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How to Enter the Portland Icons Costume Contest

Posted on April 14, 2025   |   Updated on September 30, 2025
City Cast Portland staff

City Cast Portland staff

a statue of Paul Bunyan wearing a white and red checkered shirt against a clear blue sky

Finally, a good reason to dress up like Kenton's Paul Bunyan statue. (Steve Morgan / Wikimedia)

[UPDATE 5/1] All the contestant slots for the costume contest have been filled

By now, you've most likely heard all about 503 Day. It's the totally real holiday we dreamed up to celebrate everything we love about Portland. Perhaps you've already signed up to attend. And now you're looking for a way to get even more involved. Well, guess what...

There's a Costume Contest!

The Portland Icons Costume Contest will be held live on stage as part of our 503 Day block party on Saturday, May 3. It's simple.

  • 📝 Sign up here
  • 👗 Dress as a 'Portland Icon'
  • 😅 Stand on stage
  • 🎤 Get judged by hilarious local personalities
  • 🏆 Win stuff!

Define 'Portland Icon'?

People, places, or things that represent our city. Bridges. Authors. Buildings. Tonya Harding. Use your imagination! If you have to awkwardly get on mic and explain your costume, that's fine too.

What's the prize?

All participants get an exclusive City Cast Portland tater tot plushie (yes, really)!

And our big first-place winner will get:

  • Glory, validation, bragging rights, etc.
  • A special spot on stage during the official 503 Day proclamation at 5:03 p.m.
  • 4 passes to Rose City Comic Con (for all three days)
  • A Portland Timbers 50th Anniversary jersey

Our esteemed judges include:

  • Claudia Meza (your beloved City Cast Portland host)
  • Jay Flewelling (local comedian)
  • Brianna Wheeler (Willamette Week reporter and author)

They'll score you on creativity, originality, and effort.

The fine print:

  • Keep it family-friendly. There will be kids around.
  • Limited to 15 contestants, first-come basis using our submission form.
  • Contest begins at 3 p.m. sharp. Be downtown at Ankeny Alley and ready by 2:30 p.m.
  • Not dressing up? Come cheer! It's more fun with a crowd.

Sign up today!

The deadline to enter is Wednesday, April 30. We need your name, email, and what you're planning to wear.

Sign Up Here

Need ideas?

Try these City Cast Portland podcast episodes:

Wait, what is 503 Day again?

503 Day is the totally real holiday we dreamed up last year to celebrate everything we love about Portland.

Thank you to our Gold level sponsors, including Rose City Comic Con.

  • Where: Ankeny Alley in downtown Portland (221 SW Ankeny St, Portland, OR 97204)
  • When: May 3, from 1 - 6:03 p.m. (5 hours and 3 minutes to honor our holiday!)
  • RSVP here. It’s free to attend.

You can expect live entertainment curated by the City Cast Portland team, food and drink, local luminaries, and much, much more. And, the city will officially declare it 503 Day at (you guessed it) 5:03 p.m.

Any questions? portland@citycast.fm

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