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Oregon's Best Holiday Experiences

Oregon’s Best Holiday Experiences

From coastal lights to mountain sleigh rides, make the most of the season with Oregon’s best holiday celebrations and cozy escapes

written by Cathy Carroll

Oregonians’ winter holiday celebrations are as diverse as its landscape, with each region offering new and time-honored traditions. It’s the perfect chance to sample a bit of both. Dive into a speed-dating comedy show, perfect for a season that often calls for a romantic partner. Let horse-drawn sleigh rides carry you over rivers and through snowy woods. Bask in the glow of thousands of colorful lights illuminating botanical gardens perched above the sea. Immerse yourself in the fun of floating parade-goers paddling upstream and city-street caroling competitions that challenge you to utter a “humbug.” It’s all here, with inviting retreats offering getaways that impart true and new tastes of local culture and spirit.

A holiday family sleigh ride on the edge of the Deschutes National Forest at Sunriver Resort.
Sunriver Resort

Portland

Fun & Flirty: A Comedy Dating Show

DEC. 12, 7 p.m.

Forget mistletoe. For a love match—and laughs—just in time for the holidays, hook up with Fun & Flirty, the new, homegrown comedy/dating show. Comedian hosts Zahnae Aquino and Jesse Warren explore the essence of dating—Pacific Northwest style. The duo pitches some hot, sexy singles to the audience for live, comedic speed dating. This local brand of humor and romance is perfect for the single, dating, divorced, widowed and married, too. It hits the stage at the Tomorrow Theater at Portland Art Museum’s Center for an Untold Tomorrow. www.tomorrowtheater.org/movies/ pdx-speed-dating-presented-by-funflirty-productions

A night out at Fun & Flirty: A Comedy Dating Show at the Tomorrow Theater.
Fun & Flirty

Pee-wee’s Playhouse Holiday Special

Destined to become a celebrated holiday tradition in its second year, the screening of Christmas at Pee-wee’s Playhouse, with cameos from all the late-’80s’ icons, from Cher and Oprah to Portland’s own k.d. Lang, returns to the Tomorrow Theater at Portland Art Museum’s Center for an Untold Tomorrow. A life-size Conky robot draws pictures by hand/metallic claw for guests young and old—more than 500 last year—all sporting red bow ties. Watch for the date to be posted in November. www.portlandartmuseum.org/pam-cut

A viewing of Pee-wee’s Playhouse holiday special at the Tomorrow Theater.
PAM CUT

Oregon Symphony’s Gospel Christmas

DEC. 14, 7:30 p.m.

DEC. 15, 4 p.m.

This twenty-five-year tradition brings together the region’s premier gospel singers and the Oregon Symphony to offer the energizing, joyful and uplifting power of gospel music at the Arlene Schnitzer Concert Hall. www.orsymphony.org/concertstickets/2425/gospel-christmascelebrating-25-years

The Hip Hop Nutcracker

NOV. 14, 7:30 p.m.

Hip hop’s not just for the Olympics this year. This remixed, reimagined version of the holiday classic is a contemporary dance spectacle mash-up of hip hop dance and Tchaikovsky’s timeless music. In The Hip Hop Nutcracker, just like the original, a girl and the Nutcracker Prince go on a dream adventure battling a gang of mice, visiting the land of sweets and learning the lessons of the holiday season. Digital graffiti and visuals transform the landscape of E.T.A. Hoffmann’s beloved story from nineteenth-century Germany to the vibrant, diverse sights and sounds of today’s New York City. The show is directed and choreographed by Tony and Olivier Award-nominated Jennifer Weber, with Kurtis Blow, one of hip hop’s founding fathers, opening the show with a short set at Keller Auditorium. www.portland5.com/keller-auditorium/ events/hip-hop-nutcracker

The Hip Hop Nutcracker will hit the stage at Portland’s Keller Auditorium.
Timothy Norris

Thomas Lauderdale of Pink Martini Live at Portland’s Tree Lighting

NOV. 29, 5:30-6:45 p.m.

The day after Thanksgiving, sing along with Portland’s own Thomas Lauderdale from Pink Martini, local musicians and chorale singers as Santa Claus flips the switch to light up the city’s 75-foot Douglas fir. www.thesquarepdx.org/events

Portland Holiday Brew Fest

DEC. 6, 5:30-9 p.m.

DEC. 7, 12-9 p.m.

DEC. 8, 12-5 p.m.

Quaff from among more than twenty-five holiday and winter beers and ciders from around the Northwest while staying toasty under heated tents. www.pdxholidaybrewfest.com

The Great Figgy Pudding Caroling Competition

DEC. 13, 6-7:30 p.m.

