Grab your cocoa, turn on Portland's Christmas Station and get out and make some new holiday memories!

The Gingerbread Masterpiece at The Benson Hotel is on display now through January 4. For 54 years the historic Portland hotel makes a special gingerbread creation the centerpiece of its lobby. This year, they display a castle inspired by The Royal Palace of Oz, from Wicked and the Wizard of Oz.

Free pet photos with Santa at PetSmart are happening Dec 13 & 14 from 2-5 p.m.. Photos can be taken on personal device or on store device, which will deliver the photo to you via email.

Time for your Pictures With Santa! Kick off the season at Washington Square and keep listening for Stacey & Mike's 12 Days of Christmas to win a $200 gift certificate to your favorite Washington Square stores like Lululemon, Dick's Sporting Goods and Aritzia thanks our friends at Explore Tualatin Valley. On select days (sign up here) you can get your very Portlandesque Santa Pic with Hipster Santa! You can also find Santa (thanks to that magic North Pole pixie dust) swooping into Evergreen Aviation & Space Museum by helicopter on Saturday December 13 at noon.

The Winter Village in Hillsboro offers covered outdoor ice skating at Jerry Willey Plaza at Orenco Station through January 11, 2026. Public skate sessions will be open Thursdays through Sundays.

Crafty Wonderland is the ultimate local handmade art and craft event of the season. Crafty Wonderland is taking over the Oregon Convention Center this weekend. More than 300 local artists feature fun, creative and one-of-a-kind goods. This event attracts popular local artists, creators and purveyors.

There's nothing like the smell of a real tree in the house. Bundle up and go find yours at Topaz Farms on Sauvie Island. They transform into a miniature Winter Wonderland on select dates. All trees are freshly cut and pre-shaken.

The Holiday Express is back in SW Portland. Join Santa Claus and his elves for a magical ride behind the 1912 Polson #2 steam locomotive. Decorated in festive cheer, the heated vintage rail cars transport you along the Willamette River in the heart of the city.

The Polar Express Train Ride is such a fun family tradition on the Mt. Hood Railroad. Stacey and her boys went numerous years, dressed in pj's singing along to the soundtrack, sippin' cocoa and meeting Santa! It runs on select days now through early January.

ICE SKATING

Lloyd Center Ice Rink keeps tradition alive with daily sessions and DJ nights.

OMSI on Ice offers indoor skating through December 31.

Hillsboro’s Winter Village transforms Jerry Willey Plaza into a festive rink through January 11.

Beaverton’s Winterhawks Skating Center lets you skate where the pros practice.

Vancouver’s Mountain View Ice Arena and Sherwood Ice Arena round out the list with daily public sessions.

LIGHT DISPLAYS:

Oregon Zoo Lights has some new additions this season. Including 30 more luminous creatures are joining the regular cast of glowing wildlife and lanterns along the train route, including flamingos, beavers, bears and elephants. The Zoo is also hosting its first 21+ night when grown-ups get to take in the holiday magic without kids on Saturday, Jan. 3.

Silverton Christmas Market Nov 21st - New Years Eve at The Oregon Garden Garden has 1.5 million lights. They have a Biergarten, snowless Tubing Hill and local artisan vendors. Santa will also be popping by between his toy making and eating cookies.

The Grotto Christmas Festival of Lights. Millions of lights across the sanctuary grounds. Opening November 28. If you can, bring a non-perishable food item for Snow Cap.

The 71st season of The Christmas Ships Parades on the Columbia River and Monday December 9th on the Willamette River. Over 70 beautifully decorated and illuminated boats will parade 15 nights during December. Weeknight parades launch from Riverplace Marina on the Willamette and the Gleason Boat Ramp on the Columbia. Some riverside restaurants book out early on Christmas Ship nights.

A new holiday festival is going on in Keizer at the former Volcanoes Stadium, now Roto Rooter Park, is home to Glow Oregon. Over 1 million lights, and a ton of activities for the littles with a reindeer garden, teddy bear village, fairytale castle, even a scavenger hunt for presents.

