Windy Wonderland & Tree Lighting — Troutdale
Sat, Dec 5Dec 5 – Dec 6 · 12:00 PM – 7:00 PM · Saturday Dec. 5 and Sunday Dec. 6, 2026, 12–7 p.m.; tree lighting in Mayors Square just after 5 p.m. Sunday
The Troutdale House and Mayors Square, downtown Troutdale411 E Historic Columbia River Hwy, Troutdale, OR 97060Directions
All ages
No admission fee mentioned; hot cocoa at the lighting is free; donations for Snow Cap earn raffle tickets
Similar picks in Portland
Dec5SatTree lightingsSame daySat, Dec 5 · 4:00 PM
Sherwood Holiday Festival — Parade and Tree Lighting
Cannery Square Park, Old Town Sherwood
Free
Dec5SatTree lightingsSame daySat, Dec 5 · 4:30 PM
Milwaukie Umbrella Parade and Tree Lighting
Historic Milwaukie City Hall (parade from South Downtown Plaza)
- Tree lightings
Same daySat, Dec 5 · 5:00 PM
West Linn Annual Holiday Parade 2026 – "Light Up the Night" with Tree Lighting
Historic Willamette Main Street area (directions point: Willamette Fire Station, TVFR #59)
About this adventure
Troutdale's two-day holiday festival fills its historic downtown on the first weekend of December. A holiday market of local makers with music and seasonal treats runs inside The Troutdale House, and children can pick up a game card there for a hide-and-seek scavenger hunt: Harry, a Troutdale-born Sasquatch toy made by local toymaker Calou Shop, hides inside participating downtown businesses, and kids who collect every stamp return to the market for a free gift. Santa has a North Pole headquarters near the market for visits (photos are not printed on site; times to be announced). The weekend ends with the city's tree lighting in Mayors Square just after 5 p.m. on Sunday, December 6, with free hot cocoa and live holiday music before the live blue spruce is lit; the city advises arriving early. Bringing cash, food or clothing for Snow Cap Community Services earns a raffle ticket.
Loading organizer reviews…
Questions & tips
Ask other families about this activity or share a tip. Comments don’t count toward the organizer’s rating; for anything official, check with the organizer.
Loading comments…