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40+ Holiday Events in the Portland Area 2019

  |  Neighborhood Insight, Portland

‘Tis the season! The Portland area is teeming with activity this time of year — from tree lightings to Santa visits and festive musicals to holiday markets. Maximize the season by adding one (or several!) of these local events to your calendar this year.

These holiday events in the Portland area might just make the happiest time of the year even happier for you and your family. Happy Holidays!


Portland’s Singing Christmas Tree

November 22-24, 29-30, December 1

Keller Auditorium, Portland

Portland’s Singing Christmas Tree has been a holiday tradition for 57 years. This two-hour musical production showcases both contemporary and traditional holiday music performed by over 350 adult and youth choir voices, plus dance numbers from the Jefferson Dancers and special numbers by local actors and musicians. This year, Portland’s Singing Christmas Tree is taking place the weekend before Thanksgiving and the weekend right after. Get your tickets before this popular event fills up!


It Happened One Christmas

November 27 – December 22 | Varying Times

Broadway Rose New Stage Auditorium, Tigard

The Broadway Rose Theatre Company is presenting a joyful new musical from the creators of Your Holiday Hit Parade. Take a fanciful trip to “Santa’s Chalet” in the heart of the Grimble’s department store on a snowy Christmas Eve. Join Walter, the security guard, and Frances, the cleaner, as their holiday dreams spring to life while they make their evening rounds!


Portland 35th Annual Tree Lighting Ceremony

November 29 | 5:30–6:30 p.m.

Pioneer Courthouse Square, Portland

On the day after Thanksgiving, join the crowd of more than 25,000 Portlanders under the spectacular 75-foot Douglas Fir at Pioneer Courthouse Square. Enjoy a sing-along led by Thomas Lauderdale, members of Pink Martini, a variety of talented musicians and chorale singers. And of course, watch the mayor, city dignitaries and Santa Claus flip the switch to illuminate 14,000 colorful lights on the city’s tree!


Lake Oswego 55th Annual Tree Lighting Festival

November 29 | 5:30–8:30 p.m.

Millennium Plaza Park, Lake Oswego

The City of Lake Oswego and the Lake Oswego Chamber of Commerce invite you to the 55th Annual Tree Lighting, featuring two special light demonstrations and a variety of activities. First, gather at the corner of 5th Street and A Avenue in Lake Oswego to light the Bigelow Plaza Tree, then parade to Millennium Plaza Park to watch the Millennium Tree come to life! This event features performances from Lakeridge and Lake Oswego High School choirs and the Millennium Concert Band. Plus, enjoy sweet treats and the fire department’s delivery of a special guest straight from the North Pole!


The Christmas Bazaar

November 29–December 8 | 10 a.m.–6 p.m. (Fridays + Saturdays), 10 a.m.–5 p.m. (Sunday)

Portland Expo Center, Portland

Christmas Bazaar Portland, OR

Photo Courtesy of The Christmas Bazaar

Get your shopping done at the largest Christmas bazaar in America this year. Taking place at the Portland Expo Center, The Christmas Bazaar will feature 400 booths of juried handcrafted items plus 500 booths of commercial holiday products. The Christmas Bazaar is open on Fridays, Saturdays and Sundays and admission is $8 for adults, $3 for children ages 12–17, and free for kids under 12.


The Holiday Express Train

November 29–December 15 | Varying Times

The Oaks Station, Portland

Ride in vintage rail cars behind Portland’s historic steam locomotives and get the opportunity to visit with Santa Claus on board the Holiday Express Train. This festive train ride is one of the city’s most beloved traditions. Proceeds benefit the Oregon Heritage Foundation whose mission is to provide for the preservation, operation and public enjoyment of Portland’s historic locomotives, railroad equipment, artifacts and to educate the public about Oregon’s rich and diverse railroad history. Take a look at the train’s availability and book your tickets to embark on this magical journey!


Gloria With PCO and Big Horn Brass

November 30 | 2 p.m. + 5 p.m.