Peacock Lane is untangling millions of lights (better them than us!) so give them a minute. A Portland tradition for over 100 years, the annual Christmas Street opens Dec 15. Car-free nights (walkers only) are Dec. 19-20.

The Home For The Holidays Decades Tour at Pittock Mansion. Enjoy festive displays across 19 rooms in the mansion and four in the Gate Lodge, each artfully decorated to reflect a nesting of five iconic decades — from the 1910s through the 1950s. It’ll run thru January 9th.

PIR Winter Wonderland boasts 250 colorful light set pieces and many fully animated scenes. All proceeds benefit the Sunshine Division, which provides food for residents in need. This year there will again be car-free nights including Bike the Lights on Nov. 30, and Lights & Leashes on Dec. 1-2.

Magic At The Mill in Salem The Willamette Heritage Center offers a weekend of living history demonstrations, museum tours, Santa visits, children’s activities, craft demos, model trains, vendors and, of course, evening outdoor light displays.

Tigard Holiday Lights Walk is Saturday Dec 13. This homegrown event highlights beautifully lighted homes along a planned route. See the neighborhood transform into a glowing winter wonderland. Take a stroll through the light route on foot or hop in the car and crank the the holiday tunes.

Lightopia in Hillsboro offers a whimsical drive-through experience with giant glowing characters, tunnels of color, and synchronized music. For 2025, the event runs December 9 through December 29, open Fridays through Mondays from 5 p.m. to 9 p.m. at the Gordon Faber Recreation Complex.

Ready to see dazzling lights nestled in a Washington forest? Take a drive to Skamania Lodge for the second annual Holiday Light Walk. It runs from November 28th through January 4th. From 5-9 p.m. every night.

DOWNTOWN PORTLAND:

Pride Northwest is putting on our their Powerfully Pink holiday celebration again this year including events like Melodies in Midtown Friday Dec 6th at the Midtown Beer Gardens and culminating in a two-day night market, Bigger Picture, on December 13 and 14. The Pop Up Gallery will be at 23 NW 4th Ave. The mission is to amplify voices, spark collaboration, and create an accessible space where every artist - of every medium - can be seen, heard, and celebrated. Our mission: to uplift local creators, inspire connection, and remind the world that art lives everywhere and in everyone.

The PDX Pop-Up Shops are back! These beloved pop-up shops transform vacant retail spaces in downtown Portland into vibrant, temporary destinations for local designers and artists.

The Great Figgy Pudding Caroling Competition, Dec 12th at Pioneer Courthouse Square, has groups of carolers filling the streets of downtown Portland.

The Annual Tuba Christmas is a festive favorite for 34 years now. Dec 13th experience the mighty sounds of big brass as nearly 300 tubas play in harmony while the crowd is invited to sing along.

A uniquely Portland holiday tradition, the Cinnamon Bear Cruises aboard the Portland Spirit are now in their 20th year, introducing new generations to the holiday story that began as a Portland radio program in 1937.

Ready to see dazzling lights nestled in a Washington forest? Take a drive to Skamania Lodge for the second annual Holiday Light Walk. During the holiday season, the lodge hosts a variety of events. From November 28, 2025, through January 4, 2026, attend the Skamania Lodge Holiday Light Walk. From 5-9 p.m. every night, you can walk through their lights and displays surrounded by towering trees in a Pacific Northwest forest.

VANCOUVER EVENTS:

Vancouver shines bright each winter with festive events, dazzling lights, and holiday cheer along the Columbia River. From waterfront parades and historic downtown celebrations to artisan markets and beloved performances, there’s no shortage of Christmas events and winter activities to enjoy.

Heritage Holiday at Fort Vancouver - Experience the joy of the season in a historic setting with lots of festivities for families Dec 13.

Christmas Ships Parade - Watch a sparkling fleet of decorated boats sail along the Columbia River in this beloved Northwest holiday tradition.

