Where To Play This Weekend in Portland: Events, Dining and Local Picks
This weekend, August 22 to 24, 2025, the city’s neighborhoods and parks light up with festivals, flowers, and film. Here is your insider guide to savoring every bit of it.
🟢 Where To Eat
photo: eatoysterbar.com/
Pal’s (Hayden Island)
A breezy new waterfront restaurant where the Columbia River meets bold seafood driven fare. Try the kettle chip crusted rainbow trout sandwich or the teriyaki salmon bowl with roasted broccoli and cabbage slaw. Finish with soft serve or browse the small market.
EAT: An Oyster Bar
3808 N Williams Ave, Portland
A North Williams staple and creole‑Cajun raw bar with a rotating lineup of Pacific‑to‑French oysters, oyster shooters, gumbo, fried catfish, and Southern cocktails. Home to lively weekend brunches, rotating daily offers, and a $125/year Oyster Club that delivers a dozen oysters monthly.
Portland Spirit (South Pearl District)
With a small fleet of boats ready to show you a unique side of Portland, the Portland Spirit experience is one to look into. Book a sightseeing tour, a full meal, or even a special trip to see the lower Columbia River Gorge! Book early, these tours fill up quickly this time of year.
🔵 Where To Stay
Old Town Chinatown
Bookend your weekend in Portland’s historic district. Enjoy rooftop cocktails at Departure Lounge, Pacific Northwest Mexican flavors at Lilia Comedor, and dim sum at Xin Ding Dumpling House. The district is walkable, artful, and full of unexpected delights.
Waterfront Retreats
Stay near Hayden Island, where boutique inns and riverside rentals keep you close to fresh seafood and outdoor escapes. Perfect for those who want calm mornings on the water with easy access to city energy.
🟡 Where To Play
Hawthorne Street Fair
Sunday, August 24, 11 a.m. to 5 p.m. between 34th and 38th on Hawthorne Boulevard. Portland’s classic summer festival with more than one hundred vendors, food carts, music, and family friendly fun. Free entry.
Kidz Outside Festival
Saturday, August 23, 6:30 to 8:30 p.m. at George Park in St Johns. A grassroots celebration with music, performances, giveaways, and plenty of joy. Free entry.
The Goonies Fortieth Anniversary Screening at OMSI
Friday, August 22 at 6 p.m. with additional screenings all weekend. Relive the adventure in the Empirical Theatre at OMSI. Tickets range from sixteen to twenty one dollars.
Sunflower Fields and Dahlia Displays
All weekend at regional farms including Bella Organic, Lee Farms, Topaz, O’Keefe, Wooden Shoe, and Swan Island. A seasonal spectacle with blossoms in every direction. Entry ranges from free to twenty five dollars depending on the farm.
Willamette Shore Trolley
Running weekends through early fall. Climb aboard a replica streetcar for a ride between Bancroft Street in Portland and North State Street in Lake Oswego. The journey includes a century old tunnel, sweeping river views, and a nostalgic atmosphere.
photo: wst.oregontrolley.com/
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