A round up of what’s going on in Portland this week including festivals, concerts, comedy, trivia, happy hours, movies, & more!
2025 Portland Halloween @ McMenamins: Kennedy School, Cornelius Pass Roadhouse, Grand Lodge, White Eagle, Edgefield, Grand Lodge
Spooky season is finally here! Whether you’re planning a night of fun and treats, ghoulish tricks or something in between, McMenamins is ready with Halloween parties and more this month.
Wine Wednesdays @ Négociant | Weekly Wine Flights & Tastings
Wine Wednesday is now in its third year and has become a staple in our weekly routine and part of the tradition around here.
Cappella Romana presents Mass Appeal w/ Portland Youth Philharmonic @ St. Mary’s Cathedral | Stravinsky + Bruckner
Brace yourself for a sonic experience that stirs the soul and lifts the roof.
Win Tickets ($52): Rory Scovel: Know Your Enemy Tour (Late Show) @ Aladdin Theater | Comedian & Actor from ‘Physical’
Rory Scovel is an actor, comedian, and writer. His latest comedy special RORY SCOVEL: RELIGION, SEX, AND A FEW THINGS IN BETWEEN released in February, 2024 on Max.
The Great Pumpkin Run @ Springwater Corridor Trail | Halloween Costumes, Candy & More
Get ready to dress up, run in your favorite Halloween costume & snag candy at aid stations on course
Growl & Wail @ Deep End Theater | Improvised Horror Play
We love this season at Deep End Theater and we are delighted to be bringing back one of our favorite spooky shows!
Albariza Wine Bar Social @ Meatstuff/Proletariat Butchery | Charred Meaty Bones, Caviar Bumps, Fancy Cheese & More
A once a month casual good time spent mingling, drinking good wine and grazing on (sometimes unusual) meaty things at a butcher shop.
Win Tickets ($100): Sam Bush @ Aladdin Theater | Progressive Bluegrass Mandolinist
There is only one consensus pick of peers and predecessors, of the traditionalists, the rebels, and the next gen devotees. Music’s ultimate inside outsider. Or is it outside insider? There is only one Sam Bush.
Rise Up Northwest in Unity Convening @ Portland Expo Center | Safeguarding the Northwest’s Essential Life Sources
The third annual Rise Up Northwest in Unity Convening (R.U.N.) is coming to Portland!
Win Tickets ($100): Pete Correale: As I Was Saying @ Aladdin Theater | The Pete and Sebastian Show
Pete has performed on numerous late night tv shows such as The Tonight Show, Letterman and Conan as well as filming three of his own one hour television comedy specials.
The Journey Within: Meditation & Wisdom @ Oregon Convention Center | Gurudev Sri Sri Ravi Shankar
World-renowned meditation master and peace ambassador Gurudev Sri Sri Ravi Shankar will be arriving in Portland, Oregon, with The Journey Within—a unique pathway to profound peace and personal growth.
“A Scary Home Companion” @ Victorian Belle | Live Radio Stage Dinner & Show
Summoned from the deepest, darkest pits of Hell and doomed to roam the earth for eternity (or at least six seasons per demonic contract), comes Portland’s own creepy and comical live radio stage show– Scary Home Companion!
Win Tickets ($64): Oliver Hazard & The Last Revel: Head West @ Aladdin Theater | Folk, Country
Much like their sorrowful, purposeful melodies, the members of The Last Revel contain this thick thread of self, and of place.
FREE Improv Workshop @ Deep End Theater | | Led by Domeka Parker
Join us for a fun afternoon of play! In this workshop we will dip our toes into Deep End’s unique improv style.
The Belle Supper Club @ Victorian Belle | A Haunted Disco Burlesque Dinner Cabaret
Join us at Portland’s most charmingly titillating vintage dinner experience in the city at THE BELLE SUPPER CLUB!
Win Tickets ($36): Fox & Bones w/ Wood Butcher & Justin Farren @ Showdown Saloon | Rocky-Folk/Psych-Rock
Scott Gilmore and Sarah Vitort are Fox and Bones—energetic offbeat folksters with a retro-tinged, soul-stirring, modern vintage bent.
Literary Arts presents Timothy Snyder in Conversation @ Arlene Schnitzer Concert Hall | Bestselling Author of ‘On Tyranny’
Literary Arts is thrilled to present Timothy Snyder, bestselling author of On Tyranny.
Win Tickets ($56): Little Cloud Records Showcase @ Mission Theater | Magic Castles, Pete International Airport, Flavor Crystals & Pink Breath of Heaven
Magic Castles are a neo-psychedelic band from Minneapolis MN, formed in the late 2000s by multi-instrumentalist and songwriter Jason Edmonds.
Win Tickets ($30): Patterns Fly @ The Goodfoot | Funk, Psychedelic, Jazz
Seattle based guitarist Andy Coe (ACB, Skerik Band, McTuff) and drummer D’Vonne Lewis (Digable Planets, McTuff, Industrial Revelation) join forces with Portland keyboardist Galen Clark
Win Tickets ($70): Aaron Golay & The Original Sin @ Mission Theater | Americana, Roots, Soul
Loud, yet tender with high energy, engaging live performances are what stand out with Aaron Golay & The Original Sin.
Win Tickets ($48): Mexican Slum Rats @ Mission Theater | Alternative, Indie
Five-piece alternative band hailing from Granada Hills, CA. The five create an atmosphere that is overwhelming with emotion.
