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What To Do in Portland in May 2025

Posted on May 1, 2025   |   Updated on September 30, 2025
City Cast Portland staff

City Cast Portland staff

Veggies laid out on a wood countertop.

Veggies courtesy of a CSA from a local farm. (John Notarianni / City Cast Portland)

City Cast

Your Guide to May 2025 in Portland

00:00:00

It’s getting warmer and sunnier, and that means more chances to stop hiding in our homes, eat outdoors, and get local produce. We have some related tips for enjoying May to the fullest.

Plus, here are a few fun events to start off your month:

  • 🪵 “The Log Lady” Exhibit: This one opens today — and is for all you “Twin Peaks” fans. Actress and Oregonian Catherine “The Log Lady” Coulson became a real-life advocate for forests. The World Forestry Center's new exhibit tells her story. Diehards are encouraged to come dressed as The Log Lady for a lookalike contest on May 17.
  • 🎉 503 Day (Obviously): On Saturday, we’re celebrating Portland with a block party. You’re coming, right?
  • 🇲🇽 Cinco de Mayo Fiesta: Beginning tomorrow and throughout the weekend, the downtown waterfront festival will be celebrating its 38th year. Fun fact: Portland is sister cities with Guadalajara, Mexico. (If you want a marathon day of festivities Saturday: There’s also the Saturday Market and an Old Town night market.)

🍴 Warmer Weather Brings New Restaurant Popups

As bars and shops make use of their patios, it's the time of year for new seasonal restaurant popups. If you’re looking for new spots to eat, City of Popups has a guide for what’s around. (Hat tip to City Cast Portland podcast host Claudia Meza for that suggestion.) One idea for a must-try that’s been going on a year now: pizza nights at Bauman’s on Oak.

🫛 Sign Up for a Summer CSA

A lot of CSA’s start delivering their produce in June — or even later this month. So get yourself scheduled for a motherload of summer veggies. Here are some possible farms to get you started. (Hat tip to executive producer John Notarianni for this reminder.)

a new custom skateboard

A new custom skateboard from Tactics. (Giulia Fiaoni / City Cast Portland)

🛹 Design Your Own Skateboard

The warm weather is a chance to get back on your skateboard — or create your own. Senior producer Giulia Fiaoni designed her own custom skateboard at Tactics, a local snowboarding and skateboarding shop. You can get their suggestions based on whether you’ll be cruising or doing tricks.

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