Portland’s spookiest month brings some of the city’s favorite events. Grab your rain boots and head to one of several nearby corn mazes and pumpkin patches, explore Portland’s haunted hot spots and catch a Portland Trail Blazers game. And don’t miss the city’s many celebrations of Halloween and all things scary. Read on for some of our favorite October events and things to do in Portland, or check out our full events calendar to see everything on offer.
Portland Trail Blazers
Watch the 1977 NBA Champion Portland Trail Blazers play at the Moda Center. Blazers fans cheer players on from October to April at the nearby Spirit of 77 and other local sports bars. While at the Moda Center, dig into local food and drink purveyors like Killer Burger, ice cream by Ruby Jewel and Salt & Straw, food cart favorite Tamale Boy and local brews at 10 Barrel Brewing.
Portland Film Festival
Portland has its fair share of film festivals, but Portland Film Festival is one not to miss. The week-long celebration of film that MovieMaker magazine called “one of the coolest film festivals in the world” is jam-packed with networking, workshops, guest speakers, film premieres, financing talks, director Q&As and more.
West Coast Giant Pumpkin Regatta
Watch as people seated in gigantic pumpkins race across a lake during the West Coast Giant Pumpkin Regatta. This free, wacky annual event is the only one of its kind on the West Coast.
Portland likes its scares as much as any other city and has the haunted houses to prove it. Some of the biggest annual options include Underhill Haunted House at the Moda Center and The Fear; Haunted Museum.
The Spirit of Halloweentown
The historic town of St. Helens, located 45 minutes from Portland, celebrates The Spirit of Halloweentown all month long with haunted tours, costume contests and more.
Portland Open Studios
Portland has a thriving art scene that is showcased during the monthly art walks happening year-round. However, every October during Portland Open Studios, artists all over the city open up their spaces to allow a glimpse into their artistic process and the chance to witness, first hand, the business of creative endeavor.
Portland has a well-established network of venues and theater companies and an increasingly dynamic and diverse small theater scene.
Classical music in Portland isn't just the classics. Classical musicians offer new and innovative works, and an ongoing lineup of inspiring performances, from timeless works to modern interpretations.
Portland dance has an inventive spirit that welcomes collaborations and often spills beyond the generally accepted boundaries of “dance.”
Hood River Valley Harvest Fest
The counterpoint to April’s Hood River Valley Blossom Festival is the Hood River Valley Harvest Fest. This is your chance to catch the tail end of the fruit-growing process. The fruit is picked and it’s time to party with music, food, wine and a quilt raffle. One hour and fifteen minutes from downtown Portland.
Family-owned Topaz Farm on Sauvie Island has a stunning corn maze by graphic design icon Aaron Draplin. Spread over seven acres, the corn maze has two entrances. The first entrance is ideal for parents of younger kids or people looking for a shorter stroll. The second entrance provides a truly challenging puzzle. Inside the maze…
The historic town of St. Helens, located 45 minutes from Portland, celebrates Halloween all month long with haunted tours, costume contests and more.
The Corn Maize, located on Sauvie Island north of Portland, offers visitors eight acres of physical and mental challenges in a cornfield.
Walk through Portland artist Mike Bennett’s immersive Crypto-Zoo: Museum of Mystery, filled with 26 life-size Cryptids, Monsters and Mythical Beasts. Play games, win prizes and look out for surprise guests.
The Parkrose Marketplace is an event aimed at giving more support and visibility to local small businesses and artists while providing a safe social event to connect with your neighbors, shop with great home-based vendors, and enjoy local food, coffee, arts & crafts. The Marketplace has over 60 vendors offering art, crafts, clothing, jewelry, culinary…
The popular Woodstock Farmers Market features fresh produce, baked goods, fresh juices, sweets, cheese, meat and more from 30+ vendors, along with artisan-made products like jewelry, ceramics and art.
This boisterous street fair attracts independent artists, performers, local bands, troupes of acrobats, buskers, makers and more to celebrate their art on Northeast Alberta Street. Held year-round, the event is biggest from June through August, when the street is closed to traffic during the festivities from 15th Avenue to 30th Avenue.
Started in 1986, First Thursday in the Pearl is a district-wide celebration that occurs on the first Thursday of each month. Originally a gathering of art collectors and dealers, the celebration has grown to a monthly event of over ten thousand people that includes art enthusiasts, wine aficionados, and scenesters looking to see and be…
The Curious Cabaret – A Riotous Vaudeville Revue is a monthly variety show hosted by Portland’s 20-time award winning physical comedy duo, A Little Bit Off. The show brings you the absolute best in top-notch local talent, with acts ranging from acrobatics and dance, to magic and juggling, with a whole lot of comedy in…
Portland Indigenous Marketplace supports indigenous artists and entrepreneurs by providing barrier-free, culturally respectful spaces that encourage cultural resilience and economic sustainability by promoting public education through cultural arts.
Taking runners along a loop of Portland along the east and west sides of the city’s Willamette River, the Portland Marathon is an excellent way to see a lot of Portland in one great run. The race starts and finishes at Waterfront Park, crossing four bridges and passing by some of the city’s most iconic…
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