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Mark Your Calendars for These Winter Events

The best events in Central Oregon this winter that you don’t want to miss.

Oregon WinterFest. Photo by Brian Becker courtesy of Lay It Out Events.

Winter is a wonderful time to be in Central Oregon. There’s (hopefully) some snow on the ground and the sun still shines, brining crisp and light days to enjoy outside. There’s also a host of events around the region that everyone in the family can enjoy. From holiday events and parades to musicals and festivals, these are the events that you don’t want to miss in Central Oregon this winter.

Note: This list will be updated as more events are announced and dates are confirmed, so check back throughout the fall for the latest information.


Holiday Food & Gift Festival
November 16-18

This is the nineteenth year for the Holiday Food & Gift Festival, an expo with hundreds of vendors and thousands of attendees. Browse handmade art, jewelry, textiles, toys and more, as well as artisan and gourmet food products. It’s a great place to support local businesses when you buy gifts this holiday season.

Grand Illumination
November 17

Between the petting zoo, train rides, meeting Santa in the North Pole and watching the tree lighting ceremony, there are plenty of activities to keep families busy at Sunriver’s twentieth annual Grand Illumination. The festivities begin at noon, and Santa will be available to visit intermittently between activities.

Sisters Holiday Celebration and Parade
November 23-24

The Sisters Holiday Celebration and Parade takes over the whole town for the weekend. On Friday, don’t miss the tree lighting at 5:30 p.m. in Fir Street Park in Sisters. And on Saturday at 2 p.m., the streets of downtown Sisters will be taken over by the Christmas parade. After, kids can visit Santa at the Christmas Village.

Starlight Christmas Parade
November 24

In Redmond, Christmas kicks off just days after the turkey’s been carved with the Starlight Christmas Parade. Grab your spot on the street before sundown to watch the parade, then stick around for the Christmas tree lighting.

Community Christmas Tree Lighting
November 30

Bundle up in a puffy coast, stocking cap and gloves and kick off the holiday season in Bend with the Christmas Tree Lighting at Drake Park in downtown Bend. Carolers will be singing until Santa arrives and the tree is lit at 6:59 p.m.


Bend Christmas Parade
December 1

Runners dressed up in holiday gear and jingle bells on their shoes take part in a 5k walk or run through downtown Bend to lead off the Christmas Parade. It’s an annual tradition that draws crowds to downtown on a chilly December morning. Make sure you bring some hot cocoa to watch the parade that officially takes off at noon.

Central Oregon Winter Beer Festival
December 8

GoodLife‘s annual Central Oregon Winter Beer Festival returns for the sixth year. From 2 to 9 p.m., stop by the brewery to taste the latest brews from more than twenty craft breweries. A $15 admission gets you a tasting mug and five drink tokens. The event is a fundraiser for the Central Oregon Brewers Guild.

Holiday Lights Winter Paddle Parade
December 14

Each year, paddlers decorate their kayaks, canoes and paddleboards for the Holiday Lights Winter Paddle Parade on the Deschutes River. Those that want to participate should go to Tumalo Creek Kayak & Canoe in the afternoon, but those that just want to watch only have to wait until sunset and gather around the river at the Old Mill District to take in this annual tradition.


West Side Story
January 25-February 2

Don’t miss out on getting tickets to one of the greatest love stories of the 20th century. Thoroughly Modern Productions will stage the classic musical “West Side Story” at the Tower Theatre in January and February with a cast of talented local performers.


Oregon WinterFest
February 15-17

Oregon WinterFest is a three-day event packed with enough music, activities, food, drinks and fun for families to keep you busy all weekend. There’s the 10 Barrel Rail Jam, 5k and 10k races, ice sculpting competitions, concerts each night, and of course the best local food and drinks to keep you fueled for it all.

Eagle Watch
February 22-23

Each year, bald eagles and more birds of prey take the spotlight at Cove Palisades State Park in Madras. Eagle Watch has activities for kids and families all weekend to celebrate the birds, including live birds of prey onsite and educational activities to join. The Quartz Creek Drummers and Dancers will also perform.

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