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18 Essential Holiday Events in the Bend Area 2018

  |  Central Oregon, Happenings, Local Happenings, Neighborhood Insight

Believe it or not, we are gearing up for the holiday season and all its glory. Central Oregon is bustling with excitement this time of year, from Santa visits to festive concerts, and parades to holiday shopping bazaars.

Get in the spirit for the season with these upcoming holiday events in Bend and the surrounding area!


Old Fashion Christmas

November 10–11 | Saturday 9 a.m.–5 p.m. + Sunday 10 a.m.–4 p.m.

Deschutes County Fairgrounds, Redmond

Old Fashion Christmas Redmond, OR

Get your holiday shopping done early at Old Fashion Christmas at the Deschutes County Fairgrounds in Redmond. Step into an old-fashioned indoor atmosphere with a myriad of vendors selling gifts, arts, crafts, food, and some antiques. There will also be live entertainment, a candyland maze leading to Santa, a couple of resting stations playing classic holiday movies, and various Christmas decor and activities all around. Admission is $5 and the donation of a canned good, which will be given to Lil Bit Food Pantry. The show is from 9 a.m. to 5 p.m. on Saturday and 10 a.m. to 4 p.m. on Sunday.


The 19th Annual Food & Gift Festival

November 16–18 | Friday + Saturday 10 a.m.–6 p.m. + Sunday 10 a.m.–4 p.m.

Deschutes County Fairgrounds, Redmond

Return to Redmond for another weekend of holiday shopping fun! This festival at the Deschutes County Fair & Expo Center is one of the largest holiday celebrations in the Northwest, attracting thousands of attendees each year. Get your holiday shopping done early as you visit with exhibitors displaying one-of-a-kind gifts, including art, crafts, jewelry, clothing, wood, music, photography, toys, Christmas decor, and more. There will also be a gourmet food area with a range of items, including tea, chocolates, pasta, soups, dips, meats, coffee, jams, shortbread, salsas, oils, vinegars, honey, sauces and more! General admission is $6 for adults (cash only) and free for children 12 and under.


Santa Flies Into SantaLand at the Old Mill District

November 23 | 10:15–11 a.m.

Old Mill District, Bend

Don’t miss the exciting start to the holiday season at the Old Mill District, as Santa flies into SantaLand, where he will be stationed leading up to Christmas. See Santa land in the Les Schwab Amphitheater and chat with him for a few minutes before he heads over to SantaLand, which will be between Desperado and Avalon Salon.


Community Tree Lighting

November 30 | 4 p.m.

Downtown Bend

Community Tree Lighting Downtown Bend, OR

Downtown Bend comes to life at this beloved annual tradition. The community tree lighting at Crow’s Feet Commons will start at 4 p.m. with games, drinks and games for all ages to enjoy. Plus, there will be music, Bob Shaw from NewsChannel 21, and of course — Santa Claus himself! Mark your calendars so you don’t miss the excitement as the large holiday tree is illuminated for the first time this holiday season.


Cascades Theatrical Company Presents “Miracle on 34th Street”

November 30–December 22 | Varying

Cascades Theatre, Bend

See the classic “Miracle on 34th Street” story come to life at the Cascades Theatre all season long. The play follows the story of an old man going by the name of Kris Kringle, who fills in for an intoxicated Santa in the annual Macy’s Thanksgiving Day Parade — and eventually in the department story in midtown Manhattan. When Kringle claims he really is Santa Claus, his case is brought to court to determine his authenticity. Check out the various dates for this performance and get your tickets in advance!


Gingerbread Junction at Sunriver Resort

December 1–January 1 | All Day

Sunriver Resort, Sunriver

This free come-and-go event is a beloved tradition at Sunriver Resort. The 23rd Annual Gingerbread Junction will feature an impressive collection of gingerbread houses in the Abbot Room of the resort’s lodge from December 1 through January 1. Admire the outstanding craftsmanship of structures created with just candy and cookies!


Bend Christmas Parade

December 1 | 12 p.m.

Downtown Bend

Bend Christmas Parade Bend, OR

Photo Courtesy of the Downtown Bend Business Association

The ever-popular Bend Christmas Parade is kicking off the holiday season and the month of December with festive fun for all ages! Debuting a theme of “Sharing Christmas Joy,” the parade winds through downtown Bend, featuring marching bands, fun floats, and of course — an appearance from Santa himself. The parade starts at 12 p.m. and is free to attend.


Santa Claus in Downtown Bend

December 1, 8, 15 + 22 | 12–4 p.m.

Downtown Bend

After he arrives by parade, you can visit with Santa in downtown Bend every Saturday from 12 to 4 p.m. Little ones can sit on his lap and tell him what they’d like for Christmas. In addition to parade day (December 1), Santa will be in town every Saturday at Beach Hut Deli!


Menorah Lighting at the Old Mill District

December 2 | 5–6:30 p.m.

Old Mill District, Bend

Celebrate Chanukah at the Old Mill District on the first night of Chanukah. This annual tradition features music, hot drinks, potato latkes, a jumbo dreidel, and The Great Chanukah Gelt Drop, where you gather chocolate coins as they rain down! Don’t miss this fun celebration on Tuesday, December 2 starting at 5 p.m.


Jim Brickman “A Joyful Christmas” at Tower Theatre

December 3 | 7:30 p.m.

