt Hood


Did you know that Portland is considered one of the best beer cities in the U.S.? While IPAs are a Portland staple, you can find a brewery for just about any type of beer. You can always visit the breweries on your own, or if you want to make the most of your time, you can also do a beer tour by bike, party bike, or bus.

Day 3

For your last day in Portland, I’d recommend trying something besides the usual American breakfast. Jianbing is a traditional Chinese street food that is very popular for breakfast. It’s made up of a savory crepe filled with egg, chili sauce, herbs, and crackers. Sooo good! In Portland, there’s no better place to get one than Bing Me Food Cart in the Nob Hill Food Cart pod. 

A trip to Portland wouldn’t be complete without some time spent in nature. The Columbia River Gorge is the biggest National Scenic Area in the U.S. and stretches between Oregon and Washington. The canyon runs over 80 miles and is one of the best places for hiking and sightseeing, with more than 90 waterfalls. 

Crown Point Vista House

Crown Point Vista House

The Crown Point Vista House is one of the best stops to get some epic sights of the Columbia River Gorge. It’s a free observatory, rest stop, and museum (with a gift shop). While it’s easy to get distracted by the sweeping views of the canyon, take a minute to check out the Vista House itself. The building’s interior is made mainly of marble and limestone, with opalized glass windows in the rotunda. 

Latourell Falls

Latourell Falls is the closest waterfall to Portland and has a lower and upper section. A short walk from the parking lot is the lower falls. It stands at over 200 feet and is perfect for those who aren’t really looking to do any hiking. If you want to reach the upper falls, it’s a 2-mile moderate hike.

Bridal Veil Falls

A short distance away from Latourell is Bridal Veil Falls. The lower trail is short but steep and will take you to the waterfall’s base, where there’s a viewing platform. The upper trail is the Overlook Trail (about ½ mile loop) and will give you views of the Columbia River and surrounding mountains.

Multnomah Falls

Multnomah Falls is Oregon’s most famous waterfall, and it’s easy to see why. It’s the tallest waterfall in the state and the bridge that spans the falls, Benson Bridge, is a unique feature. Expect it to be busy year-round, especially during the summer.

A viewing platform at the base of the falls gives you the best view of both cascades and the bridge. Take the short trail to Benson Bridge to get an even closer look. Multnomah Falls is accessible year-round but does freeze over in the winter. For more of a challenge, there’s a 2.5-mile hike to the top of the waterfall. 


A weekend in Portland is a great way to see how the city has developed its reputation as one of the most hipster places in the U.S. This guide covers just a few of the quirky spots and scenic hiking trails that have made Portland so popular. 

Leave a Comment