MANY Portland Christmas Weekend Events & Giveaways ($1,200+): Holiday Markets, Cinnamon Bear, Gift Ideas & More! | December 22-25, 2022

Christmas weekend is here, Portland! Find your last-minute gifts at Winter Fair & Holiday Market or at PDX Urban Wineries Holiday Pop Up. There’s still time to see Christmas at The Old Church. And New Year’s Eve is coming up, enter to win tickets to ring in 2023.

Featured: Portland New Years Eve 2022 – Parties to Get 2023 Started

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Win Portland Tickets

Win Tickets ($60): Yak Attack New Year’s Eve 2022/2023 @ The Gooodfoot Pub & Lounge Downstairs | Organic Electronica, Jam, Funk, Jazz (Dec 31)
Win Tickets ($60): The EYE BALL! A New Year’s Eve Surrealist’s Dance Party @ Polaris Hall in NE Portland | Champagne Toast, w/ Sun Atoms, DJs Rescue & Gregarious (Dec 31)
Win Tickets ($80): New Year’s Eve 2023 w/ Digable Planets @ Crystal Ballroom in Downtown Portland | Jazz-informed Hip Hop (Dec 31)
Win Tickets ($50): The Bridgetown Boogie 2023 New Year’s Eve @ Aladdin Theater | Featuring Polyrhythmics w/ Adryon de León (Dec 31)
Win Tickets ($50): New Year’s Eve w/ Soul Stew Featuring DJ Aquaman and Friends Upstairs @ The Goodfoot Pub & Lounge | Funk, Soul, Disco (Dec 31)
Win Tickets ($70): Unrealistic Work Goals @ Clinton Street Theater | Conversation About How to Create Stronger Work Boundaries (Jan 8)
Win Tickets ($30): dKOTA Album Release @ The Old Church Concert Hall | w/ Pulp Western (Jan 13)
Win Tickets ($80): Portland Folk Festival @ Crystal Ballroom | Ron Artis II, Hillstomp, Rayland Baxter, Fox and Bones & More! (Jan 14)
Win Tickets ($34): Gill Landry (of Old Crow Medicine Show) @ The Old Church Concert Hall | 2-Time Grammy Award Winning Singer/songwriter (Jan 21)
Win Tickets ($60): Super Diamond @ Crystal Ballroom | Neil Diamond Tribute (Jan 28)
Win Tickets ($36): Gilla Band @ Mission Theater | Irish Post Punk, Noise Rock (Feb 13)
Win Tickets ($90): The Charlatans UK, Ride @ Crystal Ballroom | English Rock (Feb 15)
Win Tickets ($100): Oregon Distilled Craft Spirits Festival 2023 @ The Redd | 30+ Distillers, 120+ Different Spirits, Fine Food & more! (Feb 18)
Win Tickets ($50): Magic City Hippies @ Crystal Ballroom | w/ CAPYAC, Psychedelic Funk (Feb 19)
Win Tickets ($70): Yonder Mountain String Band @ Crystal Ballroom | Jam-grass (March 25)
Win Tickets ($80): Aly & AJ @ Crystal Ballroom | Pop Rock Duo, Indie (April 1)
Win Tickets ($60): Steel Panther, Crobot, Tragedy @ Crystal Ballroom | Comedic Glam Metal (April 4)
Win Tickets ($50): Rome Streetz @ Lola’s Room | Hip Hop, A Mix of Gritty New York Boom Bap & London Grime (April 11)
Win Tickets ($60): An Evening with Lotus @ Crystal Ballroom | Instrumental Electronic Jam Band (April 24)

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Portland Thursday Events, December 22

NOTE: Due to weather, events might be canceled or changed. Please check for updates w/ event organizers

