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EVENTS

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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Chapel Theatre Play Festival
Chapel Theatre

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

Address: 4107 SE Harrison St, Milwaukie, OR 97222

This play festival showcases writers and their short plays by matching them up with local directors and actors to carry out their work. Playwrights submit their short plays to be considered while local directors and actors audition to take part in the festival. Chapel Theatre Co connects the plays with actors and directors and allows two weeks to rehearse before presenting the finished product.

Historic Walking Tours of Milwaukie
Historic Main Street area of Milwaukie

Time: 10am - 12pm

Join a local historian on a guided walk around the historic Main Street area of Milwaukie, Oregon! Tours happen rain or shine and will last about 2 hours and cover approximately 1.75 miles.

Sunset Snowshoe
White River West Trailhead/Sno Park

Time: 2:30pm - 6pm

Address: OR-35, Mt. Hood, OR 97041
Phone: (503) 359-2568

Produced By: Adventures Without Limits

Have you ever seen Mt. Hood transform into shades of pink and yellow as the sun sets on the mountain? Strap on your snowshoes and join Adventures Without Limits expert guides as they explore Mt. Hood National Forest and maybe catch the emergence of the full moon (depending on the weather!). This trip is open to all and is designed to be inclusive and acessible. No experience necessary, just a sense of adventure and a love for being outdoors! Transportation is available from a centralized pickup location

Timber to Ash
Toolbox Art Gallery

Time: 10am - 5pm

Address: 2029 SE Jefferson St, Milwaukie, OR 97222

Enjoy the works of Jason Tipps, professional tradesman and self-taught artist and Michael Rank, professional project manager and wood crafter. Their art is on display through February at the Toolbox Art Gallery which aims to bring creatives in the building industry together.

Chapel Theatre Play Festival
Chapel Theatre

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

Address: 4107 SE Harrison St, Milwaukie, OR 97222

This play festival showcases writers and their short plays by matching them up with local directors and actors to carry out their work. Playwrights submit their short plays to be considered while local directors and actors audition to take part in the festival. Chapel Theatre Co connects the plays with actors and directors and allows two weeks to rehearse before presenting the finished product.

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

Timber to Ash
Toolbox Art Gallery

Time: 10am - 5pm

Address: 2029 SE Jefferson St, Milwaukie, OR 97222

Enjoy the works of Jason Tipps, professional tradesman and self-taught artist and Michael Rank, professional project manager and wood crafter. Their art is on display through February at the Toolbox Art Gallery which aims to bring creatives in the building industry together.

Timber to Ash
Toolbox Art Gallery

Time: 10am - 5pm

Address: 2029 SE Jefferson St, Milwaukie, OR 97222

Enjoy the works of Jason Tipps, professional tradesman and self-taught artist and Michael Rank, professional project manager and wood crafter. Their art is on display through February at the Toolbox Art Gallery which aims to bring creatives in the building industry together.

Timber to Ash
Toolbox Art Gallery

Time: 10am - 5pm

Address: 2029 SE Jefferson St, Milwaukie, OR 97222

Enjoy the works of Jason Tipps, professional tradesman and self-taught artist and Michael Rank, professional project manager and wood crafter. Their art is on display through February at the Toolbox Art Gallery which aims to bring creatives in the building industry together.

Trivia Night
Portland Cider Taproom

Time: 7- 9pm

Address: 8925 SE Jannsen Rd, Bldg F, Clackamas, OR 97015

Join Portland Cider Company every Thursday night for a Trivia night with Geeks Who Drink. Free to play and prizes for first and second place along with a winner each round.

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Showing results 1 to 10 of 245

Chapel Theatre Play Festival
Chapel Theatre Play Festival
Saturday, Jan 31, 2026
Thurs - Sat 7:30pm, Sun 2pm
Chapel Theatre
4107 SE Harrison St, Milwaukie, OR 97222
Occurs: Every week on Sunday Thursday, Friday, Saturday, until February 01, 2026
This play festival showcases writers and their short plays by matching them up with local directors and actors to carry out their work. Playwrights submit their short plays to be...Read More
Historic Milwaukie Walking Tour
Historic Walking Tours of Milwaukie
Saturday, Jan 31, 2026
10am - 12pm
Admission: $10
Historic Main Street area of Milwaukie
Occurs: Every week on Saturday until January 31, 2026
Join a local historian on a guided walk around the historic Main Street area of Milwaukie, Oregon! Tours happen rain or shine and will last about 2 hours and cover...Read More
Three snowshoers smile for the camera while walking across a snowy meadow.
Sunset Snowshoe
Saturday, Jan 31, 2026
2:30pm - 6pm
Admission: $110
White River West Trailhead/Sno Park
OR-35, Mt. Hood, OR 97041
Produced By: Adventures Without Limits
Have you ever seen Mt. Hood transform into shades of pink and yellow as the sun sets on the mountain? Strap on your snowshoes and join Adventures Without Limits expert guides as they explore...Read More
Timber to Ash Art Exhibition
Timber to Ash
Saturday, Jan 31, 2026
10am - 5pm
Toolbox Art Gallery
2029 SE Jefferson St, Milwaukie, OR 97222
Occurs: Every week on Tuesday Wednesday, Thursday, Friday, Saturday, until February 28, 2026
Enjoy the works of Jason Tipps, professional tradesman and self-taught artist and Michael Rank, professional project manager and wood crafter. Their art is on display through February at the Toolbox...Read More
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