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City Cast Portland

City Cast Portland

☀️ Is Portland the best summer city?

July 3, 2025 · — Rachel Monahan

Good morning, Portland! We’re gearing up for a long holiday weekend, so we have something different for your inbox today: some expert recs on how to explore Portland this summer, along with a special quiz designed to help you find a summer trip that fits your vibe.

And heads up, we’re off tomorrow so we won’t be back in your inbox until Monday. Try not to miss us too much, and enjoy those fireworks (also, if you’re looking for a quick anecdote to sound smart at the BBQ, check out this piece on how the Independence Day fireworks tradition began.)

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Summer Starter Pack

Best Local Bike Outings

Summer in Portland means getting outside. And you don’t even have to go to the coast or the Columbia Gorge to enjoy summer. We have some suggestions for the best local bike trips to enjoy the warm, sunny weather in town (and just beyond). [City Cast Portland]

Explore Sidewalk Joy

You’ve probably heard of little free libraries. Portland has plenty of those, but also something even quirkier — sidewalk displays that offer free exchanges for Croc charms, crafting supplies, and rubber duckies, not to mention miniature art displays. There’s even an official map of all this sidewalk joy, so take a bike ride or a walk and explore this city fun. [City Cast Portland]

screenshot of the 13 City Cast podcast hosts sitting before mics
Podcast hosts from the 13 City Cast podcasts smile as they spar for bragging rights.

Is Portland the Best for Summer?

City Cast podcast hosts from around the country came together for a high-stakes showdown, competing to do justice to their city’s summer offerings: Which city is the best for a summer weekend trip? From naked bike rides to ‘the country’s best farmers market,’ pickle festivals to Elvis impersonators driving pink convertibles, our hosts are bringing the best of the best of what their city has to offer. And yes, we do pick a winner. [City Cast Portland]

screenshot of a podcast player

Where Should You Plan Your Next Summer Weekend Trip?

Images of the skylines in Austin; Chicago and Pittsburgh
Which City Cast city should you visit this summer? From left to right: The skylines of Austin, Chicago, and Pittsburgh. (Brandon Bell/Getty Images; Jacoby Cochran/City Cast Chicago; Jeff Greenberg/Universal Images Group via Getty Images)

While our 13 City Cast cities (Austin, Boise, Chicago, D.C., Denver, Houston, Las Vegas, Madison, Nashville, Philly, Pittsburgh, Portland, and Salt Lake) duked it out in our most recent podcast episode, debating which of our cities is the best for a long weekend trip, we wanted to give you the chance to find the city that best suits your summer vibe.

Would you rather eat at a kitschy Mexican restaurant with a 30-foot waterfall and cliff divers — or explore a pickle-themed festival spread across two scenic bridges? Do you want to embark on a naked bike ride (which doubles as a protest) or kayak down a historic river? The choice is yours!

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What To Do

Thursday, July 3

Friday, July 4

Saturday, July 5

Sunday, July 6

🌭 An estimated 150 million hot dogs will be eaten on the Fourth of July, according to the esteemed National Hot Dog and Sausage Council. That amount of weiners would stretch lengthwise across the country (from NYC to PDX) at least five times. Take this as your sign to use hot dog lengths as your standard unit of measurement this weekend. How far is it to the neighbor’s BBQ? 57 hot dogs. Where’s the nearest coffee shop? 456 hot dogs.

Have a great Fourth of July! See you Monday 😎

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