Santa’s Holiday Hustle 5K - Get moving this holiday season with a festive run (or walk) perfect for the whole family—holiday attire encouraged!

Ice Skating & Winter Activities - Lace up your skates at an ice skating rink or take in winter hikes and scenic parks.

HOLIDAY CONCERTS:

“A Very George Michael Christmas,” Saturday Dec 20 at Alberta Rose Theater. A holiday-themed concert featuring music from the beloved Wham! singer by tribute band The Careless Whispers, led by Portland artist Holcombe Waller.

The Annual Tuba Christmas is Dec 13th at Pioneer Courthouse Square. A festive favorite for 34 years now. Dec 13th experience the mighty sounds of big brass as nearly 300 tubas play in harmony while the crowd is invited to sing along.

White Album Xmas is a “holiday circus spectacular” at the Alberta Rose Theatre Nov 28-Dec 13. A tribute to The Beatles, featuring music from The NowHere Band and performances by the Rose City Circus.

The Oregon Symphony plays all the popular holiday hits in “Holiday Pops” at the Arlene Schnitzer Concert Hall Dec 13 & 14. The show is billed as a perfect family activity or holiday date night.

Portland musician Michael Allen Harrison is known for his Christmas concerts at The Old Church featuring gospel, blues and jazz singer Julianne Johnson. Dec 13 - Christmas Eve.

NEW YEARS EVE:

If you're going out for New Years, Go by Trimet.

PBOT is hoping you’ll take their discount code and use a ride share service. For the second year in a row they're offering $10 off both Uber and Lyft on New Year's Eve. Just download a coupon from the Safe Ride Home website.

Portland’s Pioneer Courthouse Square will have a drone show while hits of the ’80s and beyond play. The party begins at 8 p.m., and the family-friendly drone display countdown starts at 9 p.m. For the adults, the countdown to the new year, and the second drone show of the evening, begins at midnight, and the event will conclude at 12:30 a.m.

Dance the year away at Revolution Hall with DJ Anjali and The Incredible Kid.

Cowboy Disco Ball New Year’s Eve Bash at McMemamin's Kennedy School.

If you're feelin fancy the party at Ritz Carlton downtown Portland features a cocktail reception, a four-course dinner by Chef Pedro Almeida, festive libations flowing all night, and a midnight toast to ring in the new year.

Bing in the New Year: A Milwaukie Celebration of the Bing Cherry Legacy on Wednesday, December 31 from 6–9 p.m. in downtown Milwaukie. This free community celebration features Chinese dancing, drumming, lion dancers, food vendors, live music, and a beer garden by Friem Family Brewers. The night’s highlight is the Cherry Drop—a 7-foot, lighted Bing cherry lowered at 9 p.m. to mark East Coast midnight. Held at the Milwaukie Farmers Market site, the event is ongoing and open to all ages.

New Year’s Eve Skate Party at Oaks Park, featuring a live DJ, party favors, prizes, and an extended skate session from 7 p.m. to 1 a.m. Guests can fuel up at Rick’s Roller Rink Café with burgers, nachos, and more, plus beer, wine, and cider. Tickets range from $25 for skating to $30 with a champagne toast, while spectator options start at $9. Admission includes skate rental; parking is free.

New Year’s Eve Concert with the Oregon Symphony at The Schnitz featuring Portland's own Pink Martini.

Crawl ‘Til The Ball Falls: Portland NYE Bar Crawl 2026. Grab a wristband for drink specials and no cover charges at participating bars and clubs.

Native American New Year’s Eve Sobriety Powwow returns for its 38th year, bringing one of the nation’s largest alcohol‑free celebrations back to the Oregon Convention Center. Families and community members will welcome 2026 with drums, songs, dancing and a full lineup of activities — from youth events in the afternoon to a dance exhibition, the Evening Grand Entry at 6, and a special sobriety countdown before midnight.