See the Real Portland

Portland isn't a megacity like NYC, Mexico City, or Seoul where you could easily make a 7-day vacation out of the city alone and be busy each and every day. This means two things:

(1) Taking a peek at Regions of Oregon will serve you well in planning the trip so as to you can think through which part(s) of Oregon truly excites you and decide how much time you'll want to spend inside (if at all) vs. outside of the metro area.

(2) On the days you are sightseeing the city of Portland, there's little need to stress over the route efficiency. What works well for this compact city is to browse the attractions introduced in this post and save the ones you like on Google Maps (or your navigation app of choice). Each day, simply lump together attractions in the vicinity of each other. This is much more meaningful and practical than me guessing and telling you where to go in the morning, where to eat lunch, where to go in the afternoon, etc.

If any transit between sites ends up being a bit too far to walk, Uber/Lyft is affordable, unlike in bigger cities (looking at you, LA) and public transportation like the MAX (light rail) and buses are very well integrated into Google Maps and even more affordable than rideshares.

Famous Attractions

Powell’s City of Books

Famous for being the biggest independent bookstore in the world, Powell's City of Books knocks any big-box bookstore out of the park in several ways. Yes, first off, it's humongous, and my favorite part is how big their used & rare book selections are. It's also fun how the staff leaves hand-written notes on their personal recommended books and how different categories of books are organized in color-coded rooms.

Powell's City of Books

Food Carts

Clusters of street food carts (pods) make for iconic cultural scenes of Oregon, with Hawthorne Asylum, Hinterland, and Prost! being some of the well-known ones in Portland for diverse and high-quality offerings. Sure Oregon has many food carts and coffee carts, but I also want to emphasize the pods are more than just street food. Not only are they a form of cozy little communities, they also represent the people's passion for economic accessibility and creative freedom. Unlike in most other parts of the world where breaking into the food or drink industry requires huge capital (a.k.a. debt), Oregon's aspiring chefs can start small with relatively low investment into a food cart. If you’ve got talent and a fresh culinary idea, your cart can easily take off, eventually letting you graduate to a full-fledged restaurant. The norm for many other cities might be opening a traditional restaurant first, then serving with pop-up carts once the restaurant gained its name value. Here, a humble food cart often serves as the original hub, while the owner's sleek new restaurant is often a byproduct - a charming "reverse career path" so to speak.

Washington Park

West of the city center, another great attraction is Washington Park. You can drive there, but can also utilize the MAX (light rail), especially since free shuttles run between the MAX station and the park. This place is really a collection of multiple visit-worthy spots, so refer to this post dedicated for Washington Park! In short though, Hoyt Arboretum offers various walking trails to relax and admire the pines and redwoods. The International Rose Test Garden won't disappoint if you are here in mid-Summer when it will be bursting with countless rows of colorful roses. The Portland Japanese Garden isn't free but can be worth it if you are into Japanese style gardens or they are hosting an event of your interest.

A peaceful misty trail at Hoyt Arboretum

Pittock Mansion

This is a particularly attractive destination on a clear day. Inside the mansion are furniture, art, and artifacts from the early 20th century when Portland was rapidly evolving into a modern city (ticket required.) But the real treat in my opinion is the outdoor area surrounding the mansion, which is free to stroll about. The panorama of Portland downtown with Mt. Hood as its backdrop is quite a spectacle. If you aren't feeling like walking up the hill there is a parking lot right by the mansion. But if you are hoping to combine the visit with some exercise, Wildwood Trail leads right to the mansion. This hike is introduced in detail below in the City Hikes section of this post.

Portland Art Museum (PAM)

If you're an art lover, punching in 'art gallery' in Google Maps will get you a great collection of small independent galleries scattered all over the city, free to browse. But if you prefer seeing a variety of works all in one place, or if the weather is blah, Portland Art Museum (PAM) is a nice alternative. Heads up though, parking options aren't good around here, so it’s better to take an Uber or Lyft. This is also one of those streets where the vibe changes drastically from one block to the next. One direction might lead you to a well-kept clean park, and then just a couple blocks in the other direction there may suddenly be a group of unhoused people. So honestly, I wouldn’t suggest walking to PAM.

Guided Tours

Viator has a lot of Portland walking tours listed, and you can't go wrong picking whichever one has a high rating and good recent reviews. Options range from classic sightseeing tours that give a general overview of the city's attractions, culture and history, to more niche experiences like underground tunnel tours, beer tasting walks, coffee & donut samplings, and even e-bike or aircraft tours. Try exploring to find something that suits your taste. 

