Once viewed as a hidden gem snuggled among clouds and trees in a soggy corner of the country, Portland has undergone an image makeover in the last 10 years. It’s now on every major travel and food magazine’s lists of must-visit destinations, offering off-the-grid gems for all ages. And even though it’s not quite the weird gem of a town I fell in love with as a kid, many of the Rose City’s institutions that gave it its reputation of being “endearingly different” are still there; you just have to look a little harder.
Here are eight essential, must-see Portland icons to visit this fall.
There are a million coffee shops in Portland, and a fair amount of them serve a decent cup of joe. But for a delicious roast that doesn’t come with a crowd, head down to Water Avenue Coffee. Located in the city’s Central Eastside Industrial District, a part of town slightly blighted and still full of character because of zoning regulations, Water Ave serves tasty blends and teeth-chattering cold brews in a cozy environment usually filled with the tunes of a local indie band.
The shop hasn’t been around forever—it popped up during the recession in 2009—but its first-rate coffee and close proximity to the city’s heart have made it a favorite for Portlanders of all walks of life, from city government officials to metal heads.
Not far from Water Ave, bobbing gently on the Willamette River and in the shadow of the Hawthorne Bridge, is one of Portland’s beloved off-the-map landmarks. Known simply as “The Dock” by locals, this anchorage spot for river paddle boats provides an epic and unimpeded view of the city’s skyline — in other words, your best chance for a well-liked Instagram post.
The view is beautiful and stunning all year round, and with the space largely free of rules and so close to downtown, it’s the type of picturesque gem that you’d expect to find in a movie and not in real life.
Sadly, many of Portland’s record stores have gone instinct over the past five years. Its crown jewel of shops still remains, however, in Music Millennium. Now with only one location on East Burnside (it used to have a second location on 23rd Avenue), MM is still the best spot in town to discover and purchase music.
Some advice: Ask the counter clerks for recommendations of local bands to check out. Let those recommendations, regardless of how weird and daunting they may be (I was last suggested a local death metal band), be the soundtrack for your visit. The city is a hub for intimate and experimental music, and its bands will put you in the right state of mind as you explore it.
There’s never been a better time to check out cannabis tourism in the Rose City. Shango runs a range of state-of-the-art cannabis facilities across Oregon, touching every part of the industry from cultivation operations to retail.
Their Shango Harold location in Southeast Portland is a slick, stylish production designed to give cannabis patients a premium experience every time they visit. The staff are friendly and knowledgeable, and because Shango stocks cannabis grown at their own facilities, customers know what to expect from their purchase.
You’ll find the Rose Garden on most “must-visit” lists for Portland, but believe the hype—it truly is an enchanting place to see. The city’s cool and damp conditions make it the perfect growing ground for the rose plant, and the garden is a grandiose display of that gift.
The first thing you’ll see as you enter the park is a stop sign drowning in a knoll of crimson-colored flowers, and the abundance and gaudiness of things only go up from there. With around 550 varieties of roses on display, the garden is literally a testing ground for the plant. One walk through its grounds will reveal a number of one-of-a-kind flowers, from thin, star-shaped pink roses to monstrous purple ones.
To sweeten the experience, Washington Park sits on a hill above Portland, providing stunning views of the city and snow-peaked Mt. Hood on a clear autumn day.
If you’re in PDX, you gotta get a little weird. That means taking a break from the well-lit breweries of the Pearl District and taking a trip toward the city’s Chinatown area, where eclectic businesses like Voodoo Donuts first gained infamy through blasphemy.
The best watering hole in this neighborhood is Dante’s, an intimate venue with thrills as cheap as its beer. A surprising number of notable bands play here every month, but for best results check out one of its weekly in-house performances, like Who’s The Ross? Hosted every Tuesday by local comedian Aaron Ross, the late-night talk show is built on hilarious—and often vulgar—skits that usually involve bad wigs, burlesque dancers, and sex toys. It’s the perfect place to sip on a Pabst while appreciating the city’s stranger side.
As demonstrated by a skit in the television show Portlandia, Portlanders don’t mess around when it comes to brunch. Lines form early and can sometimes span entire city blocks. Personally, I think it’s all a little silly, but one place I will make time for is Tasty N Alder, located near West Burnside Street.
Opened by local chef extraordinaire John Gorham, the restaurant is technically a steakhouse but feels more like a family-style café. The dishes are decadent, delicious, and usually feature a juicy cut of meat that’s been rendered into mouth-melting goodness. This makes for some interesting brunch dishes, like Korean friend chicken, buttermilk biscuits with bacon lardons, and even duck steak. Go big or stay home.
One of the big selling points of Portland is that the city is not far off from almost every kind of natural environment you can imagine, including mountains, deserts, and beaches. The city itself also contains a massive park in its limits (Forest Park), as well as a majestic mass of farmland, orchards and shorelines in Sauvie Island.
The island, which sits between the Willamette and Columbia Rivers and is only about a 25-minute drive from downtown, is the spot that every Portlander dips out of work early on Fridays in the summer to go to. Its breezy river beaches are perfect for cooling off on, but its quiet and lush landscape can be enjoyed really all year long, whether you’re picking pumpkins at Kruger’s Farm in the fall or having a picnic under a random oak tree somewhere on the island in spring.
No trip to Portland is complete without some sort of outdoor activity, and venturing to Sauvie Island is a good one.
Are you going to Oregon for its recreational cannabis? Make sure you download our 101 Guide to Recreational Cannabis in Oregon!
Image credits: Music Millennium via James Allenspach on Flickr; International Rose Test Garden by Matt Lehrer on Flickr; Dante’s via Christien Reed – Concert Co-Op on Flickr; Sauvie Island via Dani Tinker on Flickr
This article was updated September 27, 2016.