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Central Oregon Weekend Planner – Dec. 20-22, 2019

Central Oregon Weekend Planner – Dec 20-22, 2019.

Here is our Central Oregon weekend planner, created each week to showcase events throughout Central Oregon!


Friday, Dec. 20

Winter Solstice Celebration @ The Pavilion, Bend

  • FRICelebrate the shortest day of the year with a Winter Solstice Celebration. With festivities to welcome winter’s delights, ice skaters who bring a canned food item to donate to NeighborImpact will enjoy a special $6 admission price including skate rental. It’s a wonderful party with lots of treats, smiles and a performance from Bend Ice Figure Skating Club.

Christmas In The Pines @ Crook County Fair Grounds

  • FRI-SATChristmas in the Pines has become a Prineville tradition. It is a beautiful drive thru Christmas light display. We offer an electrifying event full of family fun and enrichment at the Crook County Fairgrounds. Entrance by donation of food or money. Every Saturday night, there will be a live nativity as well as Santa and Mrs. Claus so come enjoy cookies and hot chocolate with them!

Journey  To Bethlehem @ the Tower Theater

  • FRI-SUNJourney back to the sights, sounds and smells of the very 1st Christmas Eve in the bustling town of Bethlehem! This FREE, live-action walk-through experience with over 100 actors and live animals is quickly becoming one of Central Oregon’s best Christmas traditions!

Swingin’ Tower Christmas @ the Tower Theater

  • FRI-SUNBend’s family-friendly holiday tradition returns with more “cool yule” stories and songs backed by Jim Tennant’s 18-piece live big band. Host Mollie Tennant (“Cats,” “Mamma Mia,” “Les Miz”) welcomes special guests Heather Salvesen, Gary Fulkerson, Bob Shaw, Alastair Jaques, plus the return of Olive the Elf and jolly ol’ St. Nick.


Saturday, Dec. 21

Bingo Blitz: Gift Wrapped Edition @ Worthy Brewing

  • SATBingo Blitz is Bend’s Best FUNdraiser! This is Bingo 2.0, giving back to our community while giving more to our guests. Bingo Blitz is four rounds of high energy bingo played in 90 minutes, stuffed with prizes & surprises, live entertainment, a half time show and always something a lil’ extra!

Redmond’s Holiday Village in Centennial Park

  • SAT – Find original gifts for the hard-to-buy-for friend, family member, or co-worker at Redmond’s Holiday Village Market, presented by the Redmond Chamber of Commerce @ CVB. Held on four Saturdays throughout the holiday season, the Holiday Village Market features vendors selling local arts, crafts, and artisan goods from old-world-styled kiosks and vendor spaces within Redmond Centennial Park.

Roast of 2019 @ 10 Barrel Eastside, Bend

  • SAT – The 4th annual End of Year Roast! This tradition started in 2016 because that year sucked. Every year since has said “Hold My Beer.” 2019 was not to be undone. Come down and watch local comedians and special guests talk sh*t about a year that has managed to bend everyone over. Why lie, there will be a lot of roasting each other, too. Please wear your cocktail attire. Or don’t. Let’s be honest, after a year like this, no one is going to blame you for wearing sweats. We won’t impeach you for it.


Sunday, Dec. 22

Menorah Lighting in the Old Mill District’s Center Plaza

  • SUN – Celebrate Chanukah this year with the annual menorah lighting in the Old Mill District’s Center Plaza on Sunday, Dec. 22. Presented by the Chabad of Central Oregon, this year’s ceremony will start at 4:30 p.m. A chocolate coin drop, hot drinks, potato latkes, and Chanukah music are all part of the festivities. All faiths and denominations are welcome!


