What to Do in Oregon in October
Costumed paddlers square off in the West Coast Giant Pumpkin Regatta.
While October is a perfectly good time to hole up in the kitchen making kimchi stew and apple pie, or stick to happenings in town and nearby day trips, there’s also plenty going on elsewhere in Oregon, indoors and out, to pull you out of Portland proper.
Thru Sun, Oct 26 | Ashland
The 2025 Oregon Shakespeare Festival opened in March and comes to a close at the end of this month. There’s still time to make the jaunt to Ashland for The Importance of Being Earnest, Shane, Quixote Nuevo, and Into the Woods, as well as Shakespeare titles Julius Caesar, As You Like It, and The Merry Wives of Windsor.
Oct 1–31 | Various locations
Get a taste of Oregon’s northern coast at this food-focused festival that extends from Astoria to Neskowin. Previously a single-day event, the festival now runs through the entire month of October with culinary events and weekly prize drawings. Participating restaurants, markets, and artisans will offer signature “Crave Dishes” made with locally sourced ingredients.
Fri–Sun, Oct 3–5 | grants Pass
The Southern Oregon city of Grants Pass hosts this 22nd annual festival, when chalk artists turn several downtown blocks into their canvases. This year’s theme is The Timewarp, bringing the past and the future together in the festival’s street chalk murals. Expect live music all three days, too.
Fri–Sun, Oct 3–5 | Bend
For nearly 30 years, this festival has covered six city blocks of downtown Bend each fall. With most of the summer crowds thinned out and winter ski season still a few months away, autumn makes for a quieter time to visit the mountain town. You will find a harvest market, pumpkin painting, an arts and crafts market, food and drink vendors, and live music.
Sat, Oct 4 | Portland
Bathe your smelly pup, treat yourself to a beer, and donate to a good cause at DoveLewis’ dog wash fundraiser for its lifesaving blood bank. Located at Lucky Lab on Hawthorne Boulevard, the event features bubbly baths for dogs and a photo booth. Entry is free, but donations for the blood bank are encouraged.
Sat, Oct 4 | Roseburg
Roseburg’s fourth 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.
The Hood River Valley, home to an impressive collection of apple orchards and hop bines.
Sat, Oct 4 | Hood river
Typically, on the first Saturday in October, the Hood River Valley hosts a celebration of hops. This 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, alongside live music and food and craft vendors. Entry and tasting packages run $13–37 and the under 21 crowd is free.
Fri–Sun, Oct 10–12 | Hood River
A week after the orchard and ale festival (see above), this 43rd annual harvest fest is a little closer to Hood River’s 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. Admission runs $10–12 per day, $20 for a weekend pass, with $5 tickets for seniors and military on Friday only. Kids 12 and under are free every day.
Wed–Sun, Oct 8–12 | Bend
Catch some indie films during Bend’s annual fest of screenings and filmmaker discussions at theaters and venues across town. This year, the film festival celebrates its 22nd year with an expanded five-day format. Twenty-four 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.
In the Great Columbia Crossing, runners tackle the 21,474 feet of the Astoria-Megler Bridge.
Sun, Oct 12 | Astoria
This year’s 10k run/walk over the Astoria-Megler Bridge hit its 3,500-person registration cap in mid-July in its fastest sellout on record. 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 2026 registration opens next summer.
Fri–Sun, Oct 17–19 | Yachats
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 few of the talks are free, and the walks run $5. Also, look for an all-things-mushroom faire of fresh fungi, gourmet products, and handmade goods from local artists and foragers.
Oct 17–Nov 4 | Portland
Milagro Theatre’s annual Día de los Muertos festival returns for its 30th celebration with the production of Georgina Escobar’s ¡Alebrijes! A Día de Muertos Tale. The play pays homage to Pedro Linares, a Mexican papier-mâché artist who created colorful sculptures of dreamlike creatures often associated with the holiday. The festival also celebrates the Day of the Dead with altar displays, alebrijes and altar workshops, bike rides, and a community dinner and fundraiser.
Costumes are required at the West Coast Giant Pumpkin Regatta.
Sun, Oct 19 | Tualatin
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. Twenty 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, we rustled up tips from a regatta champ.
Fri, Oct 24 | Bend
The High Desert Museum’s popular speaker series featuring Indigenous artists, scholars, and storytellers returned in September. This month, Nez Perce language expert, educator, and storyteller Harry Slickpoo Jr. will present his work as an advocate for nimiipuutímpt, the Nez Perce language and culture. Tickets are $5–20 and free for tribal members.
Sun, Oct 26 | Eugene
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, and mushroom, craft, and food vendors. Ticket sales open September 26.
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