Events in Oregon’s Mt. Hood Territory offer year-round festivals and activities for the whole family in the greater Portland area. Winter’s event calendar is full of snowboarding and skiing events at Timberline Lodge & Ski Area and Mt. Hood Skibowl, plus holiday happenings at Christmas tree farms. Spring events burst upon the scene with blooming flowers and baby farm animals galore. Summertime is filled with an abundance of outdoor activities, festivals, music events, and Farmers' Markets. Celebrate the fall bounty as local communities provide family fun harvest festivals, corn mazes, pumpkin patches, and haunted trails. The Clackamas County Fairgrounds & Event Center offers a variety of events throughout the year, including the Clackamas County Fair and Rodeo. See below for upcoming events, or click the links in the text above for more information on some of our seasonal favorite activities.
Note: We strive to keep all event listings up-to-date, but please check event status with individual event hosts before planning your trip.
Time: 12 - 10pm
Address:
1109 SW 1st Ave, Canby, OR 97013
Enjoy Christmas movies and build or eat gingerbread houses! Bring your own gingerbread house and FOB Taproom will have the movies and beer! Cheers and Happy Holidays!
Visit our list of area tree farms with winter season activities for all ages. Our handy map will make it easy to find the perfect tree farm or experience near you! Area tree farms offer U-cut, pre-cut and even trees delivered right to your door! A vast varieties for activities include wreath making classes, visits with Santa, hot cocoa, holiday treats, train rides, warming stations, petting zoos, hay wagon rides and so much more! Visit the list for full details.
Time: 5 - 9pm
Address:
694 NE 4th Ave, Canby, OR 97013
Phone: 503-266-1136
Ho ho ho! Gather ’round, my merry friends, because this year’s Winter Fair is going to be more magical than ever before! To keep things exciting this years route for the twinkling lights has changed and this year you’ll now embark on a delightful journey down to the rodeo arena! Along your way, you’ll be dazzled by what's been crafted with over 200,000 shimmering lights and enchanting scenes. This half-mile walk will whisk you through tunnels of wonder, leading you straight to the arena, where a 30-minute Christmas tree show will light up the night with joy! After you’ve soaked in all those dazzling lights, head inside to warm your hands and heart with a cup of hot cocoa. And don’t forget to check out our over 30 festive vendors—perfect for finding those special gifts for family and friends!
Time: Tues-Fri, 10am–5pm, Sat 10am - 2pm
Address:
380 A Street, Lake Oswego, OR 97068
Phone: 503-272-1214
The Arts Council of Lake Oswego's annual Holiday Marketplace has begun at Artspace! The gallery is filled with unique, meticulously crafted wares by talented regional artists and artisans, inviting you to celebrate local creativity and craftsmanship. Find a truly unique gift for a loved one or yourself and support your local economy. All proceeds benefit the artists in the show and free arts programming at Artspace.
Time: 10am - 2pm
Address:
29700 SW Mountain Rd, West Linn, OR 97068
Come for pictures with Santa and his animals helpers. Stay for bounce house fun and food!
Time: 1 - 2pm
Address:
27221 S Dryland Rd, Canby, OR 97013
Visit Santa Cow! Bring your kids, your crew or just your Christmas cheer and snap a selfie with a TMK Santa #cowlebrity!
Time: 6 - 7:30pm
Address:
17670 Meinig Ave, Sandy, OR 97055
Phone: 503-668-5569
Celebrate the Season at Sandy's 3rd Annual Shortest Day Walkway! Join for a magical evening of adventure and holiday cheer! Embark on a festive scavenger hunt through this beautifully decorated park, with special stops at all of the City of Sandy’s departments. Discover hidden treasures and spread some holiday joy along the way! Don’t miss out on this enchanting night—grab your family and friends, and make some merry memories together!
Time: 4:30 - 7:30pm
Address:
11211 SE McLoughlin Blvd, Milwaukie, OR 97222
Milwaukie's Winter Solstice event, an annual celebration at Milwaukie Bay Park to view the Christmas Ships, enjoy the beer garden and purchase tasty treats and glowing toys. Warm by the bonfire or cozy up to one of the small barrel fires - The bonfire will burn bright and warm again this year along with six other smaller, more intimate fires, for you and your family to enjoy! Christmas Ships Parade has been a tradition since 1954 - At 4:30pm the combined fleet of Christmas Ships will leave Portland headed to Lake Oswego, arriving in Lake Oswego around 6pm. The ships will go as far as George Rogers Park, remaining in the area for a while before turning and heading back to Portland, which will provide a second opportunity to see them pass by Milwaukie Bay Park around 7pm.
Time: 6 - 8pm
Address:
10117 SE Sunnyside Rd, Ste J, Clackamas , OR 97015
The Winter Solstice marks the longest night and shortest day of the year, a time when the earth seems to pause before the return of the sun. This powerful moment is an invitation to honor both the darkness and the light within us, and to reflect on the cycle of renewal. This Winter Solstice Class offers a chance to slow down, reconnect, and align with the rhythms of nature during this sacred time. In this class, you will explore the deeper meanings of the Winter Solstice, with practices designed to help you release what no longer serves you and set intentions for the new cycle of growth ahead. Whether you’re seeking personal transformation, a deeper connection with nature, or simply a mindful moment to pause and reflect, this class offers tools for grounding, healing, clarity, and connection. Join in making alters, journaling, and forming your vision for the year to come!
Time: 6 - 8pm
Address:
503 Main St, Oregon City, OR 97045
Have a closet full of puzzles and looking for a new challenge? Only do puzzles once and then want to pass them along? Gifted a puzzle that doesn't interest you? White Rabbit has the event for you! Bring in up to five puzzles to White Rabbit and receive the equal number of puzzle coupons. Hang out for a while and work on puzzles in community.
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