Newmark Theatre, Portland

Featuring 13 brass and two percussion instruments, Big Horn Brass is a talented team of musicians based in Marylhurst, Oregon. They are putting on three special holiday concerts this year, including Gloria with the Portland Choir & Orchestra. Choose from two performances of the show, at 2 p.m. or 5 p.m.


Miss Bennet: Christmas at Pemberley

November 30–December 29 | Varying Times

Portland Center Stage at The Armory, Portland

Miss Bennet: Christmas at Pemberley

L-R: Treasure Lunan, Cindy Im, Lauren Modica, and Kailey Rhodes as the Bennet sisters in “Miss Bennet: Christmas at Pemberley.” Photo by Kate Szrom.

A sequel to Jane Austen’s Pride and Prejudice, the charming and clever story of Miss Bennett: Christmas at Pemberley tells the story of middle sister Mary, who has grown tired of her role as the dutiful daughter. When the family gathers for the holidays, Mary encounters an unexpected guest. This romantic comedy blends modern wit with period style, enchanting both Austen fans and newcomers alike. You have several opportunities to see the show, including both matinee and evening performances, all throughout the holiday season!


A Christmas Carol With Portland Playhouse

November 30–December 29 | Varying Times

Portland Playhouse, Portland

Enjoy a special performance of “A Christmas Carol” at the Portland Playhouse throughout the month of December, as talented actors, musicians and directors come together for an evening celebrating Charles Dickens’ classic Christmas tale. This particular production has won three awards, including Best Play, Best Ensemble and Best Director. Tickets start at just $19 (for the preview performances).


It’s a Tony Starlight Christmas

December 3–30 | Varying Times

Tony Starlight Showroom, Portland + Revolution Hall, Portland (Final Evening)

Reminiscent of the classic holiday TV shows of years past featuring entertainers like Bing Crosby or Dean Martin, “It’s a Tony Starlight Christmas!” is sure to spread holiday cheer and make you laugh. Tony has joined forces with Bo Ayars for a Vegas-style Christmas program like nothing you’ve ever seen. The show is both silly and sweet, and appears well-rehearsed yet still spontaneous. Get your tickets to this memorable show for any of the several performances throughout the month of December!


Holiday Ale Festival

December 4–8 | 11 a.m.–9 p.m. (Wed.–Sat.) + 11 a.m.–5 p.m. (Sun.)

Pioneer Courthouse Square, Portland

Each year, the Holiday Ale Festival unites beer lovers with dozens of winter warmers for a joyous five-day celebration in the heart of the city. This quintessential Portland event has earned a reputation as the premier winter beer tasting venue on the West Coast. Stay warm and dry under a large clear-top tent covering Pioneer Square with gas heaters all around. More than 50 winter ales and ciders are featured at this year’s event, all of which were created specifically for the holiday season. From Belgians to barleywines, and stouts to sours, these beers are rich, robust and full of complexity. Purchase $40 general admission advance tickets, which includes a festival glass, 12 beer tickets and expedited entry all five days — or take it to the next level with the GA GiftPass Tickets ($80) or the Enthusiast VIP Tickets ($100).


12th Annual White Album Xmas

December 4–14 | 8 p.m.

Alberta Rose Theatre, Portland

This annual tradition is both a holiday circus spectacular and tribute to The Beatles. The NowHere Band, a 15-piece orchestra, will perform the Fab Four’s entire classic “White Album” while the Rose City Circus performs amazing, high-flying feats. Purchase your tickets for $37.50 in advance, $47.50 at the door, or $57.50 for premium seating, before this popular show sells out!


Ainsworth Holiday Home Tour

December 5 | 9:30 a.m.–1 p.m. + 5:30–8:30 p.m.

Ainsworth Elementary School, Portland

As a real estate company, this event is one we are especially excited about! The Ainsworth Holiday Home Tour offers an exclusive look inside a handful of decorate homes in the Southwest Hills area. Now in its 33rd year, the tour is the largest fundraiser for Ainsworth Elementary School. Funds raised directly benefit the students by providing computers, enhanced art programs, field trips, classroom supplies, and other support to teachers and staff.


