Fun Winter Events in the Portland Area

Portland's Pioneer Square

Pioneer Square lit up for the winter holidays.

Winter Events around Portland

The Bridgetown team is here to take the stress out of moving and make your life easier. When we are not helping the city of Portland move, we love joining in and being a part of our community, especially during the holidays. Take advantage of the time you saved when you hired our team of experts to pack, lift, and transport your bulkiest furniture items by getting out and enjoying this season’s festivities with your family and friends. However, there’s so much to do in Portland and the surrounding area during the holidays that it can be difficult to keep track of it all. That’s why we rounded up some of the best local events for you. Take a look and see if anything catches your eye; we will see you there!

Forest Grove

The Best Christmas Pageant ever

When: Friday December 18th 7:30pm

Where: Theatre in the Grove in Forest Grove, OR

What happens when you try to run a Christmas pageant starring the worst awful kids of all time? It’s a answer you don’t want to miss from this comedy adapted from the best-selling Young Adult book. The Theatre in the Grove will be open on December 18th at 7:30pm presenting the show “The Best Christmas Pageant Ever”. Stop by the site to get ticket details.


Christmas at the Museum & Photos with Santa

When: Saturday December 19th from 10-2pm

Where: Gresham Historical Museum in Gresham, OR

Did you know that Santa likes the Museum? There will be a rare sighting of him from 10-2pm on December 19th at the Gresham Historical Museum. There will be plenty of cookies and Cider so he will definitely be sticking around! See site for more details.


Winter Village at Orenco Station ( w/ Outdoor Ice Skating!)   

When: Dec. 18 2015 – Jan. 3 2016 (closed Christmas)

Where: 943 NE Orenco Station Loop in Hillsboro, OR

For a limited time, Hillsboro will be featuring the only open-air ice-skating experience in the Portland Metro Area with Winter Village at Orenco Station! Bring friends and family to enjoy a unique winter-y fun time on the ice. Individual and group sessions are available to the public between December 18th to January 3rd. See the event page for admission details and rates.

Lake Oswego

Christmas Ships Parade/ Willamette Shore Trolley Special Christmas Excursions

When: December 16th 6:30pm-7:30pm

Where: 311 N State Street in Lake Oswego

Be part of a unique and beautiful evening of watching colorful Christmas ships sail on the Willamette, while you ride in the comfortable pace of a Trolley from Lake Oswego. This s a one time special event on December 16th from 6:30-7:30, and spots fill out fast! See event page for details and reserve your spot now!

Holiday Magic Breakfast Theatre

When: Select dates up till December 20th ; Show times at 9am and 11am

Where: Lakewood Center for the Arts in Lake Oswego

First premiering in Portland, the “Peppermint Bear Show : The Taming of the Shoe” has been widely produced all over the country, now becoming a popular tradition in the past 30 years. Enjoy a holiday continental breakfast before the show, then let the story unfold. See site for viewing times and admission details.


Illuminate your Holidays at Bridgeport Village  

When: Ongoing until Friday December 18th. 10am to 8pm

Where: 7455 SW Bridgeport Rd in Portland, OR

At Bridgeport Village, there will be a myriad of activities and sights to see up till December 18th. Enjoy Breakfast with Santa, or snow shows with the Candy Man, Elsa, Anna and Olaf! This is a perfect place for families to experience the holidays together. See event page for more details.

Oregon City

The Winter Farmer’s Market

When: Saturday Dec 19, 10am- 2pm

Where: 2051 Kaen Road in Oregon City, OR

Winter shouldn’t keep you away from fresh locally grown food. Stop by the only Farmer’s market open during the winter at Clackamas county in Oregon city.  For one day only on December 19th from 10-2pm, find the freshest ingredients for your delicious holiday meal. See site for details.


Peacock Lane

When: December 15th-31st 6pm-11pm Pedestrian only nights December, 18-20th

Where: between SE Stark St. and SE Belmont St. and one block east of SE 39th in Portland, OR

As a long time Portland tradition, the houses along Peacock lane will light up and dazzle once again this Christmas from December 15th till the 31st from 6pm-11pm. Tour the spectacular light shows and beautiful nativity scenes with friends and family, because it’s a one of a kind show! See site for more details.

SunShine Division Winter Wonderland

When: Ongoing until December 27th

Sunday – Thursday 5pm-9pm

Friday through Saturday 5pm-11pm

Where: Portland International Raceway in Portland, OR

Only 7 miles away from downtown portland, Safeway and Albertsons will once again be hosting their annual  drive through Winter Wonderland. Often dubbed as the “Largest Holiday Light show West of the Mississippi”, the event will be a spectacular glittering sea of 200+ light shows across the raceway. This Winter Wonderland will be open till December 27th, see site for more details and admission fees.

Portland Holiday Express

When: weekends from December 12th to December 20th

Where: Oaks Park Station in Portland, OR

Ride along on the decorated Holiday Express Train as it takes you on a joy ride steaming along the Willamette River. It’ll be a warm cozy ride with plenty of sweet treats like hot cider and yummy cookies. This grand steam train decorated in pretty lights, would make Santa excited. Ride with him on December 19th and the 20th. See site for select times and tickets.

