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Central Oregon’s True Holiday Magic Comes from Gathering

What comes to mind when you close your eyes and remember your first December in Central Oregon? We’ve all got that one memory—warm enough to melt the frostiest rime and so full of holiday magic it still lifts your spirits today. It’s likely it wasn’t because of tinsel, presents or even a visit from Santa and his reindeer (okay, maybe Santa gets some credit). True holiday magic comes from gathering. In this darkest month of the year, real-life connections light us up. Gathering elevates us, grounds us, and fills us with joy. It reminds us that we belong here. [Photo above by Arian Stevens]

Gather to Nurture Body and Soul

The region’s culture and landscape make it a natural place to congregate. This is true even in this season of short days and colder weather. Bendites know to shrug off the temperatures. They bundle up rather than isolate indoors. We organize Friendsgiving potlucks with new acquaintances who become chosen clans. We invite a new neighbor on a trek into the snowy woods to find the perfect fir. This tradition will connect them to this place forever. We meet long-time friends on the ski trails. We stop at the warming hut’s fire to laugh and reminisce.

These are more than fleeting feel-good moments. The simple act of coming together benefits both physical and mental health. This is according to Kelli Singer, a functional medicine health coach in Bend. “Spending time with others releases oxytocin, often called the love hormone, and dopamine,” she said. Dopamine is the brain-boosting hormone. “Human connection is calming. It lowers stress and inflammation.”

No matter how people choose to celebrate holidays, gathering is at the core of most traditions and rituals. Meeting around holiday meals is especially powerful, according to Singer.

“Food is the bond all people use to celebrate,” she said. “Sharing meals instills a sense that we belong to something bigger than ourselves alone.”

Julie Duke Santa
Julia Duke’s Photos with Santa event at Wintercreek Nursery, Bend

Gather to Embrace Community

Long-time locals and new transplants agree the Central Oregon community is vibrant and valuable. Fully engaging in life here means taking part in local events. It means expanding our social circle. It also means giving back by sharing our time and talents.

Joining Bend’s holiday celebrations is easy. The hard part is fitting all the cheer into a busy calendar. Find a tree-lighting ceremony in cities across Central Oregon. This includes the impressive Grand Illumination at Sunriver Resort on November 22 to kick off the season. See Santa, high school marching bands, and local business floats. They will all be in the Bend Christmas Parade on December 6. This is a tradition for more than 40 years. String twinkling lights on a kayak and paddle the Deschutes River during the Holiday Lights Paddle Parade on December 12.

Creating community can be as simple as connecting with neighbors. Giving back through volunteering helps make the holidays more meaningful. Local organizations depend on volunteer help to accomplish their missions.

“The energy and generosity of our volunteers make it possible for people to share a meal in a friendly, welcoming place,” said Clara Patt. She is the volunteer director at the Family Kitchen in Bend.

Family Kitchen serves more than 12,000 free meals each month in Central Oregon. They rely on volunteers for cooking and serving. “Their work bridges social and class divides. I’m constantly awed by the people who give so much,” Patt said. They ensure all their neighbors can have a proper meal every day. In return, volunteers gain the camaraderie of a team. They also get the satisfaction of making a difference in another person’s life.

Virginia Meissner shelter
Virginia Meissner shelter | Photo by Whitney Whitehouse

Gather to Appreciate Each Moment

Being present is a thread of appreciation that runs through gatherings of all kinds. It’s a mindset that takes intention. It begins before the holiday whirlwind ramps up. Engaging with the people around us helps us to fully enjoy each experience.

Singer suggests strategies for staying centered, calm, and focused. These include yoga, meditation, and breathwork.

“By practicing grounding ahead of the holidays, you can become more resilient to stress,” Singer said. In the season of jam-packed calendars and to-do lists that rival Santa’s, gathering can mean simplifying. “And not every gathering is easy,” she added. “Some are very challenging. In difficult moments, step away to breathe. Check in with your body. Engage your senses to calm down.”

The more a person practices self-care, the easier it becomes to return to your center. Singer suggests shrinking your to-do list. Slow your pace. Shift the focus to what brings the most joy.

Taking the time for self-care helps us to be present for magical moments. These moments remind us why we’re here. Collecting up those moments may be the best gift we could ever give ourselves.

