MANY Weekend Events & Giveaways ($1,400+): Halloween, Oktoberfest, Festivals, Concerts, Comedy, Theater, Film, & More!

A round up of what’s going on in Portland this weekend including festivals, concerts, comedy, trivia, happy hours, movies, & more!

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Related Events & Info:

• Next Week: Concerts, Comedy, Trivia, Theater, Happy Hours, & More!
• September: Our September Events Calendar + Giveaways
• GIVEAWAYS: Win Tickets to Concerts, Comedy, Festivals, Films, Theater, & More!
• Halloween: Events, Parties, Costume Contests, Haunts, Horror Films, Activities, & Giveaways!
• Jobs: Jobs Board – Creative, Tech, Construction, Green, Marketing, Service Industry, & More

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Portland Friday Events, September 25:

• Bikes: Carry Sh*t Olympics – Portland, OR’s Underground Cargo Bike Racing Event | Free, Scavenger Hunt, Friday Night Ride, Cargo Polo, & more (more info)
• Burger: Butcher’s Burger at Meatstuff (formerly Proletariat Butchery) on SE Foster | 4-8PM, Fresh Local Beef (more info)
• Canby: Swan Island Dahlia Festival | 9AM-5:30PM, 50 Acres of Blooms, Live Music, Food Trucks
• Cruise: Portland Spirit Cruises | Dinner, Champagne Brunch, Sightseeing & More!
• Cruise: 7 Wonders of the Gorge @ Portland Spirit | Jet Boat Cruise, Majestic Views. Runs Through September 27
• Dolly: Dolly Parton Day at The Pharmacy on NW 21st | 2PM-Close, Celebrate the legacy of the incomparable Dolly Parton. (more info)
• Drinks: Friday Happy Hour @ The Pharmacy on NW 21st Ave | 2-6PM, $7 Whiskey Sours (more info)
• Erotica: Erotica Open Mic @ Rose City Book Pub | 9-11PM, 21+, Free, Please bring your original erotic writing to share with an eager audience. (more info)
• Film: PEAKING: Psychedelics & The Pursuit of Happiness @ Cinema 21 | 4PM & 6:50PM, Portland Premiere, Live Q&A Following 6:50PM Screening
• Ghosts: Slabtown Tours presents A Night With Ghosts in NW Portland | 90 Minute Walking Tour, Local Paranormal History
• Happy Hour: Happy Hour Sightseeing Aboard The Portland Spirit | Boarding: 3PM, Cruising: 3:30PM – 5PM | See the city from a new perspective!
• Happy Hour: Food & Drink Specials at The Social Spoon in Downtown | 3-6PM, $2-6 Beer Selections, $6 Wells, $5 Wines, $10 Cocktails, Chili, Mac & Cheese, Salads, Pizza, Wings, Hot Dog, Cheeseburger, & more (more info)
• Happy Valley: Thurgood @ Adrienne C. Nelson High School in Happy Valley, OR |7:30PM,  One Man’s Fight to Change the Country
• Kelso: Cinema of Horrors Haunted House @ Three Rivers Crossing in Kelso, WA | 7-11PM, Portland Area’s #1 Haunted Attraction
• Music: Valkerie w/ Withholden, Laughing About Nothing, Fawkes Glove @ Mission Theater | 7PM, Alternative Rock
• Music: McMenamins Presents Jakki and the Pink Smudge w/ Ogre + Jonny’s Day Out @ Crystal Ballroom | Doors: 7PM, Show: 8PM, Indie Rock
• Oktoberfest: Oktoberfest Specials @ All McMenamins Locations | Food & Drink Specials Runs Through October 3rd
• Oysters: Oyster Social @ Négociant on NW 21st Ave | $2 Oysters from 2-4PM, Join them for a glass of wine, a special event or peruse the market (more info
• Theater: Agatha Christie’s ‘And Then There Were None’ @ Experience Theatre Project | 7:30PM,  Immersive Production of a Classic Mystery
• Tiki Cruise: Island Style Charters River Cruises | Happy Hour, City Views, Sunset Cruises, Tiki Night & City Lights, & More
• Titanic: Titanic: The Artifact Exhibition @ OMSI | 9:30AM-4PM, Real Artifacts Recovered from Titanic
• Wilsonville: Pumpkin Patch @ Frog Pond Farm | Llamas, Bounce House, Farm Animals & More
• Wine: Frosé Fridays at Hip Chicks Do Wine in SE | 4-7PM, 21+, Wine Slushies + Small Plates.(opens in new tab) Wine Flights and Wine by the glass available