Christmas Festival of Lights at the Grotto

When: Ongoing thru December 30th from 5pm-9:30pm. Closed Christmas Day

Where: The Grotto in Portland, OR

Witness the sights, sounds and wonderful splendor of the Christmas spirit, as the finest choir groups from the region come together to perform more than 140+ concerts inside the grand Grotto. The Festival will run through the 30th of December from 5-9:30pm, and there will also be a variety of fun family activities including petting zoos and puppet shows!  See site for details and admission fees.

Oregon Zoo Lights

When: Ongoing until January 3rd 2016 from 5-9pm

Where: Oregon Zoo in Portland, OR

Experience what it’s like to navigate through the jungle of lights and decorations at the Oregon Zoo. The annual Zoolights is known for it’s colorful displays and transforming your experience at the zoo entirely. Zoolights run until January 3rd (excluding December 24th/25th), from 5-9pm. See site for details and ticket pricings.

The Magic of Wintertime at Pittock Mansion

When: Ongoing until January 2nd, 11am to 4pm; Closed on Christmas day

Where: Pittock Mansion in Portland, OR

Witness and be part of the holiday experience as Pittock Mansion transforms into a fun Winter Wonderland, glistening with lights, decorations and cheery holiday tunes. The Pittock Mansion Wintertime magic will run until January 2nd** from 11am to 4pm. See event page for more details.

The Miracle of a Million Lights

When: Ongoing until December 23rd  from 6-10pm daily

Where: At the Victorian Belle in Portland, OR

What do 1 million + lights look like? The Miracle of a Million lights at the Victorian Belle has that answer. Explore and become transfixed at the blanket of lights covering this 2.5 acres of ground. This is a unique mix of period vintage styles and the glow of the holiday season. See site for details and directions.

Alpenrose Dairy Storybrooke Lane

When: Selected dates and times from Dec. 4th-23rd.

Where: Alpenrose Dairy in Portland, OR

Visit Storybrooke Lane and have pictures taken with Santa at this annual festival event hosted by Alpenrose Dairy! Admission is free but canned food for donations are suggested. Visit the site for more details.

Cinnamon Bear Cruise on the Portland Spirit

When: Ongoing until December 27th. 10am to noon, and 2pm-4pm.

Where: The Portland Spirit Cruise in Portland, OR

Cinnamon bear returns to the Portland spirit! Bring your family onboard and join Cinnamon Bear and his friends for a lovely two hour cruise down the river. Onboard there will be plenty to do like magic shows and music performances. The cruise will run until December 27th, see site for time and admission fees.

Festival of the Last Minute 2015

When: December 17th-24th  

Where: Portland Saturday Market

Put off shopping until now? The Festival of the Last minute gives everyone a chance to find that perfect last minute gift! In addition to the unique vendors, there are many holiday festivities for enjoyment. Grab some treats or stop by and talk to Santa during your shopping experience. See site for a detailed schedule.

Christmas Ships Parade

When: Ongoing until December 20th – Evening (various times)

Where: Portland , OR

Carrying on the tradition for 50 years, more than 60 boats will beautifully display their Christmas spirit along the Willamette and Columbia river. Check site for times and schedules, you don’t want to miss the 15 new display boats this year!


Christmas in the Village: Ugly Christmas Sweater day

When: Friday December 18th – 6pm -9 pm

Where: Latte Da Coffee House in Vancouver, OR

Have a laugh! Have a scratch! Debate who has it the worst! On December 18th pick out the most ugliest sweater you own and prance on over to Latte Da Coffee house at Uptown village from 6pm-9pm. It’ll be a fun night of caroling, eating fresh hot s’mores and seeing who truly has the ugliest sweater. Everyone wants to know, see site for details.

Carols of the Winter Night- Touch of Class Chorale

When: Dec 20th at 2pm

Where: East Woods Presbyterian Church in Vancouver, OR

On December 20th at 2pm, the East Woods Presbyterian Church will open it’s doors and let you witness the powerful voices of the 40 member Community Choir as they bring the holiday spirit with them. The Choir will perform their “Carols of the Winter Night” in only 3 concerts so you don’t want to miss this. See sites for details, and admission fees.

West Linn

Music in the Stacks Ft: Mark Hanson and Greta Pedersen

When: Wednesday, December 16th 6:30pm

Where: West Linn Public Library in West Linn, OR

On December 16th 6:30pm, the West Linn public library will be hosting a very special event. Bring friends and family to enjoy a cozy evening as Grammy award winning Guitarist, and 2009 national artist Mark Hanson and Greta Pedersen strum the evening away. Having performed around the world, this is one performance you don’t want to miss. See site details for more info.


Holiday Fun Fest at  the Community Center

When: Wednesday, December 16th

Where: Wilsonville Community Center in Wilsonville, OR
How about making your day a little bit more warmer and sweeter? The Wilsonville Community Center is hosting their annual Holiday Fun Fest at noon on December 16th. Bring your kids and enjoy a fun afternoon crafting yummy gingerbread houses and sipping hot chocolate! It’s so fun even Santa will be there! See event page for more details.