A Christmas Carol the Musical

December 5–22 | Varying Times

Winningstad Theatre, Portland

Broadway stars Alan Menken and Lynn Ahrens breathe new life into a classic tale with “Christmas Carol the Musical” at Winningstad Theatre. Take a journey through the past, present and future with grumpy Ebenezer Scrooge, as he recognizes his faults and eventually shares the holiday with those who mean the most to him. Enjoy this spectacular performance each Thursday–Saturday at 7:30 p.m. and Saturdays and Sundays at 2 p.m. through December 22. Tickets range from $28 to $48 with discounts for students, seniors and groups of eight or more.


Duniway Home Tour

December 6 | 10 a.m.

Duniway Park, Portland

Ring in the season with this cherished Eastmoreland tradition that supports Duniway Elementary School. Take a peek inside six beautiful homes in the neighborhood decked out for the holidays, enjoy trolley rides and live music, and visit the Holiday Boutique, which will feature wares from local artists and merchants. Get your tickets for $30 in advance or $35 the day of the event.


Beaverton Tree Lighting

December 6 | 5–8 p.m.

City Park, Beaverton

Gather at Beaverton City Park for an evening of holiday magic, featuring the city’s annual tree lighting, visits with Santa Claus, a photo booth with Disney characters, s’mores and hot cocoa, library book giveaways, and sing-along songs with a holiday choir. This event is completely free to attend!


Starry Nights and Holiday Lights

December 6 | 5–8:30 p.m.

Lake of the Commons, Tualatin

The city of Tualatin comes together at the quaint lake at the Tualatin Commons for a special tree lighting ceremony. Enjoy carolers, refreshments, activities for kids, Santa visits and lots of holiday cheer. Plus, a number of choirs and ensembles will take the stage all evening long. This event is completely free!


Downtown Tigard Tree Lighting

December 6 | 7 p.m.–12 a.m.

Liberty Park, Tigard

Get in the holiday spirit at the annual downtown Tigard tree lighting, featuring an appearance from Santa and Mrs. Claus, who will arrive by fire truck and will be available for visits and hugs after the ceremony. Plus, enjoy musical performances, cocoa and cookies, and more. The festivities begin at 7 p.m. at Liberty Park!


Safeway Providence Festival of Trees

December 6–7 | 10:30 a.m.–8 p.m. (Friday) + 9 a.m.–5 p.m. (Saturday)

Oregon Convention Center, Portland

Join a crowd of 20,000 people at the 37th Annual Safeway Providence Festival of Trees, filled with fun for the whole family at the Oregon Convention Center. This year’s festival will feature more than 100 exquisitely decorated trees, mini trees and holiday displays, designed by local businesses, designers, florists and talented volunteers. Proceeds from the entire event, including the Gala Dinner and Auction on December 5 and Elf Academy happening throughout the festival, will benefit Providence Children’s Health and help them provide services and research that would not exist without philanthropy.


Hillsboro Holly Days

December 7 | 3–7 p.m.

Tom Hughes Civic Center Plaza, Hillsboro

Hillsboro Holly Days

Photo Courtesy of the Hillsboro Tuesday Night Market

The community of Hillsboro kicks off the holiday season each year with their Holly Days and Market event. Festivities begin at 3 p.m. with a special winter marketplace featuring local artists, crafts, food and drinks, fresh winter produce, and live entertainment. Head to the Tom Hughes Civic Center Plaza for an afternoon filled with holiday cheer and excitement, complete with a spectacular tree lighting ceremony at 5:30 p.m.


Milwaukie Umbrella Parade & Tree Lighting

December 7 | 3:45–6:30 p.m.

City Hall, Milwaukie

The city of Milwaukie comes together for this annual tradition each holiday season. Decorate an umbrella and parade through downtown, ending with the lighting of the tree! Parade participants are asked to convene at 3:45 and the parade steps off at 4:15. Everyone is welcome to decorate an umbrella and participate in the parade; no pre-registration is required. And don’t miss the tree lighting at 5 p.m., complete with delicious cookies, hot chocolate and apple cider, grilled cheese bites, Santa Claus visits and more!