Carolers sing around a ten-block radius of Pioneer Courthouse Square, and the top three groups engage in a “carol-off” at the square. Crowd applause determines the grand prize winner of $1,000. www.thesquarepdx.org/events

33rd Annual Tuba Christmas Concert

DEC. 21, 1:30-3 p.m.

More than 200 tubas play in unison at this longtime, big brass tradition. www.thesquarepdx.org/events

Retreat: The Ritz Carlton

Stroll from the Ritz to the Schnitz and to Pioneer Courthouse Square festivities, shops and more shows from a luxurious holiday haven. Take in the city skyline twinkling with lights from a spacious room in the thirty-five-story property. Savor holiday cheer and Northwest-inspired cuisine at the twentieth-floor signature restaurant, Bellpine. Wrap up the year by rejuvenating at the spa. www.ritzcarlton.com/portland

Central Oregon

Fall River Forest Bathing

NOV. 16, 3 p.m.

DEC. 14, 3 p.m.

Take a cue from the forest about slowing down and resting around the holidays. Bend-based R’oming Yoga’s Missie Wikler, a former field biologist and forest therapy guide certified by the Association of Nature and Forest Therapy, guides you in cultivating deep relaxation and releasing stress. Much more than a walk in the woods, the experience begins with a forest immersion meditation to open you to an intentional connection to the land and a new way to experience nature through a guided sensory practice. www.romingyogabend.com/forest-bathing

Mt. Bachelor’s Christmas Eve Santa

DEC. 24, 10 a.m.-2 p.m.

Old St. Nick stays young by cruising the slopes, passing out candy and taking selfies with fans—a Christmas Eve tradition. www.mtbachelor.com

Sunriver Traditions

NOV. 23-JAN. 1

Sunriver Resort’s 3,300 acres are the idyllic backdrop for horse-drawn sleigh rides through a snowy meadow, sipping hot cocoa by the fire, building a gingerbread house and enjoying a festive feast. It kicks off with the Grand Illumination—a tree lighting and fireworks show with Santa, pony rides, live music, train rides, telescope viewings, hot cocoa, huggable characters, food vendors, dining at the lodge and gift-finding at the Merchant Trader shop. www.sunriverresort.com/traditions

Holiday Lights Paddle Parade

DEC. 13, 4 p.m.

Paddlers clad in holiday garb parade up the Deschutes River through Bend’s Old Mill District in canoes, kayaks, paddleboards—whatever floats—decorated with colorful lights in a thoroughly Bend celebration. Gather along the banks and footbridges as stars appear overhead, the illuminated crafts reflect on the water and the sense of community, creativity and love for the outdoors builds. www.oldmilldistrict.com/event/ holiday_lights_paddle_parade

Paddlers take part in the Holiday Lights Paddle Parade on the Deschutes River in Bend.
Gwen Shoemaker/Old Mill District

Black Butte Ranch

Since 1970, Black Butte Ranch resort’s 1,800 acres is a retreat for wholesome holiday fun, including its Turkey Trot, tree lighting ceremony, breakfast with Santa, sleigh rides and skiing at nearby Hoodoo Ski Area. Sipping cocoa by the fire and morning alpenglow with views of the Three Sisters, Mount Washington, Black Butte, Broken Top, Three Fingered Jack and Mount Jefferson set the stage for mountain holiday magic. www.blackbutteranch.com

Hood River

Polar Express Train Ride

LATE NOVEMBER THROUGH EARLY JANUARY

As soon as the conductor calls, “All aboard!” and the train chugs from the station, the spirit of Christmas permeates the air. Magically, Santa boards at the North Pole within minutes, and while everyone nibbles cookies and sips hot cocoa, they get to tell him what they want to find under their tree. www.mthoodrr.com/train-rides/ polar-express-christmas-train

Hood River Holidays

DEC. 6

Soak up small-town atmosphere, shop small and stay in boutique charm. Make the fully decorated Historic Hood River Hotel your downtown winter base camp for the Holiday Vintage Bazaar or a Santa meet-and-greet with hot chocolate and peppermint schnapps for the parents. Or stay high above the Columbia River at the Columbia Gorge Hotel and walk the gardens, filled with colorful lights. www.visithoodriver.com/events

Holiday decorations in Hood River.
Visit Hood River

Oregon Coast

Heceta Lighthouse B&B + Victorian Christmas Open House

DEC. 14, 15, 21, 22, 4-7 p.m.

