Things-to-do-in-october-mt-angel-oktoberfest_3CEWEFG_yqp0ey What to Do in Oregon in September — The usually sleepy town of Mt. Angel will turn it up for Oktoberfest from September 12 to 15.

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!

swan-island-dahlias_1909863067_xtgndk What to Do in Oregon in September — We’re falling for dahlias in Canby.

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.

Sept 6 & Sept 13 | Crater Lake National Park

For two Saturdays in September, two-thirds of Crater Lake’s Rim Drive close to vehicle traffic from 8am–4pm, giving cyclists the run of the road. Participants need only register in advance and pay the park’s entry fee—the ride itself has no additional cost. This year, however, registration closed early due to overwhelming participant response (the lake will be off-limits to visitors until 2029). Instead, camp out by the trail and watch the race like it’s a stage in the Tour de Oregon.

pendleton-roundup-rodeo_P2EX71_avscwm What to Do in Oregon in September — More than a century on, the Pendleton Round-Up is still kicking.

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.

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.

mount-angel-oktoberfest_AP68KA_kia8hz What to Do in Oregon in September — Eins, Zwei, Drei, G’suffa!

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.

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.

Prefontaine-Kids-Running-courtesy_Oregon_s_Adventure_Coast_tdebxx What to Do in Oregon in September — In Coos Bay, mustachioed runners pay homage to Steve Prefontaine.

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.

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).

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.

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