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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.

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.

Peppermint Bear Asks Witch Way To Christmas?
Lakewood Center for the Arts

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

The Peppermint Bear show is a classic at Lakewood Theatre Company and it’s perfect for families and full of holiday cheer. Each year a new 45-minute episode is presented. A light continental breakfast with rolls, muffins, donuts, fruit etc and juice, and coffee is provided. It’s a show that is perfect for ages 3-103.

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

St. Josef's Winery Second Sunday Music - The Holiday Sing Along
St. Josef's Winery

Time: 12 - 5pm

Address: 28836 S Barlow Rd, Canby, OR 97013

Join St. Josef's for great wines, music and light bites inside our cozy tasting room. Natural Wines grown & made by Oregon Wine Pioneers. No cover charge. Call ahead or email info@stjosefswinery.com to reserve your table.

Wood-Fired Sauna Pop-Up
SaunaGlo

Time: 2 - 8pm

Address: 1915 SE Jefferson St, Milwaukie, OR 97222
Phone: (503) 445-7495

Come experience the magic of a traditional wood-fired sauna at SaunaGlo! For a limited time only, this pop-up features a beautiful mobile sauna open for reservations on Friday, Saturday and Sundays from 2-8pm. Includes cold plunge and botanical lounge!

Yoga at the Winery
Festive Hill Winery

Time: 9:00, 10:30

Address: 20100 SW Johnson Rd, West Linn, OR, USA, OR 97068
Phone: 5037075204

Produced By: Festive Hill Winery

connect mind and body while surrounded by the natural beauty and inviting atmosphere of the vineyard. Through thoughtfully guided classes, we will weave in themes of nature, equanimity, and joyful connection. The two classes we are offering: Vineyard Vinyasa: Sundays 9 - 10 am ($20 / class) Start your Sunday with a refreshing and grounding Vinyasa flow set against the stunning backdrop of the vineyard. This energizing morning class is designed to awaken the body and mind as we move through a mindful sequence of breath and movement, surrounded by the beauty of the vines. Whether you're a seasoned yogi or new to the mat, this all-levels flow invites you to connect with nature and enjoy a peaceful start to your day. Elévé Yogalates: Sundays 10:30-11:30 am ($20 / class) Ease into your Sunday with a refreshing blend of strength and stretch in this Yoga-lates class, where the mindful flow of yoga meets the core-toning power of Pilates. Set against the peaceful backdrop of the vine

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.

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Showing results 1 to 10 of 186