The open house, in its twenty-seventh year, transports you to 1894, the year of the first Christmas at the beautifully decorated Keeper’s House. Local musicians, from jazz and string quartets to folk and choral ensembles, generously volunteer performances. Keep your holiday purchases local at the Heceta Lighthouse Gift Shop, and then don a headlamp and jacket for a stroll up to the lighthouse. Follow the Fresnel light, still shining from 205 feet above the Pacific, casting its beams 21 miles out to sea. www.hecetalighthouse.com/ events#christmas

Holiday lights at Heceta Lighthouse B&B.
Heceta Lighthouse B&B

Holiday Lights at Shore Acres State Park

NOV. 28-DEC. 31, 4:30-9 p.m. (including Thanksgiving, Christmas Eve, Christmas Day and New Year’s Eve)

Stroll through an illuminated, 7-acre botanical garden and Japanese lily pond on the rugged cliffs overlooking the Pacific. Since 1987, this celebration has evolved into a spectacle of more than 325,000 holiday lights (nearly all of them LED), twenty-six Christmas trees, illuminated sculptures—including some that are animated—and landscape lights focused on the trees that encircle the garden. This tradition is the result of the efforts of the Friends of Shore Acres and 1,500 volunteers and support from local businesses, state park personnel and the community. www.oregonsadventurecoast.com/event/ annual-holiday-lights-at-shore-acres

Willamette Valley

Eugene Concert Choir Presents Handel’s Messiah

DEC. 15, 2:30 p.m.

Most audiences have only heard the Christmas portion and the “Hallelujah Chorus,” but this is a rare opportunity to hear the excitement of the entire beloved masterwork. The story continues through life, suffering, triumph and redemption—in distinct, dramatic scenes. In Handel’s lifetime, Messiah was so popular that he created numerous versions of the arias and choruses to achieve the finest performances from the artists who sang in his concerts. Today, with so many variations to choose from, every performance of Messiah is a unique experience shaped by the selections of the conductor. www.eugeneconcertchoir.org/ 2024-2025-season/handels-messiah

Eugene Ballet’s The Nutcracker

DEC. 19-22 AND 24, varied matinees and evenings

Orchestra Next performs live to accompany this ballet replete with the sugar plum fairy and en pointe, twirling snowflakes—an annual tradition at Hult Center. www.hultcenter.org/events/ ebc-the-nutcracker-24

Retreat: The Campbell House Inn

Make your Victorian holiday atmosphere complete by getting cozy at this luxurious bed-and-breakfast that dates back to 1892. Take in the wintery acre of landscaped grounds in Eugene’s historic district, old world charm and first-class amenities. Wake to freshly baked scones, and take a short saunter to all the holiday happenings downtown at a range of venues including the Hult Center, Fifth Street Public Market and top-notch restaurants. www.campbellhouse.com

Eugene’s Fifth Street Public Market in holiday dress.
Melanie Griffin/Eugene, Cascades & Coast

Wine Country

Friendsgiving 2024

NOV. 30, 11 a.m.-3 p.m.

This new (second annual) tradition in McMinnville comes from a close-knit group of friends who are also behind twelve dynamic wineries. United by friendship and collaboration, they’ve created a spirited tasting event, pairing exciting new Oregon wines with holidayinspired dishes by chef Brett Uniss of Humble Spirit in McMinnville. It’s a chance to experience some of Oregon’s finest up-and-coming wineries in one place. Approachment, Arabilis, CHO, Corollary, de la boue, Dolores, Liska, Lonesome Rock, Lundeen, Sealionne, Suzor and Vincent will pour their best selections, showcasing a vibrant slice of Oregon’s wine scene.

In the true valley spirit, Friendsgiving gives back, with part of sales benefitting the Yamhill Community Action Partnership, which works to improve the lives of local, low-income residents through housing stabilization, energy services, a regional food bank and youth services. www.corollarywines.com/events/2024/ friendsgiving

People of McMinnville come together for Friendsgiving.
Josh Chang/Foundry 503

Willamette Valley Wine Celebrations

Be it red, white or bubbles, a bottle of something festive and fabulous food pairings are the way to celebrate the year’s end, family and friends. Scores of seasonal events are happening throughout Willamette Valley wine country. www.willamettewines.com

Retreat: The Setting Inn

Newberg, Dundee, Ribbon Ridge and Chehalem Mountain AVAs surround the inn’s Oregon-meets-Europe guest rooms. Unwind at the end of the day in the charmingly renovated barn to exchange gifts next to the fireplace, or in the courtyard with s’mores around the warming fire pits. www.thesettinginn.com/willamette

The Setting Inn in the heart of wine country in Newberg.
The Setting Inn

Eastern Oregon

“Little Works” Art Exhibition and Fundraiser

NOV. 22-DEC. 19

In Joseph, the Josephy Center for Arts & Culture’s “Little Works” Exhibition of small works of art priced under $200 offers a platform for artists to display their talents and raises funds for programs nurturing young artistic talent. Peruse the works to find creative Christmas gifts that give back to others. The exhibition’s opening reception is November 29, from noon to 4 p.m., and coincides with the Stocking Stuffer Black Friday Art Supply Sale. www.josephy.org/event/little-works-2024

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