Tonight, December 9th, Portland Mall Management, Inc. and Pioneer Courthouse Square are hosting the 3rd Annual Great Figgy Pudding Caroling Competition that was originally held throughout Downtown in the early 90s. The Great Figgy Pudding Caroling Competition is a fun and festive event that will bring caroling groups of all ages to the heart of downtown. These groups will be positioned at locations along SW Yamhill and SW Morrison Streets from SW 3rd to SW Park Avenues and will carol from 6:00pm-7:00pm. The competition will be judged by Portland's own The Dickens Carolers. Groups will receive points for caroling, costumes, and originality. At 7:00pm, the top three groups will have a carol-off on stage at the Square! The grand prize winner will receive $1,000! Prizes will also be awarded for second, third, and the coveted People's Choice Award.

The Fireside Carolers will sing a set of traditional and contemporary holiday songs Sunday, December 11th. The Fireside Carolers will stroll along SW Yamhill and SW Morrison Streets from 12:00pm-1:00pm caroling and spreading holiday cheer!

On Thursday, December 15th and Friday, December 16th, get a bag of cinnamon sugar roasted almonds from local roaster NW Nut! These delicious, handmade sweet treats will be available starting at 12:00pm along SW 5th and SW 6th Avenues while supplies last! NW Nut is also selling fresh made roasted nuts at the Square December 9th-11th and 17th-23rd from 9:00am-9:00pm!

Take a fun and festive photo with The Original Photo Booth! On Thursday, December 15th, the booth will be set up at SW 5th Avenue and SW Morrison Street from 5:00pm-6:00pm outside of Pioneer Place. Take a break from shopping and get your photo taken! 

Returning favorite The Dickens Carolers will sing seasonal music and stroll along SW Yamhill and SW Morrison! The Dickens Carolers wear Old English costumes, perform traditional songs in a four-part harmony, and have been in Portland since 1985. The Dickens Carolers will perform on Saturday, December 17th, and Sunday, December 18th, from 12:00pm-1:00pm both days, strolling along SW Yamhill and SW Morrison Streets for all to enjoy!

Upbeat acapella group The Portland Timbre will perform on Thursday, December 22nd! Join them at SW 5th Avenue and SW Morrison Street from 12:00pm-1:00pm for a set of fun, mashup-style songs from Portland's "Treble Makers"! 

The holidays are not available online! Head downtown for the best holiday gifts for the loved ones on your list, and maybe you’ll find some treats for yourself while you’re at it. Visit longtime favorites Nordstrom, Macy’s, Powell’s Bookstore and Pioneer Place and new businesses including Well Made Goods featuring cool clothes for rad ladies; Kiriko Made, local producer of modern clothes made from vintage fabrics from Japan; and Hello from Portland, filled with incredible gifts produced by local artists. If all that shopping makes you hangry, you can stop at Pine Street Market or experience tea service at the new Headwaters at the Heathman Hotel to refuel.

PDX Pop-Up Shops have popped up again this year, turning Portland’s vacant retail space into temporary stores where local designers and artists can “set up shop” for the holiday season. The program showcases local design talent, encouraging downtown shoppers to seek out unique gift offerings this holiday season. The shops are located at 606 SW 9th Avenue. This year’s local talent includes:

Faith Hats
Via Raiz
Blanchet House of Hospitality
Micro Enterprise Services of Oregon (MESO)

PDX Pop-Up Shops are open through Saturday, December 24. Hours are Tuesday through Saturday 11 a.m. to 7 p.m., Sunday noon to 5 p.m., and closed Mondays.

Be sure to stop by former pop up shop now permanent store Boys Fort as they support other local entrepreneurs by hosting their own Pop-Up Shops this season: Beyond the Fort features local brands Adelina, Amara, Menagerie, and Frock.

On three Sundays in December, parking at SmartPark is the best deal you can find — it’s free! On Dec. 4, 11 and 18, customers who park at a SmartPark garage can visit the customer service kiosk at Pioneer Place (lower level near the Gap) or Director Park (SW Park and Yamhill) any time between noon and 5 p.m. to show their eligible SmartPark ticket for the day and receive one $5 parking voucher to cover parking for the day.

For more than 20 years, over 750 trees are lit up to add to the holiday festivities downtown. On Yamhill and Morrison streets between 5th and 6th Avenue, look for a special installation of snowflakes lighting up the night skies; this year it will be snowing all season long around Pioneer Courthouse.

For more information on downtown events and happenings this season, please visit www.downtownportland.org, Facebook: Downtown Portland, Twitter: InDowntownPDX; and Instagram: DowntownPDX.