Together, Portland Mall Management, Inc. and Pioneer Courthouse Square are hosting the 2nd Annual Great Figgy Pudding Caroling Competition that was originally held throughout Downtown in the early 90s. Figgy Pudding is a fun and festive event that will bring caroling groups of all ages to the heart of downtown.

This FREE caroling competition will be held on Friday, December 11, rain or shine, from 5:30pm – 7:30pm and will be judged by The Dickens Carolers. Participating groups will sing their choice of holiday songs at various locations along the downtown transit mall from 6pm-7pm. At 7pm, The Dickens Carolers will announce the top three groups, who will perform one last song on stage at Pioneer Courthouse Square. The group with the most audience applause will be selected the first place winner and will leave with a $1,000 grand prize! Prizes for second, third, and the coveted People's Choice will also be awarded.

The Fireside Carolers will walk along SW 5th and SW 6th Avenues caroling from 1pm-2pm on Sunday December 13th. The Fireside Carolers are a group of professional musicians who sing holiday songs with a jazz twist, all in eight-part harmony. Look out for them on the mall! 

On December 17th at 5pm, local contemporary acapella group Without Apology will perform a set of holiday songs at SW 5th and SW Morrison. Without Apology is an all-male chorus that was formed in 2011. 

Join The Original Photo Booth on Friday December 18th to capture special photos of you and yours this holiday season in downtown Portland!  This classic photo booth experience provides vintage photos with modern day technology.  Participants receive two sets of four portraits, one for yourself, and one to share!  It’s the perfect way to share holiday moments in time.  The booth will be set up at SW5th and SW Morrison Streets from 5pm – 6pm.

The Dickens Carolers will stroll along SW Morrison and SW Yamhill performing holiday songs on Saturday December 19th from 12pm-1pm and Sunday December 20th from 12:15pm-1:15pm. The Dickens Carolers are a group of four carolers that dress in Old English costumes that date back to the 1840s. They have been performing in and around Portland since 1985 and are crowd favorites!

The Sugarplum Elves will perform at SW 6th and SW Morrison on December 20th from 11am-12pm. This variety act is comprised of performers dressed in festive elf costumes who sing, dance, and spread holiday cheer. The elves encourage singalongs and audience participation and offer charming and upbeat entertainment that is kid-friendly and fun for adults!

Want a sweet treat on us? PMMI will be providing free afternoon pick-me-ups during three days in December!

Hot Chocolate Giveaway - Thursday December 17
Enjoy free hot chocolate from Caffe Viale at Congress Center on SW 5th and SW Salmon at noon while supplies last!

Cinnamon Almonds Giveaway - Friday December 18
Get yourself a bag of Moondrops roasted cinnamon almonds! While supplies last, PMMI will be walking along SW 5th and SW 6th Avenues handing out these locally roasted nuts. 

The 25th Annual Tuba Christmas Presented by SmartPark will take place on Saturday, December 12th from 1:30pm-3:00pm at Pioneer Courthouse Square. Downtown will pulse with the melodic sounds of big brass as over 275 tubas play in unison. This annual seasonal performance is FREE for the public to enjoy and is conducted and curated by retired Oregon Music Educator Chuck Bolton. For more information or to register, click here.

Throughout the month of December, Pioneer Courthouse Square will host fun and festive performances by local school groups, choirs, dance troupes, and more! All performances are free to attend. Click here for a full list of events.

Downtown Portland is dressed up for the holidays —are you?  Come do your holiday shopping downtown and enjoy some monumental attire around Pioneer Courthouse. Our statue mascots have some festive surprises in store for you.

Beginning Tuesday, November 10, some of downtown’s most iconic sculptures will don their holiday finery for the season. In the Pioneer District on Southwest Yamhill and Morrison streets (between Fifth and Sixth avenues), you’ll see Animals in Pools, Allow Me (aka “Umbrella Man”) and Kvinneakt dressed up in festive ugly sweaters.

A team of local fiber artists will descend upon downtown and make these so-ugly-they’re-cute wardrobe changes on Thursdays through Christmas. You can join in on the fun: Wear your ugly sweaters downtown and take selfies with these yarn-bombed statues. Be sure to tag pictures with #uglysweaterpdx.

With your help, it won’t just be the statues staying warm this holiday season. The Transition Projects warm clothing drive welcomes donations of new or gently used warm winter clothing. You can drop off donations at the following locations from Tuesday, November 10 through Thursday, December 24:

•          Boys Fort- 902 SW Morrison
•          Nordstrom- 701 SW Broadway
•          Pioneer Place- customer Service Kiosk, lower level near the Gap
•          PDX Pop Up Shops- 438 NW Broadway and 341 NW 5th Avenue
•          Travel Portland Visitor Information Center at Pioneer Courthouse Square

For more information on downtown events and happenings this season, please visit www.downtownportland.org.