Small-Town Warmth Under Big Winter Skies
A crisp chill is settling in, but downtown is glowing. The scent of juniper and woodsmoke drifts into the evening air. As you walk down 6th Street, you hear the faint sound of clinking of mugs, and the familiar laughter of neighbors running into each other outside local shops.
Winter out here has a way of slowing life down just enough to appreciate it. While the Cascade peaks tower in the distance, Redmond takes on the feel of a quaint holiday scene straight out of a classic storybook. It’s unfussy, welcoming, and built on community traditions that run deep. If you’ve been looking for that genuine holiday feeling, you’ll find it here.
Experience the Glow of the Starlight Parade
There’s something special about claiming a spot on the curb with a thermos of hot cocoa while the daylight fades. When the Starlight Parade starts rolling through downtown, the whole corridor lights up from end to end. You’ll see everything from local fire engines wrapped in bright twinkling bulbs to flatbeds carrying school choirs and vintage tractors sporting wreaths. It’s delightfully homegrown—the kind of parade where the folks on the floats are waving directly to friends they spot in the crowd.
Gather for the Tree Lighting
As the parade wraps up, the crowd naturally drifts toward Centennial Plaza for the annual tree lighting. There’s a quick countdown, a breath of quiet anticipation, and then the big evergreen bursts into a wash of brilliant color. It’s simple, timeless, and totally celebratory. Standing shoulder-to-shoulder in the cool night air while carols ring out across the plaza is usually the exact moment the season officially feels underway.
Stroll the Holiday Village Market
There’s the holiday shopping you do at frenzied malls. Then there’s the kind you do in Redmond at the Holiday Village Market. Here, it feels more like an open-air gathering of friends who happen to make incredible things. Wander among the cozy booths to find handcrafted goods, artisan pantry treats, small-batch preserves, and hand-poured candles. Grab a warm spiced cider, take your time browsing, and talk directly with the makers behind the tables. Suddenly, your holiday gift hunting turns into an easy, relaxed affair.
November 27th and 28th, 2026 10am – 4pm
December 5th and 12th, 2026 10am – 6pm
Located at Centennial Park
Explore the Annual Snowflake Boutique
Fifty years is a long time for any local holiday tradition to stick around, but once you step inside the annual Snowflake Boutique, you can see why it’s been a Redmond staple for so long. Looking through handcrafted quilts, knit hats, rustic holiday decor, and fresh baked treats by people who live here, it’s like you’re part of the community. Generations of local makers have kept this market alive, for an experience that feels less like retail shopping and more like seeing what your neighbors have been pouring their hearts into all year.
November 6th, 2026 1pm – 8pm
November 7th, 2026 9am – 5pm
Located at the Deschutes County Fairgrounds in the Cascade Lakes South Building
Write a Letter to Santa
If you’re exploring downtown with the kids, bring along an envelope or two, and feed into the holiday magic. Redmond sets up a dedicated North Pole mailbox right under the Redmond Arch, ready to accept handwritten wish lists and crayon-drawn masterpieces. Watching little hands slip their letters into the slot is pure nostalgia. Better yet, Santa’s local helpers make sure the magic stays real with thoughtful return notes that keep childhood wonder alive for another year.
Before You Go:
- Layer Up Generously: Central Oregon winter nights drop to freezing quickly once the sun dips behind the mountains, so pack a heavy coat, a warm beanie, and insulated gloves.
- Bring a Sturdy Tote: Between the boutique and the holiday market, you’ll likely pick up fragile handmade goods and baked treats that deserve safekeeping.
- Keep Cash on Hand: While most vendors take cards, a few independent artisans and youth booths move much more quickly with simple cash transactions.
Finding the holiday spirit doesn’t require an over-the-top production. In Redmond, it’s as simple as pulling on a warm jacket, stepping out into the crisp air, and sharing a bright winter evening with a community that knows how to make the season feel like home.