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Portland Saturday Events, September 26:

• Bend: Oktoberfest @ Old St. Francis School | 1-9:30PM, Free, Live Music, Oktoberfest Lager, Food Specials 
• Bikes: Carry Sh*t Olympics – Portland, OR’s Underground Cargo Bike Racing Event | Free, Scavenger Hunt, Friday Night Ride, Cargo Polo, & more (more info)
• Burger: Butcher’s Burger at Meatstuff (formerly Proletariat Butchery) on SE Foster | 4-8PM, Fresh Local Beef (more info)
• Canby: Swan Island Dahlia Festival | 9AM-5:30PM, 50 Acres of Blooms, Live Music, Food Trucks
• Community: Mt. Tabor Park Volunteer Event | 9AM-1PM, Free, Help care for this special local park by removing weeds, maintaining trails, and more (more info)
• Cruise: Portland Spirit Cruises | Dinner, Brunch, Sightseeing & More!
• Cruise: Bigfoot Adventure Cruises @ Portland Spirit | Learn the History of Bigfoot on a Jet Boat
• Cruise: 7 Wonders of the Gorge @ Portland Spirit | Jet Boat Cruise, Majestic Views
• Ducks: Oregon Ducks at USC | 4:30PM, Where to Watch in Portland + Food & Drink Specials
• Expo: Oregon Pride in Business Rainbow Expo @ Social Good Place | 10AM-6PM, LGBTQIA2S+ Marketplace, Bites & Beverages, Community Resource Hall
• Festival: The Wedge @ Alder Block | 12-5PM, Taste 100s of Cheeses, Specialty Foods, Beer, Wine, Cider
• Film: Late Night Showing of Rocky Horror Picture Show @ Clinton Street Theater | 11PM, Weekly Screenings Since 1978 (more info)
• Film: PEAKING: Psychedelics & The Pursuit of Happiness @ Cinema 21 | 2PM, 4:30PM, 7:15PM, Portland Premiere, Live Q&A
• Forest: Lookout Landscape, an Immersive Forest-Art Exhibition @ World Forestry Center | 10AM-4PM, A new immersive art exhibition by David Buckley Borden and collaborators (more info)
• Ghosts: Slabtown Tours presents A Night With Ghosts in NW Portland | 90 Minute Walking Tour, Local Paranormal History
• Happy Hour: Happy Hour Sightseeing Aboard The Portland Spirit | Boarding: 3PM, Cruising: 3:30PM – 5PM | See the city from a new perspective!
• Happy Valley: Thurgood @ Adrienne C. Nelson High School in Happy Valley, OR | 7:30PM, One Man’s Fight to Change the Country
• Haunted: Haunted Corn Maze @ Bella Organic Farm | 6:30-10PM, Ghouls, Zombies, Costume Party