Tuesday, Dec. 24, Christmas Eve

A Holiday Eve With Han Oak’s House Of Prime Rib @ The Suttle Lodge

  • TUE Super-talented chef Peter Cho of Portland’s famed Han Oak is bringing the family to the Suttle Lodge for Christmas, and you’re invited. On Christmas Eve, Cho will cook a Prime Rib dinner, Korean-style, with dumplings, dessert and more. Bring the kids and gather around the fire in the lodge for an unforgettable holiday feast!

Brunch With Santa @ The Great Hall, Sunriver

  • TUEHave brunch with Santa and all of his Sunriver friends in the beautiful and historic Great Hall at Sunriver Resort. Enjoy a festive spread of holiday favorites and fun holiday characters to mix and mingle with too! Reservations are required / 36-hour cancellation policy/ credit card hold. Call (541) 593-1000 for reservations.

Christmas Eve Brunch & Dinner @ Brasada Ranch

Wednesday, Dec. 25, Christmas Day

Christmas Eve Brunch & Dinner @ Brasada Ranch

  • WED The Ranch House will be decorated for the season and will offer an a la carte menu for Christmas Dinner. Enjoy a full buffet dinner with a handcrafted holiday menu from Chef Doug. Enjoy the holiday decorations and incredible views. Please call (541) 526-6870 for reservations.

Christmas Dinner Buffet @ 10 Below At The Oxford Hotel, Bend

  • WED Join us for Christmas Dinner! Our special buffet menu includes a variety of decadent starters, entrees, and desserts to choose from. Dinner will be served from 1:30 pm to 7:30 pm, with Georges Bouhey performing jazz piano from 3:00 pm to 6:00 pm. Bouhey will also be performing on Christmas Eve from 5:00 pm to 8:00 pm.

Christmas Dinner @ The Great Hall, Sunriver

  • WED Dine like royalty during our spectacular Christmas Dinner at the historic Great Hall! Reservations are required / 36-hour cancellation policy/ credit card hold. Call (541) 593-1000 for reservations.



Gingerbread Junction @ Sunriver Lodge

  • Through Jan. 4Come visit Gingerbread Junction and marvel at the candy and cookie creations! Gingerbread Junction will open on Friday, Dec. 6th and gingerbread houses will be on display in the Sunriver Resort Main Lodge through Saturday, January 4th. Free and open to the public.

Holiday Light Show @ Sunriver Resort

  • Through Jan. 24 – Grab a Hot Toddy or Hot Cocoa at The Lodge and join us in the Back Yard for our NEW Holiday Light Show, happening 3 times every evening. Enjoy your favorite holiday songs as thousands of lights dance to the beat. Shows will be between 15 and 20 minutes long and will rotate through a selection of songs with a mix of kids and adult favorites.

Tubing Hill @ the Sunriver Homeowners Aquatics & Recreation Center (SHARC)

BendBroadBand’s Jazz At The Oxford

Live Music

  • ONGOING – The Volcanic Theatre and Pub hosts live music that’ll move you. Check their calendar for live theatre and movies as well!

A Starry Night At The Observatory

  • ONGOING – Come to the Oregon Observatory at Sunriver at night and view a guided constellation tour with experts.


Currently Playing Movies

Click here for most movie times/theaters OR choose from the following:


For a more comprehensive list of local events, check out the event calendars maintained by following:
The Source Weekly | Hack Bend | My Central Oregon | Visit Central Oregon | Visit Bend

The local chambers of commerce maintain event calendars as well:
Bend | La Pine | Madras | Prineville | Redmond | Sisters |

As do some of the larger resorts:
Black Butte Ranch (see “Event Calendar” @ top of page) | Brasada Ranch | Pronghorn | Sunriver

For events elsewhere in Oregon, head to Travel Oregon’s Event Calendar.


Click here to view this weekend’s open houses!

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Mitch Darby

I am a real estate broker, architect (both licensed in the State of Oregon), and life-long Oregonian. If you are looking to buy or sell, I can help! I have Northwest Knowledge and am proud to be associated with Berkshire Hathaway HomeServices - Real Estate's Forever Brand!

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