Cruise: Portland Spirit Sightseeing Cruises Through the Heart of Downtown Portland | Lunch, Dinner, Brunch
Drinks: $7 Margarita Thursday @ The EastBurn Public House | 8AM-11PM, Inside Dining, Heated Patio, Sidewalk Cafe (more info)
Film: The Big Lebowski @ Clinton Street Theater | 7PM (more info)
Happy Hour: Stem Wine Bar Happy Hour | 5-7PM, $2 Off Glasses, $5 off Bottles (more info)
Happy Hour: Happy Hour at The Pharmacy (NW 21st) | 2-6PM, Drink Specials, Sliders, Pita & Hummus, Quesadillas, Pretzels, & more! (more info)
Holidays: A Very Merry PDX-mas @ Broadway Rose New Stage | Classic Carols, Holiday Pop Songs & Original Offbeat Material
Holidays: Hayley Lynn @ Nike for Holidays on the Mall in Downtown Portland | Noon-1PM (more info)
Holidays: Jennifer O’Leary Holiday Performance @ Pioneer Courthouse Square | Noon-1PM (more info)
Holidays: Jordan Sings @ MUJI – Holidays on the Mall in Downtown Portland | 5-6PM (more info)
Holidays: Peacock Lane Free Holiday Display in SE Portland
Holidays: Lightopia – An Illuminated Journey @ Hillsboro Stadium | Free Drive-through Light Up Attraction, Reservations Required (more info)
Holidays: NE Alberta Street Presents Gnome for the Holidays | Scavenger Hunt, Raffle (more info)
Holidays: Winter Fair & Holiday Market @ Clackamas County Event Center | 25+ Vendors, Santa, Treats, Gifts, 200 Thousand Lights & More!
Holidays: Portland Spirit Cinnamon Bear Holiday Breakfast Cruises in Downtown Portland | Storytelling, Music, Magic
Holidays: PDX Urban Wineries Holiday Pop Up @ Director Park in Downtown Portland | Featuring 14 Member Wineries, Mix & Match Tastings, Discounts
Music: On One Posse Electro-Boogie Dance Party @ The Goodfoot Pub & Lounge | 9PM, Vinyl-based Dance Party (more info)
Music: Robby Hoffman @ Mississippi Studios | 9PM, w/ Simon Gibson (more info)
Music: Free Live Music @ Cooper Mountain Ale Works Public House in Tigard | Featuring Eric John Kaiser
Roller Skating: Secret Roller Disco | 7-9PM, Free (more info)
Scavenger Hunt: Urban Adventure Quest’s Amazing Scavenger Hunt Adventure! | Discover Portland’s Hidden Mysteries + Discount / Promo Code
Trivia: ShanRock’s Triviology Presents Thursday Trivia @ BareBones | 7PM, Prizes
Trivia: ShanRock’s Triviology Presents Thursday Trivia @ The EastBurn Public House | 7PM, Prizes
Wine: ENSO Winery Open in SE Portland | Flights, Glasses, Light Food Menu, Indoor & Outdoor Seating
Wine: Boedecker Cellars Winery, Tasting Room & Bottle Shop Now Open in NW Portland | Reservations, Huge Outdoor Space, Delivery

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Portland Friday Events, December 23

NOTE: Due to weather, events might be canceled or changed. Please check for updates w/ event organizers

Blazers: Portland Trail Blazers vs Denver | 6PM, Where to Watch in Portland
Dining: Friday Soup Night @ Boedecker Cellars | Soup & Wine Pairing, Special Bottle Pricing
DJ: DJ Vinnie Tomatoes @ The Pharmacy (NW 21st) | 9:30PM (more info)
DJ: Soul Stew Featuring DJ Aquaman and Friends @ The Goodfoot Pub & Lounge | 9PM, Funk, Soul, Disco (more info)
Drinks: Old Fashion Fridays @ The EastBurn Public House | 8AM-11PM, Inside Dining, Heated Patio, Sidewalk Cafe (more info)
Happy Hour: Happy Hour at The Pharmacy (NW 21st) | 2-6PM, Drink Specials, Sliders, Pita & Hummus, Quesadillas, Pretzels, & more! (more info)
Holidays: Peacock Lane Free Holiday Display in SE Portland
Holidays: Lightopia – An Illuminated Journey @ Hillsboro Stadium | Free Drive-through Light Up Attraction, Reservations Required (more info)
Holidays: NE Alberta Street Presents Gnome for the Holidays | Scavenger Hunt, Raffle (more info)
Holidays: LaRhonda Steele @ Holidays on the Mall in Downtown Portland | Noon-1PM (more info)
Holidays: The Blueprint Carolers Holiday Performance @ Pioneer Courthouse Square | Noon-1PM (more info)
Holidays: Over The Bridge Jazz Holiday Performance @ Pioneer Courthouse Square | 5-6PM (more info)
Holidays: Winter Fair & Holiday Market @ Clackamas County Event Center | 25+ Vendors, Santa, Treats, Gifts, 200 Thousand Lights & More!
Holidays: PDX Urban Wineries Holiday Pop Up @ Director Park in Downtown Portland | Featuring 14 Member Wineries, Mix & Match Tastings, Discounts
Music: Mississippi Studios presents Jangly Balls @ Bar Bar | 9PM, w/ Montel Spinozza and Cee White (more info)
Scavenger Hunt: Urban Adventure Quest’s Amazing Scavenger Hunt Adventure! | Discover Portland’s Hidden Mysteries + Discount / Promo Code
Wine: Stem Wine Bar Serving Up Extensive Wine Selection & Flights in North Portland | Patio, Live Music, Trivia
Wine: ENSO Winery Open in SE Portland | Flights, Glasses, Light Food Menu, Indoor & Outdoor Seating
Wine: Wine: Hip Chicks Do Wine Open Weekends in SE Portland | Tastings, Oldest Urban Winery in Portland

