Your Guide to May 2026 in Portland

May is such a lovely month. Here are some ways to make the most of it:

503 Day Celebrations | Sun., May 3

The City Cast Portland-inspired holiday to celebrate our city is back — on Sunday, May 3 (5/03), in honor of the area code. This year, Ankeny Alley and the Portland Bureau of the Transportation are hosting a street fair — like what we had last year. Karaoke From Hell as well as City Councilor Jamie Dunphy are among the performers. The mayor’s going to be there to ceremonially light up the new Pink District, a new entertainment district.

• Deals to celebrate: Mother’s Bistro will have a brunch cocktail — called a Think Pink Martini — for $5.03 from 9 a.m. to 2 p.m. Voodoo Doughnut is going to offer two Voodoo Dolls for $5.03 (regularly priced at $5 each); they’ll have a 503 Day message on them. At Kit Kat Club's bar, tap beers and well drinks will cost just $5.03.

🌷 Mother’s Day Brunch | Sun., May 10

If you’re looking to treat Mom mom right, there are some fancy options available for brunch:

• 🚢 Portland Spirit has a Mother's Day Brunch cruise ($124).
• 🍷 JORY at the Allison Inn and Spa has a three-course Mother’s Day weekend brunch ($55).
• Pal’s on Hayden Island is hosting a Mother's Day weekend bunch with the chef of a classic New England diner — Palace Diner in Biddeford, Maine.

Plus, Bridgetown Bites has a run-down of other tasty ways to treat Mom.

✅ Primary Election | Tues., May 19

Ballots have started going out for the primary election. There are competitive primary elections in some Oregon statehouse races as well as some judgeships. As always, it’s a good idea to consult the state voters’ pamphlet (it’s more like a book — you learn a surprising amount). And there are county specific ones (Multnomah, Washington, and Clackamas all have them).

• Newspaper’s editorial board endorsements: I recommend a read of the endorsements — even if you don’t necessarily agree with who they picked, you’ll learn something. The Oregonian has already endorsed candidates in some races.
• Willamette Week published their endorsement issue yesterday. Tip: Look for a newspaper box around town, since their website can be buggy.
• And also keep an eye out for the Portland Mercury's endorsements, which will be out soon.

Also happening this month are the downtown Cinco de Mayo celebration (May 1 - 5), St. Johns Bizarre (May 9), the Portland Rose Festival (starting May 22), and the centennial celebration of the Burnside Bridge (May 30).

Related: More suggestions on the podcast’s guide to the month.

Also: check back in with our events listings for more events throughout the month.