George Balanchine’s The Nutcracker®

December 7–26 | Varying Times

Keller Auditorium, Portland

Embark on a journey to a familiar place filled with warmth, tradition, and new memories waiting to be made. Oregon Ballet Theatre’s annual performance of George Balanchine’s “The Nutcracker” has been a holiday staple for more than 15 years. Become immersed in this classic story with magnificent scenery and elaborate costumes. The OBT Orchestra will perform live at 12 of the 18 performances throughout the month of December. Get your tickets for this magical performance at the Keller Auditorium!


A Christmas Festival With Big Horn Brass

December 8 | 6:30 p.m.

St. Matthew Lutheran Church, Beaverton

Featuring 13 brass and two percussion instruments, Big Horn Brass is a talented team of musicians based in Marylhurst, Oregon. They are putting on three special holiday concerts this year, including A Christmas Festival, featuring the music of Stan Kenton and Northwest composer Anthony DiLorenzo, alongside festive favorites. The St. Matthew Exaltation Handbells will provide a pre-concert show at 6:10, and the concert begins with a candle lighting service accompanied by the Big Horn Brass.


Gospel Christmas

December 13–15 | 7:30 p.m. (Friday + Saturday), 4 p.m. (Sunday)

Arlene Schnitzer Concert Hall, Portland

Gospel Christmas has been a community tradition for more than 20 years. Each year, the region’s premier gospel singers and the Oregon Symphony join together for an exhilarating and uplifting concert experience embodying the true spirit of the season. Purchase tickets starting at $35 for the performance on Friday, Saturday or Sunday!


Handel’s Messiah With the Portland Baroque Orchestra

December 13–16 | 7:30 p.m. (Friday, Saturday + Monday), 3 p.m. (Sunday)

First Baptist Church, Portland

Handel’s Messiah With the Portland Baroque Orchestra

Photo Courtesy of Jonathan Ley via the Portland Baroque Orchestra

Experience an awe-inspiring performance from the Portland Baroque Orchestra as they play one of the most-performed and well-regarded works in all of musical history. Monica Huggett leads the orchestra in Portland’s only annual production of this holiday tradition on period instruments. Enjoy a Complete Oratorio, lasting about three hours, on Friday, Saturday or Sunday, or the Messiah Highlights at the Monday performance. Tickets for the concert start at $34.


29th Annual Tuba Christmas Concert

December 14 | 1:30–3 p.m.

Pioneer Courthouse Square, Portland

Downtown comes to life with this exciting annual tradition, featuring nearly 300 tubas playing in unison in Pioneer Square. The 29th Annual Tuba Christmas Concert will play from 1:30–3 p.m. and is free and open to the public. Interested in playing? Register here to play in the concert!


A Christmas Festival With Big Horn Brass

December 14 | 7:30 p.m.

Milwaukie High School Auditorium, Milwaukie

Featuring 13 brass and two percussion instruments, Big Horn Brass is a talented team of musicians based in Marylhurst, Oregon. They are putting on three special holiday concerts this year, including A Christmas Festival, featuring the music of Stan Kenton and Northwest composer Anthony DiLorenzo, alongside festive favorites, at the Milwaukie High School Auditorium.


Portland Bazaar

December 14–15 | 11 a.m.–4 p.m.

Yale Union, Portland

The Portland Bazaar is the city’s finest holiday gift showcase and sale. For the ninth year, the Portland Bazaar is putting on a party with lots of food, wintery cocktails and holiday shopping from over 70 Portland makers, artists and small businesses. The bazaar is free to attend and open to all!


Crafty Wonderland Holiday Art + Craft Market

December 14–15 | 11 a.m.–6 p.m.