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Portland Saturday Events, December 24

NOTE: Due to weather, events might be canceled or changed. Please check for updates w/ event organizers

Brunch: Weekend Brunch @ The EastBurn Public House | Mimosa Flights, Bloody Marys
Cruise: Portland Spirit Sightseeing Cruises Through the Heart of Downtown Portland | Lunch, Dinner, Brunch
DJ: DJ Bil @ The Pharmacy (NW 21st) | 9:30PM (more info)
Drinks: Goodfoot Pub & Lounge Upstairs Open Christmas Eve | 8PM, Drinks, Pool, Art (more info)
Drinks: $7 Bulleit or Ketel One Mules @ The EastBurn Public House | 5-11PM, Inside Dining, Heated Patio, Sidewalk Cafe (more info)
Film: Rocky Horror Picture Show Midnight Showing @ Clinton Street Theater | 11:59PM (more info)
Film: The Big Lebowski @ Clinton Street Theater | 3PM & 7PM (more info)
Holidays: Peacock Lane Free Holiday Display in SE Portland
Holidays: Christmas at The Old Church with Michael Allen Harrison in Downtown Portland | Beloved Holiday Tradition, w/ Gospel, Blues & Jazz Singer Julianne Johnson
Holidays: Lightopia – An Illuminated Journey @ Hillsboro Stadium | Free Drive-through Light Up Attraction, Reservations Required (more info)
Holidays: NE Alberta Street Presents Gnome for the Holidays | Scavenger Hunt, Raffle (more info)
Holidays: Portland Spirit Cinnamon Bear Holiday Breakfast Cruises in Downtown Portland | Storytelling, Music, Magic
Holidays: PDX Urban Wineries Holiday Pop Up @ Director Park in Downtown Portland | Featuring 14 Member Wineries, Mix & Match Tastings, Discounts
Scavenger Hunt: Urban Adventure Quest’s Amazing Scavenger Hunt Adventure! | Discover Portland’s Hidden Mysteries + Discount / Promo Code
Wine: Stem Wine Bar Serving Up Extensive Wine Selection & Flights in North Portland | Patio, Live Music, Trivia
Wine: Wine: Hip Chicks Do Wine Open Weekends in SE Portland | Tastings, Oldest Urban Winery in Portland

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Portland Christmas Day Events, December 25

Drinks: Upstairs Open @ The Goodfoot Pub & Lounge | 8PM, Food & Drink Specials (more info)
Holidays: Peacock Lane Free Holiday Display in SE Portland
Holidays: Lightopia – An Illuminated Journey @ Hillsboro Stadium | Free Drive-through Light Up Attraction, Reservations Required (more info)
Holidays: NE Alberta Street Presents Gnome for the Holidays | Scavenger Hunt, Raffle (more info)
Holidays: Potluck in the Park @ Portland Art Museum | Noon-3PM, Free Christmas Dinner (more info)
Holidays: Portland Spirit Christmas Day Buffet Cruise | Holiday Classics, Beautiful City Views
Scavenger Hunt: Urban Adventure Quest’s Amazing Scavenger Hunt Adventure! | Discover Portland’s Hidden Mysteries + Discount / Promo Code