• Hillsboro: Oktoberfest @ Cornelius Pass Roadhouse | 6-9PM, Free, Live Music, Oktoberfest Lager, Food Specials 
• Kelso: Cinema of Horrors Haunted House @ Three Rivers Crossing in Kelso, WA | 7-11PM, Portland Area’s #1 Haunted Attraction
• Maze: Corn Maze ‘5 Kind Acts’ @ Bella Organic Farm on Sauvie Island | 9AM-5PM, Apple Cider, Trains, Petting Zoo & More
• McMinnville: Oktoberfest @ Hotel Oregon | 5-10PM, Free, Live Music, Oktoberfest Lager, Food Specials
• Mystery: Dinner Detective @ Embassy Suites | 6-8:30PM, Largest Murder Mystery Dinner Show in the US
• Pumpkins: Bella Organic Farm 15 Acre Pumpkin Patch on Sauvie Island | 9AM-6PM, Free Admission and Hay Rides, 50+ Varieties, Photo Opportunities
• Oktoberfest: Oktoberfest Brewfest @ McMenamins Kennedy School | 1-7PM, German Fare, Beer & Cider, Live Music
• Oktoberfest: Oktoberfest Specials @ All McMenamins Locations | Food & Drink Specials
• Oysters: Oyster Social @ Négociant on NW 21st Ave | $2 Oysters from 2-4PM, Join them for a glass of wine, a special event or peruse the market (more info)
• Owl: Woodsy Owl Birthday Party @ World Forestry Center | 10AM-12PM, Cupcakes, Woodsy Swag, Pop-Up Exhibit (more info)
• Sale: Chrome Industries Warehouse Sale in NW Portland | 10AM, Apparel, Messenger Bags, Slings & More
• Shrektember: Puss in Boots: The Last Wish at Clinton St Theater | 7PM, Shrektember Film Series (more info)
• St Helens: Spirit of Halloweentown in St. Helens, OR | 11AM-9PM, Oregon’s Must-Visit Halloween Festival
• Theater: Agatha Christie’s ‘And Then There Were None’ @ Experience Theatre Project | 2PM & 7:30PM, Immersive Production of a Classic Mystery
• Thorns: Portland Thorns vs Houston Dash @ Providence Park | 5:45PM, Where to Watch in Portland
• Thriller: Thrill the World Portland Dance Practice @ Irving Park’s Basketball Court | 11:30AM-1PM, World-Wide Thriller Dance
• Tiki Cruise: Island Style Charters River Cruises | Happy Hour, City Views, Sunset Cruises, Tiki Night & City Lights, & More
• Titanic: Titanic: The Artifact Exhibition @ OMSI | 9:30AM-6PM, Real Artifacts Recovered from Titanic
• Wilsonville: Pumpkin Patch @ Frog Pond Farm | Llamas, Bounce House, Farm Animals & More
• Wine: Hip Chicks Do Wine Open Weekends in SE Portland | 12-7PM, Local Discount, Tastings, Oldest Urban Winery in Portland