Oregon Convention Center Hall D, Portland

Don’t miss the Crafty Wonderland Holiday Art + Craft Market, where you can shop from 250+ artists and crafters selling amazing handmade goods at the expansive Oregon Convention Center. Get tickets for the exclusive pre-show ticketed shopping event on Friday evening (5–9 p.m.) or enjoy free admission on Saturday and Sunday from 11 a.m. to 6 p.m. You’ll want to arrive early, as the first 150 people through the doors each day will receive a special goodie bag!


A Nutcracker Tea

December 14–22 | Varying Times

PCC Sylvania’s Performing Arts Center, Portland

A Nutcracker Tea Portland, OR

Photo Courtesy of Lindsay Hile Photography via the Northwest Dance Theatre

Enjoy a family-friendly abridged version of Marius Petipa’s Nutcracker Ballet, featuring music by Pyotr Ilyich Tchaikovsky. This classic story is presented by Northwest Dance Theatre with elaborate sets, stunning costumes, and sparkling choreography. Even if you’ve seen this performance in years past, Northwest Dance Theatre never fails to incorporate exciting new twists and turns to enhance each season’s performance. Complimentary tea will be served to complete the experience! Tickets range from $19–35.


CELEBRATE Chanukah! A Family Festival

December 15 | 9 a.m.–12 p.m.

Neveh Shalom, Portland

Congregation Neveh Shalom is hosting a family festival for CNS, Foundation School and Shoreshim families. The event will feature Chanukah-themed art projects, music and stories, dreidel-playing, and Chanukah treats.


Comfort & Joy: A Classical Christmas

December 18 | 7:30 p.m.

Arlene Schnitzer Concert Hall, Portland

Enjoy light holiday classics, seasonal favorites and a very merry sing-along at this jubilant evening at the Arlene Schnitzer Concert Hall. Led by Conductor Norman Huynh, The Oregon Chorale will enchant the audience with classical holiday music. Tickets for “Comfort and Joy: A Classical Christmas” start at $25.



Lighting of Maddax Woods

November 16–December 31

Maddax Woods, West Linn

Head to West Linn for a magical walk down a lighted, accessible path winding through Maddax Woods, leading to a viewing platform along the Willamette River. Along the way, search for creatures, view new Maddax’s boat history and see Dorothy Maddax’s garden! The lights will be turned on November 16 and the woods are open for exploration each evening through December 31.


Gingerbread Adventures at OMSI

November 16–January 2

Oregon Museum of Science and Industry, Portland

Put a holiday spin on your visit to the Oregon Museum of Science and Industry (OMSI) with their special “Gingerbread Adventures” exhibit. Take a sweet (and smart!) look at the science behind a favorite holiday pastime — making gingerbread houses. See the brilliant masterpieces from expert bakers and architects, who worked together to build towering gingerbread sculptures. The exhibit is included with general admission to the museum.


A Pittock Mansion Christmas: Wonderful World of Books

November 25–January 5

Pittock Mansion, Portland

A Pittock Mansion Christmas

Photo Courtesy of Pittock Mansion Society

Explore the breathtaking holiday decor at the historic Pittock Mansion, a local tradition for over 50 years. This year, explore the wonderful world of books, from children’s classics to modern-day mysteries, as local decorators transform the mansion’s rooms into magical storybook settings. The festivities extend through January 5, but Pittock Mansion will be closed on Thanksgiving and Christmas Day. This annual tradition should not be missed! Admission is free for members, $13 for adults, $11 for seniors, $9 for ages 6–18, and free for children under 6.



November 29–January 5

Oregon Zoo, Portland

An annual tradition for many in Portland, the Oregon Zoo’s annual ZooLights is an enchanting event featuring more than 1.5 million dazzling lights. You will see the zoo in a whole new light, as you visit with animals, ride the popular lighted train, hear live music, sip on warm drinks, and enjoy dinner from a number of food trucks. Plus, Santa will be on site for photos through December 24! Take a look at the calendar to see pricing for ZooLights (keeping an eye on the special Value Nights).


