Santa, singing trees and plays—oh my! The season of cheer is gearing up in Portland, and our fair city has a whole lot of fun in store for families. Whether you are in the mood to do some shopping, take in live theater or hang out with real life reindeer, there’s something magical lined up for you this weekend. Read on to find our top picks for things for families to do.

photo: via unsplashed

SW Portland

Check Out Portland Singing Christmas Tree
For over 50 years, Portland’s Singing Christmas Tree has been a holiday tradition at the Keller Theater, with a wide range of Christmas music performed by over 350 choir members of all ages. The Jefferson Dancers, performances by actors and musicians, and a cinematic Nativity combine to create a multi-dimensional show. This year features new music and a new story.  Recommended for ages six and up due to the long running time . All kids over the age of one require a ticket. Fri. Event Details.

Visit Santa at Pioneer Place Mall
There’s no place quite as Portlandy as Pioneer place! Looking for that traditional pic with Santa? Have a furry family member who wants to ask the jolly guy for a new chew toy? How does being as unique as Portland with a visit Hipster Santa sound? Pioneer Place Mall offers all these awesome opportunities. Head online to reserve your spot, choose packages, and look at photos.  Get a jump on to get photos early. Fri., Sat. & Sun. Event Details.

NE Portland

Stroll Through the Olio Nuovo Festival
Oregon’s annual olive oil celebration is back for its tenth year! Olio Nuovo (‘new oil’) is Durant Olive Mill’s complimentary festival honoring the completion of this season’s olive harvest and the milling of extra virgin olive oil. Enjoy complimentary appetizers including traditional Italian bruschetta, freshly baked baguette, and classic mozzarella all served with olio nuovo. Have a taste of Durant Vineyards estate wine while taking in the epic Willamette Valley views. Join our Olive Miller’s for a tour of Oregon’s only commercial olive mill, offered every 30 minutes. Live music, cooking demos, and discover some of Oregon’s top food producers in the Local Marketplace Tent at Durant Vineyards Wine Tasting Room. Meander through Red Ridge Farms Nursery & Gift Shop where you’ll find everything you need to build a holiday centerpiece or tablescape. Shop locally crafted wreaths, holiday decor, houseplants, olive oil body care, local cookbooks, and more! Fri. & Sat. Event Details.

SE Portland

Check Out The Music Man
Funny, romantic, charming, and terribly clever, The Music Man is family entertainment at its best. Meredith Willson’s six-time, Tony Award-winning musical comedy has been entertaining audiences since 1957 and is a family-friendly story to be shared with every generation. Fri., Sat. & Sun. Event Details.

Attend Lloyd Center Tree Lighting
Bring a little light and magic to the long dark days of winter at Lloyd Center’s official tree lighting with Mr. and Mrs. Claus. Be mesmerized as snow falls over the ice while you enjoy a short skating performance and music at the Lloyd Center Ice Rink. Sat. Event Details. 

Don’t Miss the All American Magic & Ventriloquist Show
Get ready for two hours filled with head-scratching illusions, music and the hilarious comedy magic of Mark Benthimer and ventriloquist, Scott Davis. The theater also has a snack bar with cotton candy and popcorn for a buck, Nachos and Pretzels, plenty of free parking and an onsite Magic Shop. Buy your tickets in advance online because the show sells out every time! Sat. Event Details.

Head to the Specials Thanksgiving Farmers Market
This Special Thanksgiving Market will be held the Sunday before Thanksgiving on November 24th. Pick up all your fixings for your Thanksgiving meal or start to check off your gift list for those hard to shop for loved ones! There will be have a nice selection of your favorite vendors along with some new, seasonal vendors as well.Sun. Event Details.

Mt. Hood

Experience Mt. Hood Railroad Train to Christmas Town
While Mt. Hood Railroad offers year-round rides, it’s holiday excursion, The Train to Christmas Town, is exceptional. The magic begins the minute you board with music and singing. You’ll meet book characters like Bumblebee the cuddly polar bear and the postman delivering letters to Santa. As if that wasn’t enough,elves dance in the aisles leading sing-alongs to Christmas songs. And wheyou hear the “Chocolate Christmas” song begin to play it’s time for cookies and hot chocolate to be served!

When you finally arrive at Christmas Town you get to wave to Santa and his elves before they climb aboard to walk through the rail cars to greet each boy and girl and present them with a special gift. Make sure to buy your tickets early for this seasonal experience. Fri. & Sat. Event Details.


Visit Santa’s Reindeer at Your Cornelius
Experience a little Christmas magic at your local Coastal brought to you by our friends at Wrangler & Justin! Visit live reindeer at your Cornelius Coastal to celebrate the Holiday Season! While you’re with us pick up some magic reindeer snacks to enjoy with hot cocoa! Make sure to write a letter to Santa, too!  Sun. Event Details.

—Annette Benedetti