What to Do in Oregon in October

The 2026 Oregon Shakespeare Festival opened in March and comes to a close at the end of October. There’s still time to make the jaunt to Ashland for shows including A Midsummer Night’s Dream, Emma, Come From Away, Yellow Face, and Smote This, A Comedy About God…and Other Serious $H*T.

Get a taste of Oregon’s northern coast at this food-focused festival put on by the North Coast Food Trail that extends from Astoria down past Tillamook, with fishing and crabbing charters, food tours, and restaurant specials.

The Southern Oregon city of Grants Pass hosts this 23nd annual festival, when chalk artists turn several downtown blocks into their canvases. This year’s theme is Reflections, inviting artists to “explore the many ways reflections shape how we see the world—from light dancing across water and images in a mirror to memory, identity, emotion, and changing perspectives.” Expect live music all three days.

With most of the summer crowds thinned out and winter ski season still a ways away, autumn makes for a quieter time to visit the mountain town. At this downtown event, which has been running for roughly 30 years, you’ll find a harvest market, pumpkin painting, an arts and crafts market, food and drink vendors, and live music. New this year: a Harvest Bake-Off for cooks who think their “homemade pie, fresh-baked bread, or signature chili has what it takes to impress.” 

The Seattle-born folk legend, a onetime piano prodigy who survived polio as a kid, has been recording since the 1960s. Now 87, she’s still gracing audiences with songs like her iconic cover of Joni Mitchell’s “Both Sides Now.” Judy Blue Eyes plays two shows in Oregon, and they’re both a bit of a hike: Friday, October 2, she’s at the Rogue Theater in Grants Pass, and the next night she comes north to Eugene before heading for the sunny Southwestern US.

Roseburg’s fifth annual fall festival is once again taking over the streets of its historic downtown. Expect local arts and crafts, food and drink vendors, live music, and family-friendly activities. The festival is free to attend, but to grab beer from one of the three bar booths, you’ll need to purchase a $5 mug and a handful of $2 tokens. 

Typically, on the first Saturday in October, the Hood River Valley hosts a celebration of hops. Last year, however, the hops fest rebranded by introducing hard cider, to better highlight the bounty of Hood River’s famous orchards. Still, much remains the same. Look for fresh hop beers and fall ciders from dozens of local brewers and cidermakers at the Hood River Event Site on the Columbia River waterfront, along with live music and food and craft vendors. Admission to the all-ages event is free, and tickets for tasting for those 21 and over start at $12.50. 

Catch some indie films during Bend’s 23rd annual fest of screenings and filmmaker discussions at theaters and venues across town. Narrative and documentary features will compete for juried prizes. Other highlights include a shorts program with films from sixteen countries. Full festival ticket costs range from $100 for students to an all-access pass for $325. Tickets to individual screenings run $15–17.

A week after the orchard and ale festival (see above), this 44th annual harvest fest gets even closer to the area’s agricultural raison d’être, with opportunities to load up on fresh pears, apples, pumpkins and other squash, honey, and more. Also on deck: live music, a bevy of food options, and a long roster of craft vendors. Tickets are $10 (those bought online in advance add a handling fee but are good all three days, while tickets bought on-site are just for that day), with $5 tickets for seniors and military on Friday only. Kids 12 and under are free every day.

Live music, face-painting, filbert play pits, beer and wine, a cider pressing, tractor rides, a flannel fashion show, and, of course, pumpkins fill the day for this fall fest at Tabula Rasa Farms, part of the Ground network.

Registration for this year’s 10k run/walk over the Astoria-Megler Bridge opened on June 1, and all 3,500 slots were sold out by June 7, beating the speed record set the year before. So if you’d like a chance to walk or run across the longest continuous truss bridge in North America (and you don’t suffer from acrophobia and don’t mind a little, or a lot of, wind), mark your calendars for when the 2027 registration opens next summer.

This Thursday Night Talk for the Clatsop County Historical Society looks at the local roots and lasting legacy of the goth screen queen, who was born Maila Nurmi and went to Astoria High.

Learn about edible and poisonous mushrooms of the Oregon Coast in hands-on workshops, guided walks, and talks about mushroom identification and truffles. Event prices vary, but a lot of the talks are free; walks run $10–25. Also, look for an all-things-mushroom faire of fresh fungi, gourmet products, and handmade goods from local artists and foragers.

Back in 2004, the Pacific Giant Vegetable Growers—a very real association of gardeners who raise behemoth gourds, tomatoes, watermelons, and more—plopped a few giant pumpkins in a man-made lake in Tualatin, hollowed them out, and paddled them across the shallow pool. More than 20 years later, the West Coast Giant Pumpkin Regatta is by far the southwestern suburb’s biggest annual event, drawing as many as 25,000 attendees (nearly the population of Tualatin itself) for its five rounds of races. While it’s too late this year to grow a pumpkin yourself, if you want to get in on the action next year, here are some tips from a regatta champ.

Bobbie Conner, director of the Tamástslikt Cultural Institute near Pendleton, comes to Bend to discuss tribal sovereignty as part of the High Desert Museum’s popular speaker series featuring Indigenous artists, scholars, and storytellers. Tickets are $8, free for tribal members, and registration is required.

Need more fun with fungi? Journey down to Eugene for this annual arboretum fundraiser, which includes guided nature walks by local naturalists, educational talks, cooking demos, live music, a scarecrow contest, an edible-vs.-poisonous display, and mushroom, craft, and food vendors. Ticket are $15, free for ages 12 and under.