What to Do in Oregon in September

Image: Vibbily / Alamy
Between the Time-Based Art Festival, Rose City Comic Con, dragon boat races, and the annual roosting of the swifts (wherever they roost), September offers no shortage of reasons to stay in Portland. But these last weeks of summer are also a prime time to get out and explore Oregon, from blooming flower fields to the state's biggest rodeo to coastal car shows and multiple Oktoberfests. Prost!

Annual Dahlia Festival
Thru Sept 30 | Canby
Canby's family-owned Swan Island Dahlias counts more than 375 varieties in its 50 acres of fields, which open to the public in August and September for strolls, picnics, and plein air painting sessions. Also on offer: classes on dahlia care, yoga sessions, daily food carts, and live music on Saturdays and Sundays.
Ride the Rim
Sept 6 & 13 | Crater Lake National Park
For two Saturdays in September, most of Crater Lake's Rim Drive closes to vehicle traffic, giving cyclists the run of the road from 8am to 4pm. Participants need only register in advance and pay the park's entry fee—the ride itself has no additional cost. This year, registration closed early due to "overwhelming participant response." (Maybe the rush has something to do with upcoming closures, as some park sections and trails—including access to the lake itself—will be off-limits to visitors from next year until 2029.) If you missed your chance to ride, find a spot to watch like it's a stage in the Tour de Oregon.

Pendleton Round-Up
Sept 6–13 | Pendleton
Dress-up parades, pageants, rodeos, concerts: for 115 years, the Pendleton Round-Up has been the festival for celebrating western heritage in Oregon. Expect roping, barrel racing, Happy Canyon night shows, a Junior American Indian beauty contest, outdoor cowboy breakfasts, and more. So strap on your boots, fix your bolo tie, and dust off that 10-gallon hat, pilgrim. We’re headin’ to the rodeo.
Oregon Hop Festival
Sept 6 & 7 | Woodburn
Oregon has its fair share of brewfests, but this gathering celebrates the state-grown cones that give our beers their bite. Oregon Hop Fest returns with two full days of beer tastings, guided tractor tours through the fields of Crosby Hop Farm, a hop-sniffin' station, live music, and food vendors.

Mt. Angel Oktoberfest
Sept 11–14 | downtown Mt. Angel
Whip out your lederhosen, grab your dirndl, and definitely take a designated driver to this annual beer fest in this otherwise sleepy town. Some of the harder-partying tents have an admission fee, but you can also just stroll around and pay only for your beer, pretzels, and sausages. A free kindergarten hosts pony rides and face-painting for the very-under-21 crowd.
AIDS Walk Northwest
Sept 13 | Tom McCall Waterfront Park
Since the ’80s, thousands of community members in Oregon and Washington have joined Cascade AIDS Project on an annual walk to reduce stigma, raise awareness, and remember and celebrate the lives of those lost to HIV and AIDS. As federal funding cuts to HIV/STI prevention and LGBTQ+ health care sweep the nation, AIDS Walk Northwest is vital to sustain CAP’s HIV services. This year’s walk will be emceed by the legendary drag queen Poison Waters.
Cascade Equinox Festival
Sept 19–21 | redmond
This fledgling music fest returns for a third year of electronic, funk, soul, and bluegrass concerts at the Deschutes County Fairgrounds. Headliners include electropop duo Sylvan Esso, the multi-instrumental and genre-colliding EDM group Big Gigantic, and GRAMMY-nominated electronic duo Disclosure. On-site camping, movement and herbalism workshops, a spa-esque zone, live art, and a bevy of food and drink vendors round things out. Both weekend and single-day tickets are available.

Bay Area Fun Festival
Sept 20 & 21 | Coos Bay
No, not the San Francisco Bay Area. This fun fest happens in Oregon's version, the Coos Bay area, and includes a Cruz the Coos car show, the Prefontaine Memorial Run (the legendary distance runner was born in Coos Bay in 1951), a parade, live music, and general celebration of the town's 150th birthday.
Corvallis Fall Festival
Sept 27 & 28 | Corvallis
What’s the old saying? Ask and ye shall receive. It’s kind of what happened in the ’70s in Corvallis, when residents pestered the city with questions about why there was no arts festival in town. Persistence was key, and in 1973 the very first Corvallis Fall Festival got off the ground. Now, the mostly free event features arts and crafts booths, food vendors, live music, a Saturday-night street dance headlined by Too Loose Cajun/Zydeco Band’s Louisiana-style dance hall music, interactive art activities, and a trio of runs (registration fees apply for the 5K and 10K, but there’s a free 1K for kids).
Oregon Alpenfest
Sept 24–28 | Enterprise, Lostine & Joseph
This Wallowa County event bills itself as Swiss-Bavarian, with more yodeling and alphorn playing than you’ll find in Mt. Angel, not to mention more mountain views of the area known as Oregon’s Alps. It’s a much longer drive than to Mt. Angel, too—if you want to embark on a beer road trip, here are two taverns to hit in the region.