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
Miracle on 34th Street - lakewood theatre
Miracle on 34th Street - Stage Play
Sunday, Dec 14, 2025
Wed-Sat 7:30pm, Sun 2pm
Admission: $30+
Lakewood Center for the Arts
368 S State St, Lake Oswego, OR 97034
Occurs: Every week on Sunday Thursday, Friday, Saturday, until December 14, 2025
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...Read More
Peppermint Bear Asks Witch Way To Christmas
Peppermint Bear Asks Witch Way To Christmas?
Sunday, Dec 14, 2025
Admission: $17+
Lakewood Center for the Arts
368 S State St, Lake Oswego, OR 97034
Occurs: Every week on Sunday Saturday, until December 21, 2025
The Peppermint Bear show is a classic at Lakewood Theatre Company and it’s perfect for families and full of holiday cheer. Each year a new 45-minute episode is presented. A...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
St. Josef's Winery's Bavarian tasting room exterior lit at night with the entrance door open showing the staircase inside
St. Josef's Winery Second Sunday Music - The Holiday Sing Along
Sunday, Dec 14, 2025
12 - 5pm
Admission: Free
St. Josef's Winery
28836 S Barlow Rd, Canby, OR 97013
Join St. Josef's for great wines, music and light bites inside our cozy tasting room. Natural Wines grown & made by Oregon Wine Pioneers. No cover charge. Call ahead or...Read More
Wood-Fired Sauna Pop-Up
Sunday, Dec 14, 2025
2 - 8pm
Admission: $49
SaunaGlo
1915 SE Jefferson St, Milwaukie, OR 97222
Occurs: Every week on Sunday Friday, Saturday, until December 21, 2025
Come experience the magic of a traditional wood-fired sauna at SaunaGlo! For a limited time only, this pop-up features a beautiful mobile sauna open for reservations on Friday, Saturday and...Read More
A modern building with a tiled roof features a spacious terrace adorned with red umbrellas, set against a clear blue sky.
Yoga at the Winery
Sunday, Dec 14, 2025
9:00, 10:30
Admission: $20
Festive Hill Winery
20100 SW Johnson Rd, West Linn, OR, USA, OR 97068
Produced By: Festive Hill Winery
Occurs: Every week on Sunday until March 01, 2026
connect mind and body while surrounded by the natural beauty and inviting atmosphere of the vineyard. Through thoughtfully guided classes, we will weave in themes of nature, equanimity, and joyful connection. The...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
Open Mic Night at Ale & Cider House
Open Mic Night
Thursday, Dec 18, 2025
5:30 - 9:30pm
Admission: Free
Ale & Cider House
1720 Willamette Falls Drive, West Linn, OR 97068
Occurs: Every week on Thursday until January 29, 2026
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,...Read More
Image of textured oil paints with Third Thursday written over it.
Third Thursday
Thursday, Dec 18, 2025
4 - 6pm
Admission: Free
Downtown Lake Oswego
Lake Oswego, OR 97034
Produced By: Lake Oswego Chamber of Commerce
Occurs: The Third Thursday of every 1 month(s) until December 18, 2025
Enjoy Lake Oswego's downtown from every Third Thursday for business specials, music, art demonstrations, appetizers and wine at select businesses. Experience the easy walkability and the availability of casual to...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
Sea Glass Tree making class
Sea Glass Tree making class
Friday, Dec 19, 2025
2 - 3:30pm
Admission: $40
Red Chair Farm
27215 S Gribble Rd, Canby, OR 97013
Occurs: Every day until December 20, 2025
No crafty experience is necessary. Instructors will help you create this charming tree for your own home, showing you how to lay your glass to make it look like a...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
5 Blue Herons sit in nests in a tree
Maddax Woods Monthly Restoration
Saturday, Dec 20, 2025
9am - 12pm
Admission: Free
Maddax Woods
5785 River St, West Linn, OR 97068
Produced By: Friends of Maddax Woods
Occurs: The Third Saturday of every 1 month(s) until December 20, 2025
Families are welcome to help the Friends of Maddax Woods clean the trails and garden areas in the park. Make this a monthly tradition! Feel free to join for a...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
Holiday Solstice Dinner & Concert
Sunday, Dec 21, 2025
6-9pm
Admission: $60
St. Josef's Winery
28836 S Barlow Rd, Canby, OR 97013
St Josef's annual Holiday Concert Show & Dinner. A beautiful and festive night to share. Featuring music by the fabulous Michele Van Kleef & friends plus Beautiful Buffet by Chef Rudy-...Read More
Winter Solstice In The Farest
Winter Solstice In The Farest
Sunday, Dec 21, 2025
2pm
Admission: Free
Scrumpy Farest
Sandy, OR 97055
Join Scrumpy Farest for an open farm party celebrating the Winter Solstice! Cozy up in the shop with a cup of tea, or run wild in the fields. Hang out...Read More
Stronger Stake Park LGBTQ+ Camp
Winter Break Skateboard & Roller Skate Camp
Monday, Dec 22, 2025
9am - 12:30pm
Stronger Skatepark
6102 SE King Rd, Milwaukie , OR 97222
Occurs: Every week on Monday Tuesday, Friday, until December 26, 2025
This 3 half-day Winter Break Skateboard & Roller Skate Camp is open to all ages of kids with all experience levels. Join Stronger Skatepark for fun, games and activities....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
Last Thursday
Thursday, Dec 25, 2025
4 - 6pm
Admission: Free
Downtown Oregon City
Main Street, Oregon City, OR 97045
Occurs: The Last Thursday of every 1 month(s) until December 25, 2025
Oregon City's "Last Thursday" event series is an event designed to foster community engagement, support local businesses, and promote local activation. Participating retailers keep their doors open a bit later...Read More
A Despicable Christmas musical
A Despicable Christmas - Musical Theatre Camp
Monday, Dec 29, 2025
10am - 2pm
Admission: $200

716 Taylor Street, Oregon City, OR 97045
Produced By: Oregon City Children's Theatre
Occurs: Every day until January 02, 2026
Calling all young performers! Join for this one-week musical theatre camp where kids of all experience levels can dive into the world of stage performance. In just one week, instructors...Read More
Ramps and rails fill a large open space at Stronger Indoor Skatepark. A retro rainbow of blue, green, yellow & orange is painted along the wall.
Winter Break Camp - Skateboard
Monday, Dec 29, 2025
9am - 12:30pm
Stronger Skatepark
6102 SE King Rd, Milwaukie , OR 97222
Occurs: Every day until December 31, 2025
This 3 half-day Winter Break Skateboard Camp is open to all ages of kids with all experience levels. Join Stronger Skatepark for fun, games and activities....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
Family Friendly (Early) New Years Eve Bash at Dave & Buster's
Wednesday, Dec 31, 2025
4 - 7pm
Admission: $33.79
Dave & Buster's
11860 SE 82nd Ave, Happy Valley, OR 97086
Ring in the 2026 New Year with a celebration the whole family will love! Join Dave & Busters for an unforgettable Family New Year’s Experience packed with fun, games, food,...Read More
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