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Central Oregon Weekend Planner – Dec. 13-15, 2019

Central Oregon Weekend Planner – Dec 13-15, 2019.

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


Friday, Dec. 13

Après Ski Bash @ The Commons, Bend

  • FRIAnother Winter approaches, and another truly fantastic lineup of Free Monthly Friday Concerts is revealed and again, it’s aim is clear; to satisfy your body & soul! As always, these concerts are 100% free, all ages are most welcome.

Annual Holiday Lights Winter Paddle Parade @ Tumalo Creek Kayak & Canoe

  • FRIEvery year Bend’s most ded­i­cated paddling enthusiasts dress up their canoes and kayaks in bright lights and hol­i­day garb and pad­dle around the Deschutes River for a few hours for Tumalo Creek Kayak & Canoe’s Holiday Lights Winter Paddle Parade in the Old Mill Dis­trict. This is one of those events that gets the whole town in the spirit and feels very authen­tic to Bend.

Dirksen Derby @ Mt. Bachelor

  • FRI-SUNThe Dirksen Derby Rally Race is a snowboard and sit-ski race at Mt. Bachelor, Oregon. The actual location of the course changes every year based on snow conditions, terrain access, and variety. The two courses are top to bottom 100% hand dug.

Fiddler On The Roof @ Pinckney Center for The Arts

  • FRI-SUN – Set in the little village of Anatevka, Fiddler on the Roof centers on Tevye, a poor milkman, and his five daughters. With the help of a colorful and tight-knit Jewish community, Tevye tries to protect his daughters and instill them with traditional values in the face of changing social mores and the growing anti-Semitism of Czarist Russia. Rich in historical and ethnic detail, and featuring iconic and beloved songs such as “Sunrise, Sunset,” “If I Were a Rich Man” and “Matchmaker, Matchmaker,” Fiddler On The Roof, has won nine Tony Awards since its 1964 debut, and become a core staple of the musical theatre canon.

Journey to Bethlehem @ Bend Adventist Church

  • 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! Doors open each evening 30 minutes before the first Journey begins. Tickets are FREE, and although we expect that online reservations will fill up quickly, there will still be plenty of walk-in tickets available at the door. Enjoy seasonal music by local musicians while you wait for your journey.

Miss Bennet: Christmas At Pemberley @ The Cascades Theatrical Company, Bend

  • FRI-SUNA sequel to Jane Austen’s Pride and Prejudice set two years after the novel ends, MISS BENNET continues the story, only this time with bookish middle-sister Mary as its unlikely heroine. Mary is growing tired of her role as a dutiful middle sister in the face of her siblings’ romantic escapades. When the family gathers for Christmas at Pemberley, an unexpected guest sparks Mary’s hopes for independence, an intellectual match, and possibly even love.


Saturday, Dec. 14

2nd Saturday Reception @ Artists’ Gallery, Sunriver

  • SAT – Join us on Saturday, December 14 from 4-6 pm for our monthly artists’ reception. Enjoy beer, wine, and snacks while engaging in lively conversations with our artists and other guests. Finalize your holiday shopping while you’re at it, we have something for everyone in every price range!

7th Annual Central Oregon Winter Beer Festival

  • SATThe 7th Annual Central Oregon Winter Beer Festival returns to Bend, Oregon on Saturday, December 14th from 2:00-9:00 pm. Hosted by GoodLife Brewing and Bigfoot Beverages, the Central Oregon Winter Beer Festival will bring together over 20 breweries to this outdoor festival that takes place at Century Center parking outside of GoodLife Brewing.

Brunch With Santa @ The Great Hall, Sunriver

  • SATHave 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!

Father Christmas @ The High Desert Museum

  • SATBring a camera and take a photo with Father Christmas. Our beloved 1880s character of holiday past will be waiting for your wish list in the historic ambiance of the Hall of Exploration and Settlement.

Redmond’s Holiday Village in Centennial Park

  • SATFind 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.

Santa Party @ Roundabout books, Bend

  • SATOur first Santa Party! We’re excited Santa and Mrs. Claus have time to stop in and visit the bookstore. Bring your family and come say “Hello!” ~ Holiday-themed stories ~ Children can write letters to Santa and put them in our mailbox ~ Photo opportunities with Santa and Mrs. Claus.

Santa’s Village in Downtown Bend

  • SATSanta is in Downtown Bend every Saturday in December until Christmas. He is located on Wall Street between Starbucks and North Soles.

Sunriver Wine and Cuisine Stroll

  • SATJoin us at Sunriver Resort in the Main Lodge where Carson’s American Kitchen will be hosting the Sunriver Wine and Cuisine Stroll featuring Washington wines. This fun and festive event will feature tastings from Washington wineries as well as creative bites from Sunriver Resort’s executive culinary team (menu below). Live music by local talent KC Flynn, from 12:30 pm – 4:00 pm. Tickets include a commemorative tasting glass, appetizers, and entry to the tasting event.

Ugly Sweater Pub Crawl @ Downtown Bend

  • SATGet Ugly with us and raise money for Downtown Bend! 4-6 pm – Check-in at Bend Brewing Co. & pick up your free drink tickets and swag + Hang out for the pre-party and have a beer! 6 pm – 8 pm – Pub Crawl through Downtown Bend and spend your free drink tickets! Participating locations include Deschutes Brewery, The Astro Lounge, Crater Lake Spirits Tasting Room, The Wine Shop And Beer Tasting Bar Bend, Velvet Bend, Duda’s Billiards Bar, and more!


Sunday, Dec. 15

Bend Pops Orchestra @ the Bend Senior Center

  • SUNMark your calendars! We are playing two FREE concerts in Bend. December 14, 7 PM at Trinity Lutheran, and December 15, 2 PM at the Bend Senior Center. Admission is FREE and home-baked treats and coffee will be served at intermission. See you there!

Breakfast With Santa @ Five Pines Lodge

Central Oregon Mastersingers @ The Tower Theater

  • SUNThe 45-voice chorus, led by Artistic Director Christian Clark, welcomes the 27th Street Brass Quintet and Friends in a holiday concert for choir and brass. The performance includes Daniel Pinkham’s monumental Christmas Cantata, majestic works by Baroque composer Giovanni Gabrieli, and your favorite songs of the season including Hark! The Herald Angels Sing and Joy to the World.

East Meets West – A Musical Meditation @ The Sanctuary, Bend

  • SUNEast Meets West is an innovative collaboration of the wisdom of the East through guided talk meditation and wisdom of the West through healing music. An improvisation performance of hand pans, Native American flutes, silver flute, didgeridoo, drums, and singing.

Travel Oregon Winter Wonderland Event @ Roundabout Books

  • SUNJoin Roundabout Books, Visit Central Oregon, and Travel Oregon as they celebrate the release of the limited-edition storybook “Yeti & Squatch in the Winter Wonderland of Oregon.” The event is free and open to the public. Everyone who attends will receive a free copy of the book and poster (while supplies last).



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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