Tower Theatre, Bend

Jim Brickman “A Joyful Christmas” at Tower Theatre Bend, OR

Photo Courtesy of Jim Brickman

Best-selling solo pianist Jim Brickman is coming to the Tower Theatre for a special Christmas performance for one night only! This hit-making songwriter has had two Grammy nominations, two SESAC Songwriter of the Year Awards, and a Canadian Country Music Award. Get in the spirit for the holiday season with this joyful performance featuring a number of Christmas classics. Tickets range from $50–73.


Journey to Bethlehem

December 5, 7, 8 + 9 | Wednesday + Friday 6–9 p.m., Saturday + Sunday 5–9 p.m.

Bend Seventh Day Adventist Church, Bend

Take a journey back to the sights, sounds and smells of the very first Christmas Eve in the bustling town of Bethlehem. This live-action walk-through experience features over 100 actors and live animals in a realistic historic setting. No reservations are needed, and admission is free! Visit the Journey to Bethlehem from 6–9 p.m. on Wednesday and Friday or 5–9 p.m. on Saturday and Sunday. Dress appropriately for this outdoor, walk-through experience!


Holiday Magic at Tower Theatre

December 8–9 | Saturday 3 p.m. + 7 p.m., Sunday 3 p.m.

Tower Theatre, Bend

Holiday Magic returns to Tower Theatre for the 2018 holiday season with three special performances on December 8 and 9. The performance showcases the musical talents of the Cascade Chorale, and the matinee performances will also feature the talented Bend Children’s Choir. The evening performance on Saturday will showcase Bend Camerata, an exceptional chamber ensemble with a diverse classical choral repertoire. Listen to a wide range of holiday music, including traditional carols like “Silent Night” and light-hearted contemporary tunes like “A Charlie Brown Christmas.” Tickets for Holiday Magic range from $15–25.


Central Oregon Winter Beer Festival

December 8 | 2–9 p.m.

GoodLife Brewing, Bend

Central Oregon Winter Beer Festival Bend, OR

GoodLife Brewing Company is hosting the 6th Annual Central Oregon Winter Beer Festival, a showcase of seasonal and specialty beers brewed in celebration of the holiday season. Proceeds from admission will go to the Central Oregon Brewers Guild. Sip on seasonal beers and enjoy delicious eats from local food trucks, which will be parked on site.


Tetherow Holiday Bazaar

December 12 | 4–8 p.m.

Tetherow Event Center, Bend

Tetherow Holiday Bazaar

Graphic Courtesy of Tetherow

Head to the beautiful Tetherow Event Pavilion for an evening of inspired holiday shopping. This event features local artisans and businesses presenting one-of-a-kind products and services just in time for the holidays. Shop for friends and family while you enjoy appetizers and beverages at Tetherow’s 6th Annual Holiday Bazaar. This event is open to the public and admission is completely free!


Holiday Lights Winter Paddle Parade

December 14 | 4 p.m.

Tumalo Creek Kayak & Canoe, Bend

This annual tradition is so quintessential and authentic to the character of Bend. Every year, the area’s most dedicated paddling enthusiasts adorn their canoes and kayaks in holiday garb and paddle around the Deschutes River. This exciting event gets paddlers and onlookers alike in the holiday spirit. Paddlers will meet at Tumalo Creek Kayak & Canoe on Friday, December 14 at 3 p.m. to decorate their kayak or canoe. After a crowd assembles, they will depart from the dock at 4 p.m. and paddle upstream up to the Flag Bridge. On the way back, they will assemble in formation, allowing friends and families to take photos of the decorated boats. Spectators should plan on seeing the decorated boats starting at approximately 4:15 p.m. After the paddle, everyone is welcome to enjoy warm beverages at Tumalo Creek Kayak & Canoe.


Ugly Sweater Pub Crawl in Downtown Bend

December 15 | 5–8 p.m.

Downtown Bend

Ugly Sweater Pub Crawl Bend, OR

Graphic Courtesy of the Downtown Bend Business Association

Don your ugliest sweater and head to downtown Bend for the Ugly Sweater Pub Crawl. Christmas festivities, ugly sweaters and craft beer — what more could you ask for? The crawl will take place from 5–8 p.m. in the downtown area.


Central Oregon Mastersingers Presents Magnificat!

December 15–16 | Saturday 7:30 p.m. + Sunday 2 p.m.

Tower Theatre, Bend

Led by artistic director Christian Clark, the Central Oregon Mastersingers’ annual holiday concert will feature John Rutter’s Magnificat along with a number of favorite carols and songs of the season, including Silent Night, Hark! The Herald Angels Sing, and The First Noel. Don’t miss this inspiring performance — on either Saturday night at 7:30 p.m. or Sunday afternoon at 2 p.m.


A Swingin’ Tower Christmas at Tower Theatre

December 21–23 | Friday 7 p.m., Saturday 3 p.m. + 7 p.m., Sunday 3 p.m.

Tower Theatre, Bend

End the holiday celebrations with a bang at A Swingin’ Tower Christmas at the Tower Theatre. This family-friendly show features songs, stories and dances by Central Oregon’s top performers — all backed by a swingin’ 14-piece band! Don’t miss the show’s several performances in the days leading up to Christmas — including December 21 at 7 p.m., December 22 at 3 p.m. and 7 p.m., or December 23 at 3 p.m. Tickets for A Swingin’ Tower Christmas cost $17 for adults and $12 for children 12 and under.


Happy Holidays!

How are you celebrating the holidays in Central Oregon? Let us know what events you’re looking forward to!

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About the Author

Courtney Itami

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