City Cast Portland logo

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.

More on May in Portland

Share article

Hey Portland

Stay connected to City Cast Portland and get ready to join the local conversation.

Can't subscribe? Turn off your ad blocker and try again.

Portland's Best

See All

The latest in Portland

The Weekly Wander by City Cast PortlandSeptember 13

Side Quest: Charting History’s Course

While most of the Overlook neighborhood sits above the bluffs, the industrial area of Swan Island down below does actually fall within it...

An aerial photo from 1935 shows the Swan Island airstrip, built on a peninsula that juts out into Portland’s Willamette River.
The Weekly Wander by City Cast PortlandSeptember 13

Your Guide to Overlook

Beyond the views, the North Portland neighborhood has plenty of perks: access to the MAX Yellow Line, cocktail lounges, and residents who...

Branches with green leaves frame a view of Portland’s Fremont Bridge with skyscrapers behind it.
The Weekly Wander by City Cast PortlandSeptember 6

Side Quest: Pre-Game Routine

We don’t want to throw you off your game, but we do have some fun suggestions to spice up your traditions on the way to the Rose Quarter...

Banners and window art on the Moda Center show Portland Trail Blazers figures and history. In front of the arena, a person rides a bike by a sign that spells out Rip City.
The Weekly Wander by City Cast PortlandSeptember 6

Your Guide to the Lloyd District

For 66 years, the Lloyd Center was a place where Portlanders made memories, went shopping and ice skating, and even put in the miles mall...

An aerial shot shows the roof and twin glass spires of the Oregon Convention Center, with high-rise office buildings of the Lloyd District in the background.
Portland Life HacksSeptember 1

Tips for a Better September 2026 in Portland

September is still summer in Portland, with outdoor events, farmers markets, and a major traffic disruption to plan around.

People in lawn chairs and on grass in front of a stage with the sign “Jazz Festival” visible.
The Weekly Wander by City Cast PortlandAugust 30

Your Guide to the Pearl District

Portland’s largest outdoor art fair is celebrating its 30th anniversary Saturday, Sept. 5 through Monday, Sept. 7 under the trees in the...

People browse artist booths under the trees at Art in the Pearl. In the foreground, colorful glass sculptures sit on pedestals.
The Weekly Wander by City Cast PortlandAugust 30

Side Quest: Art in the Heart

Born from Portland’s creative warehouse scene, the Pearl District remains an arts hub, with galleries, museums, public art, and vibrant c...

A colorful abstract painting of a person hangs on a wall to the left. In the background, two figures observe different paintings at the Froelick Gallery in Portland, Oregon.
Portland, ExplainedAugust 27

How Well Do You Know Our Local Mascots?

Portland Fire, the city’s WNBA team, revealed their new mascot this week after much fanfare.

Pink dragon in a Fire jersey.