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Portland Sunday Events, September 27:

• Bikes: Carry Sh*t Olympics – Portland, OR’s Underground Cargo Bike Racing Event | Free, Scavenger Hunt, Friday Night Ride, Cargo Polo, & more (more info)
• Brunch: Portland Spirit Sunday Brunch Cruise | Bottomless Champagne & Mimosas, Live Music, Locally Sourced Cuisine (more info)
• Canby: Swan Island Dahlia Festival | 9AM-5:30PM, 50 Acres of Blooms, Live Music, Food Trucks
• Community: PDX Free Market at Albina Library | 12-4PM, Find free stuff and/or bring stuff you would otherwise donate (more info)
• Cruise: Portland Spirit Cruises | Dinner, Brunch, Sightseeing & More!
• Cruise: 7 Wonders of the Gorge @ Portland Spirit | Jet Boat Cruise, Majestic Views
• Film: PEAKING: Psychedelics & The Pursuit of Happiness @ Cinema 21 | 4:30PM, 7PM, Portland Premiere, Live Q&A
• Forest: Lookout Landscape, an Immersive Forest-Art Exhibition @ World Forestry Center | 10AM-4PM, A new immersive art exhibition by David Buckley Borden and collaborators (more info)
• Ghosts: Slabtown Tours presents A Night With Ghosts in NW Portland | 90 Minute Walking Tour, Local Paranormal History
• Happy Hour: Happy Hour Sightseeing Aboard The Portland Spirit | Boarding: 3PM, Cruising: 3:30PM – 5PM | See the city from a new perspective!
• Maze: Corn Maze ‘5 Kind Acts’ @ Bella Organic Farm on Sauvie Island | 9AM-5PM, Apple Cider, Trains, Petting Zoo & More
• Music: Kruder & Dorfmeister ‘K&D Kicks 30 Anniversary Tour’ @ Crystal Ballroom | 6:30PM, Nu Jazz, Trip Hop, Down Tempo
• Music: Kernside Serenade @ Rainbow Road (SE 28th & Ankeny) | 1-4PM, Kate Sweat, Aron Schur & Colin Ranney, Samie Jo (more info)
• Oktoberfest: Oktoberfest Specials @ All McMenamins Locations | Food & Drink Specials
• Oktoberfest: Oktoberfest & Plant Sale @ Edgefield | 11AM-7PM, Free, All Ages, Property-wide food specials, Face painting, Balloon artist, Live Music
• Oysters: Oyster Social @ Négociant on NW 21st Ave | $2 Oysters from 2-4PM, Join them for a glass of wine, a special event or peruse the market (more info)
• Promenade: Oregon Walks presents A Walk Across the City — The Portland Promenade | Free, Starts at 8:30am @ Luuwit View Park & Ends at Pioneer Courthouse Square (more info)
• Pumpkins: Bella Organic Farm 15 Acre Pumpkin Patch on Sauvie Island | 9AM-6PM, Free Admission and Hay Rides, 50+ Varieties, Photo Opportunities
• Sale: Chrome Industries Warehouse Sale in NW Portland | 10AM, Apparel, Messenger Bags, Slings & More
• Seahawks: Seattle Seahawks at Washington Commanders | 10AM, Week 3, Where to Watch in Portland + Food & Drink Specials
• St Helens: Spirit of Halloweentown in St. Helens, OR | 11AM-9PM, Oregon’s Must-Visit Halloween Festival
• Theater: Agatha Christie’s ‘And Then There Were None’ @ Experience Theatre Project | 1PM,  Immersive Production of a Classic Mystery
• Theater: Thurgood @ Adrienne C. Nelson High School in Happy Valley, OR | 2PM, One Man’s Fight to Change the Country
• Theater: Pride & Prejudice @ Portland Center Stage | 2PM & 7:30PM, A Bold New Comedic Take on a Beloved Classic
• Thriller: Thrill the World Portland Dance Practice @ Irving Park’s Basketball Court | 11:30AM-1PM, World-Wide Thriller Dance
• Tiki Cruise: Island Style Charters River Cruises | Happy Hour, City Views, Sunset Cruises, Tiki Night & City Lights, & More
• Titanic: Titanic: The Artifact Exhibition @ OMSI | 9:30AM-4PM, Real Artifacts Recovered from Titanic
• Trivia: Shanrock’s Triviology @ The Goodfoot | Full Bar, Food Menu, Pool
• Trivia: Free Portland Trivia w/ Bridgetown Trivia @ The Oaks Pub Pharmacy on SE Bybee in Sellwood | 6:30PM
• Wilsonville: Pumpkin Patch @ Frog Pond Farm | Llamas, Bounce House, Farm Animals & More
•  Wine: Hip Chicks Do Wine Open Weekends in SE Portland | 12-5PM, Local Discount, Tastings, Oldest Urban Winery in Portland

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Upcoming & Featured Portland Events:

• Next Week: Concerts, Comedy, Trivia, Theater, Happy Hours, & More!
• September: Our September Events Calendar + Giveaways
• GIVEAWAYS: Win Tickets to Concerts, Comedy, Festivals, Films, Theater, & More!
• Halloween: Events, Parties, Costume Contests, Haunts, Horror Films, Activities, & Giveaways!
• Jobs: Jobs Board – Creative, Tech, Construction, Green, Marketing, Service Industry, & More