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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.

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.

Santa on The Farm
Triskelee Farm

Time: 10am - 2pm

Address: 29700 SW Mountain Rd, West Linn, OR 97068

Come join Triskelee for a jolly good time on the Farm! Santa will be spreading holiday cheer with his helping farm animals. Bring the whole family for a festive day filled with fun , delicious treats, and of course, a chance to meet the man in red himself. Don't forget to bring your camera to capture the magical moments. Santa will be out from 10:30-1:30pm. Visitors can partake in other activities from 10am-2pm. Everything will be undercover! Access to the bounce house included. Adults and carried babies are free to walk around. If adults want a photo there is a $5 add on. You do not need a ticket if you are not sitting with Santa or not partaking in the activities. You can take your own photos. About Activities will include: 1 Picture with Santa Bounce house Corn playing More Info: All activities will be in a covered area, however please be prepared for colder temperatures. Children must be attended by an adult at all times. Our food truck will be grilling from 10-2pm

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.

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.

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.

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.

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.

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Showing results 1 to 10 of 60

Lighted decorated Christmas Tree in Field
Christmas Tree Farms and Festivals
Sunday, Dec 14, 2025
Throughout Clackamas County
Occurs: Every day until December 24, 2025
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...Read More
Sandy Winterfest
Sandy Winterfest
Sunday, Dec 14, 2025
Admission: Free
Meinig Memorial Park
17670 Meinig Ave, Sandy, OR 97055
Occurs: Every day until January 04, 2026
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,...Read More
Santa on The Farm
Sunday, Dec 14, 2025
10am - 2pm
Triskelee Farm
29700 SW Mountain Rd, West Linn, OR 97068
Occurs: Every week on Sunday Saturday, until December 21, 2025
Come join Triskelee for a jolly good time on the Farm! Santa will be spreading holiday cheer with his helping farm animals. Bring the whole family for a festive day...Read More
ArtSpace Gallery Holiday Market
Holiday Artists Marketplace
Tuesday, Dec 16, 2025
Tu - Fri 10am-5pm, Sat 10am-2pm
Admission: Free
ARTspace Gallery
380 A Street, Lake Oswego, OR 97068
Occurs: Every week on Tuesday Wednesday, Thursday, Friday, Saturday, until December 24, 2025
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...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, Dec 18, 2025
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
A modern white building with large windows overlooks lush green vineyards under a soft sunset sky, surrounded by tall trees.
Piano Men: Remastered
Friday, Dec 19, 2025
7 - 10pm
Admission: $25-75
Festive Hill Winery
20100 SW Johnson Rd, West Linn, OR 97223
Produced By: Festive Hill Winery
18 year old pianist/singer, Hansen Berrett was Festive Hill's debut diner show performer, and by all accounts (and the fact that it sold-out), the night was a success. Hansen will...Read More
Shortest Day Walkway Sandy
Shortest Day Walkway
Friday, Dec 19, 2025
6 - 7:30pm
Admission: Free
Meinig Memorial Park
17670 Meinig Ave, Sandy, OR 97055
Join Sandy for a scavenger hunt through the lit up park. City Departments will be on site to share information, answer questions, and hand out goodies. ...Read More
Mini Highland Cow dressed up in a Santa suit at TMK Creamery
Selfies with Santa Cow
Saturday, Dec 20, 2025
1 - 2pm
Admission: $10/Family
TMK Creamery
27221 S Dryland Rd, Canby, OR 97013
Occurs: Every week on Saturday until December 20, 2025
Visit Santa Cow! Bring your kids, your crew or just your Christmas cheer and snap a selfie with a TMK Santa #cowlebrity!...Read More
Stocking Stroll through downtown Sandy
Stocking Stroll through downtown Sandy
Saturday, Dec 20, 2025
4 - 6pm
Admission: Free
Downtown Sandy
Downtown Businesses, Sandy,
Local downtown businesses will be participating. Stroll through downtown Sandy to get your stocking filled with treats and check out all the decorated businesses! ...Read More
Triskelee holiday Market
Triskelee Farm Holiday Market
Saturday, Dec 20, 2025
10am - 3pm
Admission: Free
Triskelee Farm
29700 SW Mountain Rd, West Linn, OR 97068
Join Triskelee Farm for their holiday market and enjoy tasty farm to table food, drinks, a local products! Walk the farm and see our ostrich, alpacas, and more! Free admission, kids...Read More
West Linn Santacon
West Linn Santacon
Saturday, Dec 20, 2025
5 - 8pm
Willamette Garage Pub + Food Carts
1590 Willamette Falls Drive , West Linn, OR 97068
West Linn’s jolliest night of the year is back! The Santa Pub Crawl kicks off at 5 PM December 20th. Gather your elves, fluff up those beards, and get ready...Read More
overhead view of a decorated Christmas tree and fireplace at Timberline Lodge
Christmas Eve at Timberline
Wednesday, Dec 24, 2025
2 - 6pm
Admission: $55 - 110
Timberline Lodge
27500 E Timberline Rd, Government Camp, OR 97028
The lodge is decorated for the Christmas holidays with a 30’ tree, garland, and lights. Enjoy Christmas Eve dinner in the Cascade Dining Room or around the grand fireplace. Other...Read More
A bright red cherry statue sits in bushes of green
Bing in the New Year
Wednesday, Dec 31, 2025
6-9 pm
Admission: Free
Downtown Milwaukie - Main & Harrison streets
10723 SE Main St., Milwaukie, OR 97222
Produced By: Milwaukie Arts Committee
The third annual Bing in the New Year celebration, presented by 1847 Food Park, will take place in downtown Milwaukie: The birthplace of the Bing cherry. This free, family-friendly outdoor event...Read More
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