✧Local's Tip✧

One spot in Portland that often disappoints tourists is Voodoo Doughnut. It’s located on a rundown street with a large unhoused population, so the vibe is eh. Their donuts don’t live up to the hype either, at least to my personal taste. (Blue Star Donuts is better.) But if you still feel like you’ve got to try the Voodoo at least once, which is completely fair, I would skip their main store and head to the east side branch.

Speaking of disappointing tourists, Stumptown Coffee... doesn’t quite live up to its reputation either. Of course it depends on your preference of bean type, roasting style, etc., and their rich history is something not to be ignored. But the PNW has developed such a rich coffee culture that you'll find smaller, lesser-known roasters with higher quality coffee everywhere. Really, just search “coffee roasters” near your location on Google Maps, and look for places with high ratings and recent good reviews. They will be matched or better than Stumptown in taste.

Normally I avoid putting too much food and drink talks in my posts, to keep the focus rather on things to see and do, but I felt this city-centered post warranted a bit more blabbering about the culinary fare.

Less Famous Attractions

Aerial tram

Portland's aerial tram is a great way to relax while enjoying the green city view from higher up. Day time rides with a bright view and evening rides with their golden sunsets both have their merits. Check out their seasonal operating schedule at http://www.gobytram.com/ - you can purchase the ticket either in advance online or same day on site at the terminal.

River Cruise

Portland Spirit offers a range of cruise types at different times of the day—some will be eating- or drinking-focused, while some will be more focused on admiring scenery. Choose wisely (kidding, no bad option here) and treat yo’self. River breeze can be chillier than expected, so packing a light jacket is usually a smart move.

Urban Wine Tasting

If you're a wine lover but don't have time for traditional winery visits to Willamette Valley or the Hood River region, urban tastings are a great alternative. It's as simply as ‘urban winery’ on Google Maps to find a top-rated spot close to your accommodation. If you'd prefer to plan your visit with a bit more research, Portland's Urban Wine website has a great up-to-date list of wineries to help you pick your favorite.

Korean snacks, anyone?

Not a sightseeing spot, obviously, but H Mart Belmont has a great selection of Korean munchies (snacks, sweets, drinks, and even quick groceries like ramen if your lodging happens to have a kitchenette) to accompany the rest of your travel. Can't go wrong with Turtle Chips.

City Hikes

You might've noticed flying into PDX - Portland’s got nature woven right into the city. The urban greenery makes it possible to enjoy a wide range of hikes without leaving town, and here are a few trail suggestions near and dear to the locals.

Pittock Mansion 

The mansion sits atop the west hills of Portland, so the trail includes a bit of elevation gain (890 ft). But as long as you take it easy and bring enough water, it’s totally doable for folks with average fitness. (Round-trip is about 5 miles.) The trailhead I recommend is Lower Macleay Park, but if parking's tight there—or if you want to shorten the walk to around 2.5 miles—you can start here instead.

◑ in the top right corner marks the Lower Macleay Park trailhead. Credit: alltrails.com

Pittock Mansion

Hoyt Arboretum 

Hoyt Arboretum's layout is more like an open forest with interwoven trails than a manicured garden with a singular walking path. You can meander about with no plan or with a rough plan using the trail map.

If you’ve brought a car, I do recommend parking along Fairview Blvd because if you find a spot without a meter here, it’s free street parking!😉 From there, I like to stroll west on Redwood Trail, which connects to Wildwood Trail, then head east to catch the views from Overlook Trail.

Washington Park’s shuttle makes it super accessible without a car as well. If you hopped off the shuttle at the arboretum visitor center, I would start by crossing the street from the Visitor Center to the southern end of the Redwood Trail.

That said, Hoyt Arboretum has such great variety of trails, each with its own charm, you can just let your instincts pick the path for you. The route I introduced above is simply one example that I personally find enjoyable.

Forest Park

If you’re looking for an even quieter trail, further removed from the bustles of the city, head by car to the northern area of Forest Park. The most well-known main trail—Wildwood Trail—runs north-south and even passes by Pittock Mansion at its southern end, but there are tons of offshoot trails branching from Wildwood for you to pick and choose. Take a look at the trail map and choose one that matches your interest and fitness level. I personally enjoy lack of people on the trails that connect off of Firelane 5 and Firelane 10, FYI.