See our event calendar here for chances to get involved in community, no matter what time of year. | Where to Find the Best Holiday Markets Around Bend

The Art of Brown W. Cannon III and Painter K.C. Cannon

Double Vision: Siblings Blend Multiple Mediums

In downtown Bend, the walls of the Hot Box Betty boutique display a vibrant collection of art. These striking pieces come from “Golden,” a decade-long collaborative project. It features the distinct mediums of photographer Brown W. Cannon III and painter K.C. Cannon, who are siblings. Black-and-white photographs of horses and crashing waves become surreal. This happens with layers of oil paint, pennies, and flecks of gold leaf.

“Starlit”
“Starlit”

Roots of Creativity

The siblings were born into a life steeped in art. Brown studied at the ArtCenter College of Design. He spent decades traveling for publications like National Geographic Adventure. Influenced by his Colorado and Hawaiian family ties, he often focuses on horses and surf culture. His meticulously composed images reflect his perfectionism.

K.C.‘s vibrant, textured work contrasts with her brother’s photography. She trained as a dancer but shifted to painting due to injuries. K.C. refined her skills at the School of Visual Arts and the Rhode Island School of Design. Now based in Colorado, her intuitive work emphasizes symbolism and devotion. She shares that her vision is to her kuleana pono—the sacred responsibility to living in integrity.

The series called “Golden” began in 2012 and has since become the thread that pulls the siblings back together across distance and time. They work in flurries when timing is right. The first piece, “Lucky Penny,” came to fruition when K.C. was particularly struck by one of Brown’s images of a horse and rider printed on metallic gold paper. She tentatively asked if she could paint on top of it and the end result made it evident that this collaboration would be something special.

“Initially I wondered how our uniquely different personalities would match up,” said K.C. “But as it turns out, our differences are what allows each piece to stand out.”

“Beyond the Veil”
“Beyond the Veil”

The two art mediums are as distinct as the artists themselves, but that is what makes their collaborative pieces so striking. Brown approaches his images with a scientific exactness.

“I am a perfectionist of sorts,” he said. “When I hand a print over to my sister, my belief is that it is ready to be framed; however, she sees a canvas that has only just begun.”

K.C.’s job then is not to finish what her brother started but to expand it. She meets his precision with a deep intuition, revealing a new dimension to the images that isn’t immediately visible.

Their creations are striking, but for the siblings it’s less about the finished product. For them, the spark and beauty of their work lives not simply in the final image but in the act of creating art. The practice continues to draw them back to one another across years and miles. As K.C. puts it, “Creating with him is truly golden.” 

Learn more about K.C. Cannon, or Golden, the collaboration of alchemy between sister and brother.

Best Holiday Markets in Central Oregon

The holiday season is upon us, and with it comes the perfect excuse to indulge in some local shopping. Central Oregon’s holiday markets are the place to get into the spirit, offering everything from one-of-a-kind gifts to warm, seasonal drinks, vibes and community cheer. Whether you’re hunting for that one-of-a-kind find or just soaking up the festive atmosphere, these markets are the ideal place to make your season even brighter. Ready to shop? Let’s go!

UPP Liquids Holiday Makers Market

November 15th | UPP Liquids

UPP Liquids Holiday Makers Market is your destination for artisan beverages and craft cocktail essentials this holiday season. From small-batch bitters and house-made syrups to unique spirits and premium mixers, you’ll discover all the locally crafted libations your bar cart needs. The festive atmosphere, expert tastings, and seasonal sips make it the perfect spot for an afternoon of spirited holiday shopping from local makers and artists.

Sunriver Saturday Holiday Market

November 29st | SHARC

For those seeking gifts with a little extra heart, the Second Annual Sunriver Saturday Holiday Market at SHARC is the place to be. This cherished community gathering brings together local artisans and creators showcasing their handcrafted treasures—from unique home décor to one-of-a-kind keepsakes. It’s perfect for anyone who wants to find meaningful gifts while supporting the talented makers in our own backyard.

Bend Moonlight Market

November 29th | Midtown Ballroom

If you like your markets with a side of eclectic fun, Bend Moonlight Market is the place to head to. With free entry and a lively mix of local vendors, food, live music, and even flash tattoos, this is the place to pick up gifts that are as unique as you are. Perfect for a festive night out with friends—and don’t forget to stop by the food carts for a bite while you’re at it.

