Your Guide to May 2025 in Portland
Whether you’re chasing reservations at Portland’s best seasonal restaurant pop-ups or hitting the streets on a new custom skateboard, May offers plenty of excuses to step outside and enjoy our city's sunniest season. City Cast Portland has handpicked the absolute best of the month’s food, entertainment, and community happenings to help you narrow down your plans to this month's must-dos — like signing up for a local farm CSA.
Plus, a bonus suggestion from our episode archive: Why Spring Is the Perfect Time To Visit Oregon’s High Desert
If you're new here, welcome! We’ve put together a starter pack for you, with episodes and articles to welcome you to the City Cast Portland community.
For even more tips on how to make the most of May in Portland, check out Hey Portland’s take on what to do this month.
Join City Cast Portland at the 503 Day Block Party, Saturday, May 3, at downtown Portland's Ankeny Alley!! Details and RSVP here.
City Cast Portland is also powered by our members, who enjoy an ad-free version of the show. Find out more about how to become a member of City Cast Portland.
Interested in advertising with City Cast? Find more info here.
Reach us at portland@citycast.fm.
Learn more about OMSI, the sponsor of our May guide
And learn more about the other sponsors of this May 1st episode:
- Aura Frames - Get $35-off plus free shipping on the Carver Mat frame with Promo Code CITYCAST
- Clackamas County Masters Gardeners Association
- Rose City Comic Con
Learn more about your ad choices. Visit megaphone.fm/adchoices
Subscribe To Our Newsletter

Stay connected to City Cast Portland and get ready to join the local conversation.
Latest Episodes
Your Guide to August 2026 in Portland
Whether you’re riding bikes to the cutest curated public art galleries, roller skating to some local hip-hop, or trying delicious Hawaiia...

City Gets Sued for $717K Over a Single Tree, Why Nextdoor is the Worst, and Theories on All Those Loud Booms
We’re talking about how a single tree cost the city over $700,000 and a new local alternative to Nextdoor promising less snark and more c...

Mayor Keith Wilson on Keeping the Blazers, Fixing 911 Response Times, and His Efforts To End Homelessness
Portland Mayor Keith Wilson is joining host Claudia Meza to talk about how things are going nearly halfway through his term. We’ll be cha...

Is Portland Really Better Than Seattle?
Today, it's Portland vs. Seattle. Which city is actually better? We're listening back to a conversation with Jane C. Hu, host of City Cas...

‘Your City Could Be Better’: The Trick to Getting People To Volunteer — Presented By City Cast Portland
It’s not a given that every Portlander will chip in to help their community. In this episode, City Cast CEO David Plotz talks with writer...

Does City Council Have a ‘Daddy’? Plus, Oregon’s Outdated School Funding Formula and Shady Landlords
We're talking about a Portland renter beating his landlord in court and Mayor Wilson's tie-breaking vote on a City Council ordinance and...

Why No One Is Happy With the Moda Deal. Plus, Preschool for All’s Uncertain Future and Listener Maibag
We're talking about the latest in the ongoing Moda Center negotiations, and why Preschool for All might need fewer seats in the coming ye...

Why Portland Is at Risk of an LA-Style Wildfire. Plus, We Beat Seattle in a World Record and Intel in Trouble
We're talking about the Guinness World Record our city just broke, why an energy expert is sounding the alarm that Portland is at risk of...

The Most Overrated (and Underrated) Portland Summer Activities
We're talking about our city's most overrated and underrated summer activities. Yes, we've got gripes but also tips about how to get the...

Why Fox News Hates the Portland Pickles. Plus, More Financial Trouble for Home Forward and Our Top Summer Drink Spots
We’re talking about the news that Portland’s housing authority, Home Forward, is in a bigger financial shortfall than previously reported...


