Facebook
X
Pinterest
Copy Link
Licensed Oregon broker, and a local for more than 30 years (I moved here when I was two). I’ve stood through most of these in the cold at least once.
Right around Thanksgiving weekend, Central Oregon basically flips a switch. One Saturday it’s quiet, and the next there are lit floats rolling down Main Street and Santa landing by helicopter in the Old Mill.
I’ve lived here a long time and I still plan my late-November weekends around this stuff. Part of the fun is that every town does it a little differently. Redmond runs its parade after dark. Sisters keeps it small and walkable. Bend spreads it across two weeks.
Here’s what’s actually happening this year, with the dates I could confirm, plus the honest stuff about doing any of it with kids in 25-degree weather.
The short version
- Sunriver starts early with its Grand Illumination on Saturday, November 21.
- The big weekend is right after Thanksgiving. Sisters Holiday Palooza and Redmond’s Starlight Parade both land on Saturday, November 28.
- The Bend Christmas Parade is Saturday, December 5 at noon downtown, and SantaLand runs most weekends in the Old Mill.
- La Pine, Prineville, and Madras have their own parades and lightings. Confirm those dates with the local organizers.
- Dates move for weather. Check the day before.
When does the Central Oregon holiday season actually start?
The short answer is the weekend after Thanksgiving. Thanksgiving is Thursday, November 26 this year, and by that Friday and Saturday most towns have their lights on.
The one that jumps the line is Sunriver. The Grand Illumination at Sunriver Resort is set for Saturday, November 21, from noon to 7pm at The Lodge. They list the date as subject to change, so confirm it before you drive out. If you want the first real dose of holiday Central Oregon, that’s your earliest shot.
Where are the tree lightings and parades in Bend this year?
Bend spreads its holiday events across the Old Mill District and downtown.
- Fri, Nov 27 Santa flies into the Old Mill by AirLink helicopter at 10am. It’s quick (10 to 10:30), but it’s a fun one for little kids.
- Nov 27 to Dec 21 SantaLand in the Old Mill runs November 27, 28, and 29, then most Friday through Sunday dates in December (the 4th through 6th, 11th through 13th, and 18th through 21st), 11am to 5pm.
- Sat, Dec 5 The Bend Christmas Parade steps off at noon. The route starts near Harmon Boulevard, heads down Newport Avenue, along Wall Street, onto Franklin Avenue, and ends near Riverside by Drake Park.
- Sun, Dec 6 Chabad of Central Oregon lights the menorah in the Old Mill from 4 to 6pm.
The one I can’t give you a firm date for yet is the downtown community tree lighting at Brandis Square. It’s an early-December tradition the Downtown Bend Business Association puts on, but the 2026 date wasn’t posted when I wrote this. Check with them before you count on it.
What’s happening in Redmond, Sisters, and Sunriver?
This is where the weekend after Thanksgiving gets busy, because three of the best ones overlap.
- Redmond Starlight Parade. Sat, Nov 28, 5pm It starts on 6th Street in downtown Redmond. It runs after dark on purpose, so every float is lit. It’s one of the better parades in the region and worth the drive if you’re coming from Bend.
- Sisters Holiday Palooza. Sat, Nov 28, 3:30pm The parade runs down East Main Street and the party lands at Fir Street Park, wrapping up around 5:30. Since it’s earlier in the day than Redmond’s, you can technically do both if you plan the drive.
- Black Butte Ranch tree lighting. Fri, Nov 27 The night before Palooza, Black Butte does a tree lighting with caroling and the Sisters High School jazz choir.
- Sunriver Grand Illumination. Sat, Nov 21 The early one, covered above, at Sunriver Resort.
What about La Pine, Prineville, and Madras?
These towns do the holidays too, and I’m not going to pretend I had every date locked down when I wrote this.
Prineville runs a lighted Christmas parade and a downtown tree lighting in early December most years. Madras holds its Christmas Lights Parade in December as well. La Pine’s happenings usually turn up on community pages closer to the date.
If you’re out that way, the Central Oregonian covers Prineville and the Madras Pioneer covers Jefferson County, and those are the two most reliable places to catch confirmed dates. I’d rather send you to the real source than put a wrong date on my own site.
The honest stuff nobody puts on the flyer
A few things worth knowing before you load everyone into the car:
It’s cold, and often icy. Most of these are outdoor and after dark in late November. Real layers, real boots, hand warmers in the pockets. I’ve learned this the hard way more than once.
Dates move. Organizers shift things for weather, and the posted date isn’t always the final one. I confirm the day before, every single time, and you should too.
Parking downtown Bend during the Christmas Parade is rough. There are road closures along the route. Park a few blocks out and walk in, or get there early.
You’re sharing the roads. Thanksgiving weekend means Black Friday traffic plus everyone driving over the passes. Give yourself more time than you think you need, especially if the passes are snowy.
Frequently asked questions
- When does the Central Oregon holiday season start in 2026?
- Most towns turn on the weekend after Thanksgiving. Thanksgiving is Thursday, November 26, 2026, and by that Friday and Saturday, November 27 and 28, Bend, Redmond, and Sisters all have events. Sunriver starts earliest with its Grand Illumination on Saturday, November 21.
- When is the Bend Christmas Parade in 2026?
- The Bend Christmas Parade is Saturday, December 5, 2026, at noon in downtown Bend. The route runs from near Harmon Boulevard down Newport Avenue, along Wall Street, onto Franklin Avenue, and ends near Riverside Boulevard by Drake Park.
- When is the Redmond Starlight Parade in 2026?
- The Redmond Starlight Parade is Saturday, November 28, 2026, at 5:00 PM, starting on 6th Street in downtown Redmond. It runs after dark so every float is lit.
- Is there a tree lighting in Sisters, Oregon?
- Yes. Sisters Holiday Palooza, with a parade down East Main Street and a tree lighting at Fir Street Park, is Saturday, November 28, 2026, from 3:30 to 5:30 PM. Black Butte Ranch also holds a tree lighting with caroling on Friday, November 27.
- What holiday events are in the Old Mill District in Bend?
- The Old Mill District hosts SantaLand on November 27, 28, and 29 and most Friday through Sunday dates in December, from 11 AM to 5 PM. Santa arrives by AirLink helicopter on Friday, November 27 at 10 AM, and Chabad of Central Oregon holds a menorah lighting on Sunday, December 6 from 4 to 6 PM.
- Do the dates for these events ever change?
- Yes. Organizers sometimes move holiday events for weather, and the Sunriver Grand Illumination date is officially listed as subject to change. Confirm any date with the organizer the day before, especially anything outdoors.
That’s the lineup I’ve got so far. If a date shifts or I hear about something new, I’ll keep this updated. And if you’re spending the season figuring out whether one of these towns might be home, I’m always happy to talk through what each one is actually like to live in, the honest version. No pressure, just real info. See you out there, probably in a parking lot wearing too many layers. 🏔️
