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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.

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Christmas Tree Farms and Festivals
Throughout Clackamas County

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.

Holiday Artists Marketplace
ARTspace Gallery

Time: Tu - Fri 10am-5pm, Sat 10am-2pm

Address: 380 A Street, Lake Oswego, OR 97068
Phone: 5032721214

Celebrate the Art of Giving with Lake Oswego traditional Holiday Marketplace, curated & hosted by the Arts Council! Arts Council of Lake Oswego celebrates the Art of Giving with local favorite annual show, Holiday Marketplace. Featuring fine art and handicrafts from 26 local artisans, Holiday Marketplace is your one-stop shop for unique & handmade gifts for your most hard-to-shop-for loved ones.

Miracle on 34th Street - Stage Play
Lakewood Center for the Arts

Time: Wed-Sat 7:30pm, Sun 2pm

Address: 368 S State St, Lake Oswego, OR 97034

Kris Kringle, an older man living in a retirement home, takes a job as Santa at Macy's. He spreads waves of goodwill by directing parents to other stores to find exactly the toy their child desires. Viewed as delusional by Macy's vocational counselor, Kris finds himself in a court competency hearing. The belief of one little girl in Santa is particularly at risk. This is a story where love, decency, and generosity of spirit are their own rewards.

Open Mic Night
Ale & Cider House

Time: 5:30 - 9:30pm

Address: 1720 Willamette Falls Drive, West Linn, OR 97068

Join the Ale & Cider House for weekly open mic nights. Sign-ups at the bar begin at 5:30pm and performances begin at 6:30pm. Once your name is on the list, you will get a 15-minute window to perform music, poetry, or comedy!

Sandy Winterfest
Meinig Memorial Park

Address: 17670 Meinig Ave, Sandy, OR 97055

Stroll through Meinig Park and take in all the lights and decorations. Lights will be on nightly. There will be vendors selling items on the following nights: December 6th, 13th, 21st, & 22nd.

Canby's Light Up The Night
Wait Park, Canby

Time: 6pm

Address: 350 N Grant St, Canby, OR 97013

Produced By: City of Canby

The 24th Annual Light Up The Night event will begin with a lighted parade throughout downtown Canby. The lighted parade will finish at Wait Park at approximately 6:30p as the Fire District delivers Santa and Mrs. Claus on N. Grant Street. The Oregon Trail Pitchpipers, a Barbershop Harmony Society musical group, will return with holiday songs to welcome Santa to the Wait Park Gazebo. Children of all ages are encouraged to stay for a chat and photo opportunity with Santa and Mrs. Claus. Santa will stay until the last child has the opportunity to share. Once the presenters are finished and Wait Park is lit up with holiday lights and cheer, the Willamette Valley Big Band- Canby's premier big band - will perform holiday music in Wait Park at approximately 7:00p

Christmas Tree Farms and Festivals
Throughout Clackamas County

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.

Estacada Christmas Tree Lighting
Harvest Market Square

Address: 280 N Broadway St, Estacada, OR 97023

Produced By: Downtown Estacada Commission

Mark your calendars for the Estacada Christmas Tree Lighting on the first Friday of December! Select businesses will be open later, so bundle up and head downtown to explore all the charming shops and restaurants. Enjoy festive music, twinkling lights, vendors, Santa visits and more!

Holiday Artists Marketplace
ARTspace Gallery

Time: Tu - Fri 10am-5pm, Sat 10am-2pm

Address: 380 A Street, Lake Oswego, OR 97068
Phone: 5032721214

Celebrate the Art of Giving with Lake Oswego traditional Holiday Marketplace, curated & hosted by the Arts Council! Arts Council of Lake Oswego celebrates the Art of Giving with local favorite annual show, Holiday Marketplace. Featuring fine art and handicrafts from 26 local artisans, Holiday Marketplace is your one-stop shop for unique & handmade gifts for your most hard-to-shop-for loved ones.

Miracle on 34th Street - Stage Play
Lakewood Center for the Arts

Time: Wed-Sat 7:30pm, Sun 2pm

Address: 368 S State St, Lake Oswego, OR 97034

Kris Kringle, an older man living in a retirement home, takes a job as Santa at Macy's. He spreads waves of goodwill by directing parents to other stores to find exactly the toy their child desires. Viewed as delusional by Macy's vocational counselor, Kris finds himself in a court competency hearing. The belief of one little girl in Santa is particularly at risk. This is a story where love, decency, and generosity of spirit are their own rewards.

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Timberline Mountain Guides, Inc
Women's Ski Mountaineering Camp
Friday, May 15, 2026
Timberline Mountain Guides, Inc
Mt Hood, OR
Occurs: Every day until May 18, 2026
This Women’s Ski Mountaineering Camp is an opportunity for experienced backcountry skiers and splitboarders to connect and build community while learning advanced ski touring and ski mountaineering skills in a...Read More
cedar benches, lounge chairs and house plants are lit up by sun in the front room of Sauna Glo.
LGBTQIA+ Sauna Social
Thursday, May 21, 2026
5 - 8pm
SaunaGlo
1915 SE Jefferson St, Milwaukie, OR 97222
Occurs: The Third Thursday of every 1 month(s) until June 18, 2026
Come build community, and gather together with LGBTQIA+ identified folks during this intentional queer-only sauna social. Join SaunaGlo in a safe space to sweat, plunge and connect with a friend, or...Read More
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