Winter Wonderland

November 29–January 4

Portland International Raceway, Portland

Considered the largest drive-through holiday light show west of the Mississippi, the 27th annual Safeway Winter Wonderland, powered by Advantis Credit Union, will grab your attention with glimmers and glows around every corner. Spectators enjoy a spectacular drive-through light show with over 250 colorful light set pieces and fully animated scenes. Admission costs $22 per car from November 30–December 12, or $24 per car from December 13–January 4. All proceeds from the event benefit Sunshine Division, a nonprofit providing food and clothing relief to local families since 1923. Take a look at the event website for additional pricing details and the various special events happening at Winter Wonderland throughout the season.


The Grotto’s Christmas Festival of Lights

November 29–December 30

The Grotto, Portland

Considered the largest Christmas choral festival in the world, the Grotto’s Christmas Festival of Lights features more than 160 indoor holiday concerts performed by many of the region’s finest school, church and civic choirs. There are five indoor concerts scheduled each evening in The Grotto’s 500-seat chapel known for its cathedral-quality acoustics. Enjoy family entertainment in the plaza area, including caroling, puppet shows, a live petting zoo, holiday food and beverages, and seasonal shopping in the gift shop. Tickets may be purchased at the gate from 5–9:30 p.m.; admission is $12.50 for adults, $11.50 for seniors/military, $6.50 for children, and free for children 2 and under.


Christmas Ship Parade

December 5–22

Various Locations

For 15 nights in December, take in the wonder of the Christmas Ship Parade along the Columbia and Willamette Rivers. Take a look at the Columbia River Schedule and the Willamette River Schedule for the dates and times of parades as well as the best viewing locations — from shoreline parks to cozy riverfront restaurants. Watch decorated boats pass by with vibrant colors reflecting off the water’s surface and experience the joys of this annual Portland tradition!


Meier & Frank SantaLand at the Oregon Historical Society

December 6–January 3

Oregon Historical Society, Portland

Meier & Frank SantaLand at the Oregon Historical Society

Photo Courtesy of the Oregon Historical Society

If you’ve lived in the city for a while, you may remember Santaland at the Meier & Frank department store in downtown Portland with its iconic monorail and a chance to sit on Santa’s lap. Following the closure of Macy’s downtown store, which purchased Meier & Frank in 2005, items from Santaland were donated to the Oregon Historical Society and the Portland Business Alliance. See these nostalgic pieces on display at the OHS — including Santa’s chair, Rudolph, animatronic elves and a decorated Christmas tree! And new last year, you can even see a model of the famous monorail on display. Plus, visit with Santa on December 8, 14 and 21!


The Miracle of a Million Lights

December 8–28

Victorian Belle, Portland

During the month of December, Victorian Belle transforms into a Christmas wonderland for “The Miracle of a Million Lights.” Explore this historic landmark with over a million twinkling lights, 20+ uniquely decorated Christmas trees, and elaborate decor all around. View rooms filled with period antiques and vintage heirlooms displaying majestic themes. In addition to the tour, enjoy homemade apple cider and holiday cookies, while you listen to live musical performances. Roast marshmallows for s’mores by the fire with Rudolph, make a craft with Mrs. Claus, and admire the impressive model railroads.


Peacock Lane Christmas Lights

December 15–31

Peacock Lane, Portland

Nicknamed “Portland’s Christmas Street,” Peacock Lane is considered one of the city’s most popular destinations and traditions during the holiday season. Each home in this quaint southeast neighborhood has been decorating for Christmas for decades. Mostly comprised of Tudors, this historic neighborhood features beautiful sparkling lights, nativity scenes, rotating Christmas trees and life-like replicas of your favorite holiday characters. Because the streets can become crowded, it is wise to park several blocks away and walk to the street. Peacock Lane will be decorated and ready for visitors from 6–11 p.m. December 15–31. The street will be pedestrian-only and closed to cars on December 15, 16 and 17. This event is the Peacock Lane homeowners’ gift to Portland so there is no charge to view the lights!


Happy Holidays!

What Portland area holiday events do you look forward to each year? Let us know in the comments below!

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About the Author

Melissa Peterson, Director of Agent Services and Technology

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