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Friday - Monday

November 21st - January 1

Take The Train To Christmas Town


You now have an excuse to drive the family an hour east to board a train that transports travelers from the Columbia River Gorge’s foremost drinking town, through the winter wonderland of Mount Hood’s northern slope, and up to Parkdale. It’s the closest thing we’ll ever get to a Polar Express experience, only this one involves craft breweries at both ends of the journey if you so choose to include them. On second thought, maybe leave the kids behind.

Cost: $37-$65 for children 2-12, $47-85 for adults, depending on cabin selection



Friday - Saturday

November 24 - December 30

See The Lights At The Grotto


Though it’s technically a Catholic sanctuary that famously disallowed Portland Public Schools choirs from singing secular holiday songs during its annual Christmas Festival of Lights, it’s still a magical experience regardless of your religious affiliation or lack thereof. Just pretend you’re at a wedding and ignore the proceedings like you always do, right?

Cost: $6 for children 3-12, $10 for seniors 65+ and military, $11 for adults


Friday - Sunday

November 21- December 31

Travel South For Christmas In The Country


Head down to the Oregon Garden in Silverton for ice skating, artisanal holiday goods, Christmas karaoke and enough mulled wine and beer from Salem’s Gilgamesh Brewing to make it fun.

Cost: $3-$45 depending on activities


Friday - Tuesday

November 24 - December 26

Take A Drive In Winter Wonderland



December 16

Put On Your Santa Suit

Not quite as epic as it’s infamous NY-based brethren, Portland’s SantaCon is still one hell of a fine excuse to throw on a Santa suit, get tipsy and dance your weekend away at a handful of Pearl District and Old Town bars and clubs.

Cost: $10 (but bring more money for drinks)



December 17 

Celebrate Chanukah!

This free event for families with children aged 0-12 will surely get you in the festive spirit. It’s also a great opportunity to learn how to create a menorah, make sufganiyot, or how to play dreidel. There will be dancing and singing, story time, and a play area.


December 12 - 19

Menorah Lighting

Want to observe the holiday in an expedient manner? You’ll easily make it home in time for dinner and baby bedtimes with Chabad of Oregon’s five minute menorah lighting at Director Park. This free event, now in it’s 34th year, takes place every night December 12 through 19 from exactly 5:30-5:35 pm. Want to celebrate a little longer? Join the First Night Celebration, which features music, food and children’s crafts from 4:30-6 pm.



December 31

Where To Ring In The New Year

2018 New Year’s Eve Celebration @ Bare Bones Cafe! | No Cover & Free Champagne Toast at Midnight!

DJ Anjali & The Incredible Kid’s 2018 New Year’s Eve Dance Party Extravaganza @ Melody Ballroom | w/ Orquestra Pacifico Tropical, Savila & Dholi

Portland New Year’s Eve 2017-2018 Celebration w/ The Motet @ Revolution Hall | 7-Piece Funk Powerhouse, The Future of Funk, Soul (Win Tickets, $80+)

New Year’s Eve w/ Fruition & The Lil’ Smokies @ Crystal Ballroom | Champagne Toast, Soul, Blues, British Invasion, Bluegrass, Stringband (Win Tickets, $70)

Midnite New Year’s Eve @ Pure Space in Portland’s Pearl District | Featuring SKAM Artist DJs Fergie DJ, DJ Christyle, Light Show, Projection Clock & More!

New Year’s Eve 2018 @ Dig A Pony DJ – Dance Hard, Kiss Soft NYE w/ Maxx Bass, Lamar & Special Guests

Ring in 2018 at Portland’s Most Famous New Year’s Eve Party Champagne Ball in Downtown! | 17 Bars, 3 Dance Floors, Black Tie, Toast & Count

Holiday Tea @ Pix Patisserie | Formal & Fun, All Inclusive Menu, Sweet & Savory Snacks

Celebrate 2018 w/ Pix Patisserie’s New Year’s Eve Extravaganza Chocolate Buffet | Mousse, Cake, Meringue, Beer & More!

Barrel Room Presents Old Town Portland’s Largest New Year’s Eve 2018 Celebration! | Champagne Toast, Two Stages, DJs, Dueling Pianos w/ Liz Fohl and Steven Ramirez

Tony’s AM Gold Seventies Soft Rockin’ 2017 / 2018 Portland New Years Eve @ Tony Starlight Showroom | Featuring Hits from Elton John, Neil Diamond, Carol King & More!

Cruise into 2018 w/ Portland Spirit’s New Year’s Eve Party! | Champagne Toast, Live Music w/ The Bylines & The Doc Watson Jazz Trio, Snacks & More!

New Years Eve Celebration @ Goodfoot Pub & Lounge | The Quick & Easy Boys (downstairs), Soul Stew DJs (upstairs)

The Dinner Detective in Downtown Portland | Largest Murder Mystery Dinner Show In The U.S., Saturdays, Everyone’s Suspect