Road Trips

Concerts and Events Worth a Trip Out of Town This Summer

Willie Nelson, Taylor Swift, rodeos, big-time fairs, and more can be found in places around Oregon and the Pacific Northwest.

By Margaret Seiler May 24, 2023

The St. Paul Rodeo is held south of Portland over Fourth of July weekend.

While it's easy to pack a weekend or a whole summer with picnics, concerts, plays, and more without leaving Portland—or your quadrant, or even your neighborhood in some cases—there is more to the region that what's in the city. Here are a few lures that might pull you away from your usual haunts.


In damp, Doug fir–filled Cascadia it can be hard to remember that Oregon is the West, but dozens of annual rodeos in every corner of the state keep the connection. The Biggest Little Show in the World, a.k.a. the Sisters Rodeo, makes the already western town in Central Oregon really double down on the theme the second weekend in June. Close to Portland, the St. Paul Rodeo (June 30–July 4) has brought crowds to the Willamette Valley hamlet since the 1930s. Chief Joseph Days (July 25–30) kicks off with a Bucking Horse Stampede down Joseph’s main street. These all live in the shadow of the Pendleton Round-Up, one of the biggest rodeos in the world, which closes out the summer Sept 9–16 in the Eastern Oregon city. 

Seattle Envy

Our neighbors to the north kicked off their sunny season with a Stanley Cup playoff run courtesy of the Kraken. They’ll really be showing off July 11 as hosts for the Major League Baseball All-Star Game and all its attendant fanfare. Taylor Swift had to rub it in with not one but two nights in Seattle (July 22 & 23) while skipping Portland altogether. We’re guessing Amtrak will be packed and I-5 will be a parking lot that weekend, so we might skip the Capitol Hill Block Party (July 21–23), but Bumbershoot (Sept 2 & 3) has us eyeing the train schedule for Labor Day weekend, with Sleater-Kinney, Fatboy Slim, Sunny Day Real Estate, the Rebirth Brass Band, and more.

Serious Fairs

Multnomah has a lot going for it, but our little county fair in May can’t hold a candle to some of our neighbors’: Flo Rida headlines the Jackson County Fair in July, the Pig-n-Ford race is a draw at the Tillamook County Fair in August. The state fair, which had one of its biggest years ever in 2022 (organizers credited “pent-up demand” from the pandemic) runs Aug 25 through Labor Day. 

Fireworks over Wallowa Lake

Wallowa Lake Lodge's Birthday Party

The official birthday party for this 1923 lodge runs June 30–July 2, on the southern edge of Wallowa Lake in Northeastern Oregon. But you can stop by anytime in its centennial season (the lodge is open May–September) to wish it a happy 100th and check out the new bat houses, an effort to rehome the lodge’s longtime attic residents.

Bend and Redmond

At 90 years young, Willie Nelson headlines the FairWell Festival, July 21–23, at Redmond’s Deschutes County Fairgrounds, joined by Luke Bryan, the Turnpike Troubadours, Gary Clark Jr., Sheryl Crow, Nathaniel Rateliff & the Night Sweats, and some more local acts, including Y La Bamba and Haley Heynderickx. There’s plenty more rootsy action in the greater Bend area, too, with the Indigo Girls, plus Neko Case, playing Hayden Homes Amphitheater June 27, followed by Jason Isbell and Deer Tick at the same venue (the former Les Schwab Amphitheater) July 1. Can’t make it all the way to Bend? Indigo Girls and Isbell don’t have a Portland show, but they’ll be at the Clackamas County Fairgrounds in Canby July 1 and 2, respectively.

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