Neil Diamond Experience w/ Tony Starlight @ Alberta Rose Theatre | 7-Piece Band Neil Diamond Tribute
Musical comedian Tony Starlight shall Neil before you! Starlight fronts a seven-piece band that performs a loving tribute to Neil Diamond with equal parts heart and laughter.
Portland in the News: Emergency World Naked Bike Ride, Park Meter Extension Cancelled, America’s Best Restaurants & More | October 2, 2025
After Trump announced plans to deploy the National Guard in Portland, an offshoot of the World Naked Bike Ride group announced plans for an emergency naked bike ride in protest of the occupation.
A Nightmare on Clinton Street | A Month of Horror Movies & Cocktails @ Clinton Street Theater & Dots Cafe
As long as Clinton Street Theater keeps rolling out a month of killer programming, we are going to keep throwing up a month of cocktails to go along with it.
2025 October Fruit Loop Events in Hood River & Parkdale | Fiesta Days, U-Pick Apples, Cider Days & More
Choices and more choices! Amazing u-pick selection of apples, pears, peaches, nectarines and raspberries.
2025 Halloween VHS Swap & Vendor Market @ Dots Cafe | Halloween Goods, DJ Rob Drokker
We figured what’s the point in having a Halloween market at the end of the month, when you can come get all your Halloween goods early.
World Forestry Center presents Forest Pub @ Mission Theater | Spooky Forest Tree Lore
👻 Join us this October for a hauntingly fun edition of Forest Pub! Cozy up with a drink and dive into the eerie side of forest folk stories.
2025 Sitka Art Invitational Show & Sale @ Oregon Contemporary | 100 Local Artists + 300 Works of Art
The Sitka Art Invitational show and sale—the Northwest’s largest and longest-running art event —is happening October 10-12, 11am-5pm.
Portland Spirit Presents 2025 Boo Cruise | Halloween Costume Contest, DJ, Multiple Floors
Get on board for a ghoulishly good time on our Halloween Boo Cruise!
2025 Halloween @ Escapism | Ritual Room Escape Room Gets Halloween Makeover
Explore the classic Ritual Room puzzles with all new spooky lighting and decor for a limited time!
Win Tickets ($30): Jujuba @ The Goodfoot | Nigerian Afrobeat
Jujuba delivers a funky, danceable style of Nigerian Afrobeat and Juju music.
Wine & Design: Harvest Broom Class @ Hip Chicks Do Wine | Decorate Your Own Harvest Broom + Wine
In this session, of our Wine & Design series, instructor Laura Gifford Kerr, Gifford’s Flowers will guide you in decorating your very own harvest broom.
2025 Hawthorne Ghost Tours | Family-friendly Haunted Adventure
The Hawthorne Ghost Tour is a fun, exciting, and family friendly adventure through the heart of East Portland’s most haunted street.
Win Tickets ($30): One Way Out @ The Goodfoot | Allman Brothers Tribute
One Way Out is a powerhouse 8 piece Allman Brothers Band tribute with a growing reputation for fiery live performances that capture peak ABB magic!
White Bird Presents Limón Dance Company at Arlene Schnitzer Concert Hall
Limón Dance Company—one of America’s most iconic modern dance ensembles—brings its signature power and emotion to Portland.
Win Tickets ($84): Bella Organic Presents ‘Human Rights for All’ Corn Maze & Pumpkin Patch | Haunted Maze, Petting Zoo, Food & Drinks
This fall, get lost in our 7-acre corn maze on Sauvie Island.
THIS WEEK in Portland: Festivals, Music, Comedy, Trivia, Theater, Happy Hours, & More!
| Today
2026 Swan Island Dahlia Festival | 50 Acres of Blooms, Food Carts, Live Music
| All Ages, events, Food & Drink, music
7 Deadly Sins Pants On Fire Family Friendly Show @ White Eagle Saloon | Seven True Tales, One Lie
| All Ages, Comedy, north portland, theater
Win Tickets ($130): Portland Weird Fest @ Oaks Park | 60+ Vendors, Rides, Live Bands, Costume Contest & More
| All Ages, Food & Drink, music, SE Portland, Shopping
Win Tickets ($136): Dogstar w/ The Backfires @ Crystal Ballroom | Keanu Reeves, Alt-Rock
| All Ages, downtown, events, music
Win Tickets ($92): Marc Price @ Mission Theater | Comedy, Star of ‘Trick or Treat’, ‘Family Ties’
| Comedy, NW Portland
Win Tickets ($22): Decadent 80s w/ DJ NoN @ Crystal Ballroom | Portland’s Longest Running 80s Night
| downtown, events, music
2026 Cannon Beach Cottage Tour | Self-Guided Walking Tour of Beautiful Homes, Opening Night Bash
| All Ages, events, Visual Art
2026 Time-Based Art Festival @ Portland Institute for Contemporary Art | Experimental Performances, Live Music, Dance & More
| Dance, events, Film, Food & Drink, music, NE Portland, theater, Visual Art
Lake Oswego Clean Energy and EV Fair @ Lake Oswego United Methodist Church | Test Drive EVs, Learn About Solar, Batteries & More
| All Ages, events, Home Show, Services, Shopping
Win Tickets ($42): Valkerie w/ Withholden, Laughing About Nothing, Fawkes Glove @ Mission Theater | Alternative Rock
| All Ages, music, NW Portland
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