13 ways to see the best of Portland, Oregon

Portland is a city that embraces its wild side. From the farm-to-table abundance of its restaurants and markets to the forested trails that thread through its distinct neighborhoods, dramatic landscapes and natural treasures show up in all aspects of life here. And to fully appreciate how it all ties together in this city of roses and bridges, you have to spend time both indoors and out. 

Luckily, in Portland, it’s easy to switch between the two. You can go hiking in Forest Park, then sit down at a James Beard Award-winning restaurant. You can lounge on a beach or sip an artfully crafted latte at a cozy cafe. Yes, it does rain for much of the year here. Yet even on the worst weather days, Portland will beckon you outside with its lush forests and gardens, then warm you up with its coffee, food, beer and uniquely Pacific Northwest experiences. 

Here are 13 of the best ones.

1. Walk or bike the bridges 

In Portland, 12 bridges span the width of the Willamette River – hence the nickname “Bridge City.” For a nice long walk or a breezy bike ride, count on crossing the river a few times for an introduction to the city. From the Burnside Bridge, you’ll spot Portland’s iconic white stag sign. A loop from the Burnside Bridge to the Tilikum Crossing Bridge – Portland’s newest river crossing and the only one that does not allow cars – will cover about 4 miles. For a 2-mile walk, start at the Hawthorne Bridge. Either way, you’ll pass Poet’s Beach and the Oregon Rail Heritage Center. 

2. Hike to the Witch’s Castle 

With over 80 miles of trails, Forest Park is one of the largest urban parks in the country, and it can be hard to decide which section to explore. Lower Macleay is a popular place to start – and for good reason: the trail is a gentle, mossy meander through an exquisitely green section of the park. You’ll follow the course of Balch Creek, with a handful of access points where you can dip your feet on hot days. Just under a mile into the forest, you’ll come to the Stone House, better known locally as the Witch’s Castle. While there’s no verified connection to witches here, the stone structure is a cool piece of architecture in the woods and a nice place to stop for a rest on a hike. 

Detour: From the Stone House, you can continue straight onto the Wildwood Trail for a challenging, 6-mile round-trip hike to Pittock Mansion, the home of an early Portland settler. On a clear day, you’ll catch one of the best views of the city, with Mt Hood looming over the skyline. 

3. Unearth treasures at Hawthorne Ave’s thrift shops 

Portland fashion is eclectic, casual and very often thrifted. It’s a reflection of the city’s quirkiness as well as a commitment to sustainability – for who needs fast fashion when you’ve got treasure troves of style, passed down through the generations? 

Hawthorne Ave in Southeast Portland is home to a high density of thrift stores, where you can shop all afternoon with plenty of breaks for food and beverages. Start at House of Vintage – and get ready to search for treasures in multiple rooms of overflowing racks that run the gamut on quality and styles. Red Light Clothing Exchange is extra quirky, with a lot of affordable, costumey pieces. 

4. Try all the donuts – and pick your favorite 

Voodoo’s pink boxes are ubiquitous among tourist crowds, but most locals will urge you to branch out and find your own favorite. I’d recommend starting with Blue Star’s signature Cointreau Crème Brûlée, with its rich vanilla custard and pipette of orange liquor pressed into a torch-fired candy shell. Or grab half a dozen of freshly fried mini donuts topped with cinnamon sugar and Nutella from Pip’s Original. 

Local tip: If you’re visiting on your birthday, Pip’s will give you a free dozen – a perk that’s a testament to Pip’s embrace of community and good vibes. While you’re there, don’t skip the flight of unique chai lattes. 

5. Bring a picnic to Mt Tabor 

This city peak is a popular workout spot, with runners and walkers ascending the many sets of stairs. You can also take it easy and bring a picnic to this extinct volcano, with sweeping views of the city at the top. On nice days, people bring picnic blankets to the west side of the peak to enjoy the sunshine and views – a wonderful free activity in a sometimes pricey town. 

Detour: The so-called Barmuda Triangle is an unofficial collection of grungy dive bars on Hawthorne Ave, at Mt Tabor’s base. Space Room Lounge is a cavern of a watering hole with celestial paintings and velvet artwork that glows in the otherwise dark space; there’s also a big, sunny patio. Other dives in the mix include Bar of the Gods, The Trough and Zach’s Shack (where you can get hot dogs with your beer). Bar-hop around here for a taste of old-school, no-frills Portland.

