The Best Holiday Events in Clackamas County (December 2025)

If your December calendar isn’t full yet, Clackamas County is happy to fix that for you. From twinkle-light walks to historic house tours and small-town parades, there’s a lot happening between now and the end of the year.

Here are 7 of the best holiday events in Clackamas County for 2025, running from now (December 4) through December 20. Most of the big county-wide events wrap up before Christmas, so if something catches your eye, add it to the calendar sooner rather than later.

1. Clackamas County Winter Fair & Holiday Market (Canby)

Dates & Time (2025)

• Fridays & Saturdays:

  • Dec 5–6, 12–13, 19–20

  • 5:00–9:00 PM​

Location

• Clackamas County Event Center (Fairgrounds), 694 NE 4th Ave, Canby, OR​

Cost

• Tickets typically range from free for very young children up to around $10 per person, depending on age and ticket type; check the official Winter Fair or ticketing page for exact current pricing.​

What it is
The Winter Fair turns the fairgrounds into a walk-through light show and holiday market, with over 200,000 lights, tunnels, a huge Christmas tree “show,” Santa visits, crafts for kids, vendors, and food and drinks.​

Why go

• It’s one of the biggest, most immersive holiday experiences in the county.

• Easy to make into a full night out: lights + Santa + snacks + local shopping.

• Perfect “bring the whole extended family and let everyone wander” kind of event.

2. Light Up The Night (Canby)

Date & Time (2025)

• Friday, December 5, 2025

• Parade begins at 6:00 PM; tree-lighting celebration at 6:30 PM​

Location

• Wait Park, corner of 3rd Ave & Grant St, Downtown Canby, OR​

Cost

• Free community event (bring a little cash if you want hot chocolate or treats from vendors).

What it is
Canby’s classic holiday kick-off: a lighted parade rolls through downtown and ends at Wait Park for the official tree lighting. Expect carolers, hot chocolate, Santa, and that small-town, shoulder-to-shoulder “we all know each other” energy.​

Why go

• Peak Hallmark-movie vibes, but the real-life version.

• Great for kids, grandparents, and anyone who likes parades and twinkle lights.

• An easy way to feel connected to the community if you’re new to town.

3. Operation Santa Claus Parades (Multiple Cities)

Hosted by Clackamas Fire District, this rolling parade brings Santa to neighborhoods across the county on fire engines and decorated apparatus.​

Parade Dates & Times (2025)
Each starts at 6:00 PM:​

• Thursday, December 4 – Oregon City

• Friday, December 5 – Happy Valley

• Thursday, December 11 – Milwaukie

• Friday, December 12 – Sandy

(Additional routes in Clackamas earlier in the week for anyone just outside the core cities.)​

Cost

• Free to watch.

• They also accept new, unwrapped toy donations at specific drop-off events on other dates/locations in early December (Hilltop Cinema in Oregon City, Happy Valley City Hall, Sandy Fire Station 71, Safeway Damascus, Milwaukie Farmer’s Market lot, etc.).​

What it is
Firefighters escort Santa through different neighborhoods on decorated rigs, with lights and sirens toned down to “festive,” not frightening. Kids can wave from their driveways; adults can enjoy the nostalgia and community feel.

Why go

• Zero logistics: you can often see it right from your block.

• A fun way to help support local toy drives and families in need.

• Pure, simple, hometown holiday joy.

4. Heritage Holidays (Historic Oregon City)

Date & Time (2025)

• Saturday, December 6, 2025

• Generally 10:00 AM–4:00 PM across participating sites​

Locations (Multiple Historic Sites)

• Baker Log Cabin & Pioneer Church – 18005 S Gronlund Rd, Oregon City

• Francis Ermatinger House – 619 6th St, Oregon City

• McLoughlin House & Barclay House – 713 Center St, Oregon City

• Stevens‑Crawford House – 603 6th St, Oregon City

• William L. Holmes House at the Rose Farm – 536 Holmes Ln, Oregon City​

Cost

• Free admission at all participating sites, with donations appreciated at some locations.​

What it is
On the first Saturday in December, Oregon City’s historic homes and museums go all‑in on holiday decor: open houses, period decorations, crafts, music, refreshments, and docents in costume sharing local history.​

Why go

• Feels like stepping into a Charles Dickens scene—but with Oregon City history.

• A great way to get to know the deeper roots of the area beyond modern development.

• Ideal for history buffs, kids who like “old-timey” things, and anyone who loves a cozy holiday afternoon walk between sites.

5. Downtown Oregon City Holiday Tree Lighting

Date & Time (2025)

• Saturday, December 6, 2025

• 5:00–7:00 PM​

Location

• Liberty Plaza, Main Street, downtown Oregon City, OR​

Cost

• Free community event.

What it is
Downtown Oregon City’s big holiday kickoff: tree‑lighting, festive music, Santa visits, and downtown businesses open so you can shop, sip, and stroll under the lights.​

Why go

• Easy to pair with dinner or drinks at places like Nebbiolo, Canard, or other Main Street spots.

• Perfect for those who like festive energy but don’t necessarily want a huge crowd or drive‑through display.

6. Winterfest & Community Tree Lighting (Wilsonville)

Date & Time (2025)

• Thursday, December 4, 2025

• Tree lighting at 5:00 PM; additional Winterfest activities typically follow in the park.​

Location

• Town Center Park, 29600 SW Park Pl, Wilsonville, OR​

Cost

• Free city event.

What it is
Wilsonville’s Winterfest brings the community together for the annual tree lighting, choirs, photos with Santa, kids’ crafts, and other activities in Town Center Park.​

Why go

• A great choice if you’re in Wilsonville, Charbonneau, or Aurora and want something close by.

• Very family‑friendly, stroller‑friendly, and easy to come and go as needed.

7. Christmas in Canby Ugly Sweater 5K

Date & Time (2025)

• Saturday, December 6, 2025

• 9:00 AM start time​

Location

• Canby, OR (race event based in town; check the registration page for the exact start line and course details).​

Cost

• 5K entry: $50 for adults

• Youth (ages 0–12): $30​

What it is
A festive 5K where ugly sweaters are strongly encouraged. It’s part fitness event, part holiday party—run, jog, or walk your way through Canby in full December costume and finish in time for more local holiday fun that afternoon.​

Why go

• Great excuse to get outside, even when the couch and cocoa are calling.

• Perfect for families, friend groups, or anyone who needs a little accountability to move their body between Thanksgiving and New Year’s.

Keeping it real (estate): How to actually use this list

December fills up quickly. Instead of trying to do everything, pick:

• One big light/market experience (Winter Fair in Canby),

• One community tree lighting/parade (Canby, Oregon City, or Wilsonville), and

• One “something different” (historic house tour or ugly sweater 5K).

That way you get lights, community, and a story you’ll still be telling in January—without scheduling yourself into exhaustion.

If you’re thinking about a move in 2026 and want to use these events as a way to “test drive” different towns in Clackamas County, you’re already thinking like a local. Go experience them in person—and if you’d like a calm, honest conversation about what it might look like to buy in any of these areas, you can always schedule a 30‑minute intro call or connect with me here.

Keeping it real (estate), even during the holiday chaos.