The Waterfront Blues Festival always arrives with a bang on Fourth of July weekend. | Photo by @waterfrontblues
From music festivals to free, family-friendly events, Portland buzzes with energy in the summer. Lucky for you, we put together the biggest events to plan for taking place throughout the city next month.
Take out your calendar, grab your day planner, or text all your friends — these are the top three events we recommend heading to in July.
Waterfront Blues Festival| Friday, July 4-Saturday, July 5
Happiness is sitting by the river taking in shows from a comfy lawnchair. Headliners have yet to be released for this year’s fest, so stay tuned for updates.
Summer Free For All| Thursday, July 10-Saturday, Aug. 30
More than three dozen free events will take place across Portland, ranging from screenings of kids’ classics like “The Sandlot” to arts festivals. Take a look at the full calendar.
Portland Pride Festival & Parade | Saturday, July 19 + Sunday, July 20
Expect a weekend chock-full with exhibitions, vendors, entertainment on multiple stages, and lots and lots of community.
Live Music Thursdays | Thursday, June 26 | 5-8 p.m. | Amaterra Winery | $25 | Embrace the weekend vibes early with seasonal bites, a glass of wine, and live jazz on the terrace — this week, Caleb Paul will perform.
Friday, June 27
Barre3 + Bubbles at Argyle Winery | 9-10 a.m. | Argyle Winery, Dundee | Free | All levels are welcome to this free Barre3 workout on the patio, followed by a complimentary pour from Argyle, bites, and a raffle — bring your own yoga mat and water.
Oregon Midsummer Festival | Friday, June 27-Saturday, June 28 | Times vary | Nordic Northwest Campus | $15+ | Celebrate Midsummer with flower crowns, crafts, games, live music, and of course, a Midsummer pole.
Saturday, June 28
2025 Portland’s Funniest - Preliminary Round | Saturday, June 28-Wednesday, July 30 | Times vary | Helium Comedy Club | $20+ | Help crown the Funniest Person in Portland — contestants move on based on audience votes.
Picklefest | 7 p.m. | Walker Stadium | $14+ | Engage in more than just baseball at this Portland Pickles game: this festival also features local beers, onsite tattoos, activities, and more.
Sunday, June 29
Portland Flea | Sunday, June 29-Sunday, Sept. 28 | 11 a.m.-4 p.m. | The Redd on Salmon | Free | Shop from a curated lineup of 100+ vendors selling clothing, craft goods, art, and more — and don’t miss the food, drinks, and treats at The Lunch Counter.
Pride Beaverton’s Pride in the Park 2025 | 11 a.m.-5 p.m. | Beaverton City Park, Beaverton | Free | The eighth Pride in the Park starts with a march through downtown Beaverton and ends with a festival featuring vendors, drag performances, and awards.
Hop aboard a two-and-a-half-hour sunset dinner cruise down the Willamette River. With golden hour lighting up the skyline and waterfront, Portlanders can snag a ticket to enjoy:
A three-course plated dinner with entrée options that highlight the best of Northwest cuisine (take a peek at the sample menu)
Live piano music
A private, candlelit table
Optional historic narration from the outer decks
And unbeatable views of downtown Portland, Lake Oswego, and the Historic Milwaukie Waterfront
Whether it’s date night, a birthday, a unique outing with friends — or just a treat-yourself Tuesday — this is one of the best ways to capture the heart of summer in the Pacific Northwest.
And honestly, who doesn’t love a reason to slow down and enjoy the view?
If you were planning to hit the water for the Fourth, take note. Lake Oswego will be barred from public access from Thursday, July 3 to Monday, July 7 due to concerns about public safety during the Fourth of July weekend. (FOX 12)
Holiday
While we’re talking about public safety on the Fourth of July, here’s a reminder that the City of Portland has banned fireworks usage within city limits. Fireworks are also prohibited at Oregon State Parks + on the entire Oregon oceanfront. (Columbia Gorge News)
List
Portland is a top food truck city in the US, but we already knew that. Yoshi’s Sushi (No. 15), Bake on the Run (No. 18), and Iolani’s Plate Lunch (No. 20) all ranked highly on Yelp’s list of Top 100 Food Trucks 2025, but four more local spots also made the cut.
Portlander
Tumwater Middle School student Isha Marla is one of 10 finalists for this year’s 3M Young Scientist Challenge, a prestigious national science competition. Marla will participate in a summer mentorship program with a 3M scientist to advance a scientific solution for the chance at the $25,000 grand prize. We’re rooting for you, Isha.
Announced
After 24 years, the Portland Tribune will cease printing papers in favor of online-only content. The paper’s sister publications in Milwaukie and OregonCity will also end print editions + the Gresham Outlook will transition to one print edition per week instead of two. (Oregon Live)
Trending
Zac Woodworth, a 26-year-old Portlander, is one of the newest contestants on this season of “Love Island USA.” According to his introduction, Woodworth is “down to find someone to take over the world with” — to see if he succeeds, stream the show every night but Wednesday at 6 p.m.
Sports
Now that the NBA season’s over, it’s draft time. Follow along on how the Trail Blazers are faring with the local experts of the Portland Trail Blazers with Locked On’s daily podcasts.
Shop
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The basics you need while they’re on sale. Amazon Basics just marked down tons of products in a sale exclusive for Prime members — time to restock the bathroom/office/supply closet shelves:
The fun doesn’t have to end here. After reading the newsletter, head over to our games page. Games refresh with new challenges every day at 6 a.m. from crossword puzzle to Sudoku to themed word search.
Broadway in Portland’s 2025/2026 season lineup is here, and I’d like to see every one of these shows. Highest on my list? “Les Miserables,” “Mamma Mia!” and “Shucked.”
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