Downtown Thump Holiday Makers Market

Dec. 5 | Downtown Thump

Thump Downtown Holiday Market brings together the best of local craftsmanship for your holiday shopping needs. Browse curated collections of handmade ceramics, vintage goods, candles, stained glass and more—all created by independent artisans.

Holiday Market at Bend Brewing Co.

Dec. 5 | Bend Brewing Co.

Looking for a holiday market where you can check out local artists’ wares with a fan favorite beer in hand? Bend Brewing Co. Holiday Market has you covered.

Sunriver Brewing Co. Annual Holiday Makers Market

Dec. 6 | Sunriver Brewing Co. 

Sunriver Brewing Craft beer meets holiday shopping at Sunriver Brewing’s Annual Holiday Makers Market. Browse local artisans, snag unique gifts, and enjoy a pint or two in a festive atmosphere. It’s the perfect way to support local makers while crossing names off your holiday list.

Somewhere That’s Green Magical Markets of Merriment

Nov 29/30, Dec 6/7, Dec 13/14, Dec 20/21 | Somewhere That’s Green

If you’ve ever wanted to shop in a winter wonderland, Somewhere That’s Green is making it happen. With dates spread throughout the season, these Magical Markets of Merriment offer cookies, hot cocoa, butterbeer and a chance to meet Santa. It’s the perfect place to find something special, all while soaking in the pure holiday magic that this market serves up in spades.

Holiday market somewhere that's green

Faith Hope & Charity Vineyards Holiday Market

November 29th & November 30th | Faith Hope & Charity Vineyards  

Set against the stunning Three Sisters, Faith, Hope & Charity Vineyards is offering the ultimate holiday market experience. Enjoy award-winning wine, wood-fired pizzas and locally-made gifts all under one roof. With a heated tent and festive vibes, you’ll find yourself lingering longer than you planned.

The Barn in Sisters Holiday Market

November 30th & December 6th | The Barn in Sisters

Discover one-of-a-kind treasures at The Barn in Sisters Holiday Market, where local artisans showcase their finest holiday creations. The rustic charm and festive ambiance set the stage for relaxed browsing through handwoven textiles, artisan home décor, gourmet treats, and unique gifts. With live artisan demonstrations and seasonal touches throughout, it’s an inviting escape for finding those special curated pieces.

santa and kid at shillings
Holiday Market at Schillings Garden Market

Schilling’s Garden Market Holiday Makers Market

December 6th & 7th | Schilling’s Garden Market 

Get ready for a holiday market full of everything—from handmade wreaths to artisanal food and live music. Schilling’s Holiday Makers Market is the place to be for festive fun, with a portion of parking proceeds benefiting the Family Access Network. Plus, who doesn’t love a visit from Santa?

Photo by Julia Duke

Bevel Craft Brewing Holiday Market

December 6th & 7th | Bevel Craft Brewing

Bevel Craft Brewing transforms into a festive marketplace where craft beer meets local artistry at the Bevel Holiday Market. Sip seasonal brews while browsing handmade treasures from regional makers—custom leather goods, artisan foods, handcrafted décor, and unique gifts. The lively brewery vibe and great beer make for an unforgettable holiday shopping experience.

The Workhouse: 14th Annual Craft-O!

December 13th & 14th | The Workhouse

Craft-O! is Bend’s go-to holiday market for all things handmade. From ceramics and jewelry to candles and soaps, you’ll find all the locally crafted goods your heart desires. The relaxed vibe, live music and warm drinks make it the perfect spot for a day of stress-free holiday shopping.

holiday market at Craft-O
Craft-O | Photo by Arian Stevens

Want more holiday cheer? Check out all of the holiday happenings you can find throughout Central Oregon this year.

Giveaway from Lazy Z Ranch and Luckey’s Woodsman

THIS CONTEST HAS ENDED. Please sign up for our newsletter and keep following @bendmagazine so you will be the first to know about our next three giveaways to come.

Enter to win $25 from Lazy Z Ranch AND $25 to Luckey’s Woodsman’s Food Truck in Sisters! Contest runs through Sunday, November 23, 2025 at 11:59 PST. One winner will be chosen to win both gift cards and notified via email on Monday, November 24, 2025. Please include a real email address, as it’s the only way to be notified of how to receive your prize. Please see the full rules here.

Luckey's Woodsman Jackson Higdon
Luckey’s Woodsman | Photo by Arian Stevens
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