6. Admire unique blooms at the International Rose Test Garden 

Roses start blooming all over the city in late spring – and to fully immerse yourself in the rainbow of colors and varieties of the city’s favorite flower, you’ll want to head to the International Rose Test Garden in Washington Park. Featuring over 10,000 rose bushes, the park acquired its international standing as a test garden when hybridists from Europe started sending the bushes here during the First World War to preserve them. Today, it remains a testing ground for new varieties and a showcase of some of the most stunning roses in the world. 

7. Learn about the state’s past at the Oregon Historical Society  

At this far-reaching history museum, you can learn about the geography, people and events that shaped Oregon. “Rivers, Roses and Rip City,” the newest permanent exhibit, covers how Oregon’s communities and activism have shaped city spaces. The museum is free to city residents and $14 for visitors. 

Local tip: Visit the museum on a Saturday, and you can also grab lunch at the PSU Farmers Market, where you’ll find over 100 vendors selling all kinds of local food.

8. Buy a bunch of books at Powell’s 

It’s easy to get lost in this city-block-size emporium of literature. And that’s half the fun. Powell’s is a centerpiece of Portland’s literary scene, and perusing its stacks of new and used books is a perfectly Portland way to spend an afternoon. Staff recommendations and themed end-cap displays make it easy to discover something unexpected. 

Local tip: Grab a few titles before you head to one of Portland’s many coffee shops. You won’t have to go far: Guilder, a local roaster, has a cafe on site. 

9. Discover a family-friendly farm experience 15 miles from Downtown 

Chickens and children are all free-ranging at Topaz Farms, a sustainable and beloved family farm on Sauvie Island, just outside the city limits. It’s a great place for families: parents can enjoy local beers while kids eat hot dogs between visiting the goats and the pigs. It’s also just a delightful place to spend a day for all ages. In the summer months, come for the evening concerts featuring country, folk or bluegrass. 

Local tip: Entrance to Topaz Farms is free unless there is a special event or it’s a weekend in October, when the Fall Harvest Festival attracts big crowds. On October weekends, you’ll have to reserve tickets in advance to enjoy the hay rides and pick-your-own-pumpkin field. 

10. Catch a soccer match 

In Portland, as in Europe, football means soccer – and catching a Timbers (men’s) or a Thorns (women’s) game is a thrilling taste of the passion this city pours into its professional teams. Games take place at Providence Park in the Goose Hollow neighborhood, not far from the heart of Downtown. You can walk to the stadium from Powell’s, the PSU Farmers Market and the Alphabet District, where you’ll find lots of bars, restaurants and coffee shops to enjoy before or after a game. 

Detour: Kell’s Irish Pub is a lively place to celebrate a win (or nurse a loss) after a big game. The classic pub food pairs perfectly with a cold one with your new fan-friends. 

11. Enjoy a movie and local brews at the Hollywood Theater 

The Hollywood Theater is a temple for film nerds and a dazzling place for anyone to catch a movie. Built in 1926, the space served as both a vaudeville house and a movie theater with an organ and eight-piece orchestra. Today, special programming attracts casual moviegoers and film buffs for rare screenings, new releases and plenty of unique programming (think B-Movie Bingo and the Portland EcoFilm Festival). 

Local tip: Get to the theater a little extra early to enjoy slices of local pizza from Sizzle Pie and some Portland beer. 

12. Eat your way through a “food truck pod” 

Portland was on to the pleasures of food trucks long before they became a national trend – and the city is still home to hundreds of them. A “food truck pod” is a semi-permanent gathering of multiple food trucks where you can find lots of options, plus seating to digest it all. This is a great option for traveling groups: send each person to a different truck in the pod, and you can try a little of everything. A few popular food truck pods include Hawthorne Asylum Food Truck Pod and Cartlandia, both in Southeast Portland.

13. Sip coffee and then beer at a former gas station 

The Cully neighborhood is a mostly residential area in Southeast Portland not far from the airport – and one corner of the district has attracted crowds of visitors and a steady base of neighborhood regulars since opening in 2023. A former garage and gas station is now home to both Junior’s Coffee and Upright Brewing, along with a big asphalt patio with a handful of food carts, including Pine State Biscuits, whose gravy-drenched breakfast sandwiches are a city favorite. The coffee is locally roasted and sustainably sourced, and the beers on rotation match Portland’s high bar for inventive and thoughtfully crafted beer.