A Local Guide to Winter Happenings in Central Oregon

Winter at Caldera Springs is about more than snow-covered trails and cozy evenings at home—it’s a season that invites you to venture outside, connect, and experience the vibrant culture of Central Oregon. From intimate lakeside gatherings to wellness-focused outings and beloved regional festivals, the winter calendar is filled with moments worth savoring.

 

Bingo at Lake House

Thursday, 4:00-5:00pm

Whether you’re playing for prizes, savoring happy hour bites, or simply enjoying the cozy atmosphere, Bingo is the perfect way to spend an afternoon at Lake House.

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Live Music at Lake House

Friday Nights, 5:15-7:15pm

Ease into the weekend with live music at the Lake House, where local musicians set the tone for relaxed winter evenings at Caldera Springs. Gather with friends, settle in by the fire, and let the music carry you from day to night as the sun dips behind the pines. It’s an effortless way to reconnect with neighbors and celebrate the close of another beautiful week.

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Snowshoe Forest Bathing at Sunriver Resort

Select Dates Throughout the Season

This guided snowshoe experience blends gentle movement with mindfulness, inviting you to slow down and fully take in the winter landscape. Led by a wellness guide, the journey winds along the Deschutes River or through quiet ponderosa pine forests, with moments to stretch and reflect amid the stillness of snow-covered ground. Designed for all skill levels, this immersive outing offers a restorative way to experience winter.

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Full Moon & Yoga Sound Healing at Sunriver Resort

January 31 & February 28, 7-8pm

Mark the full moon with an evening of intention and calm at Sunriver Resort’s indoor movement studio. This gentle yoga class pairs slow, grounding movement with sound healing designed to restore balance and release tension. Warm, welcoming, and accessible to all levels, the experience includes herbal tea and infused water before and after class—creating space to unwind, reset, and move through winter with clarity and ease.

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2026 Canine Keg Pull at The Village at Sunriver

February 7, 11am-3pm

One of Sunriver’s most beloved winter traditions returns with a day dedicated to dogs, community, and a great cause. The Canine Keg Pull brings together locals and visitors alike for lighthearted competition, festive energy, and plenty of tail-wagging fun. With dog-friendly vendors, a photo bus for keepsake snapshots, and proceeds benefiting the Ronald McDonald House, this event is as heartwarming as it is entertaining—whether you’re racing or cheering from the sidelines.

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Superbowl at Forest House

February 8, 3:00pm

Game day gets a Central Oregon twist at Forest House, where the Super Bowl is shown on the big screen alongside food, drinks, and casual entertainment. Between plays, enjoy bowling, games, and a lively atmosphere fueled by Piney’s game-day menu. Signature cocktails—including the ever-popular Chicken & Waffle Bloody Mary—round out an experience that’s equal parts spirited and social.

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Sip N’ S’mores at Forest House

February 15, 3-4pm

This elevated take on a campfire classic transforms s’mores into a savory, interactive tasting experience. Roast a curated selection of cheeses over the fire and pair them with crackers, candied bacon, fig jam, and other flavorful accompaniments. Designed for sharing and lingering, Sip N’ S’mores is a cozy winter gathering that feels both playful and indulgent, perfect for an afternoon spent with friends or family.

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Sunriver Stables Sleigh Rides

Select Dates Through February 15, 10:45am Start

Few winter experiences feel as timeless as a horse-drawn sleigh ride through snow-covered meadows. Departing from Sunriver Stables, these scenic rides offer sweeping views of the surrounding landscape and a peaceful way to take in the season. Ideal for families, couples, or anyone looking to embrace a classic winter tradition, each sleigh ride provides an intimate, memorable way to experience Central Oregon in winter.

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Bend WinterFest

February 13-15

Bend WinterFest brings big energy to the heart of the Old Mill District with three days of music, entertainment, and winter celebration. The weekend kicks off with dance-floor-ready performances, continues with nostalgic throwbacks and high-energy tribute acts, and culminates in crowd-pleasing live shows that draw visitors from across the region. Equal parts festival and winter party, WinterFest is a must-see highlight of the season.

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Subaru WinterFest at Mt. Bachelor

March 29, 8am-5pm

Closing out winter on a high note, Subaru WinterFest blends mountain culture, live music, and outdoor lifestyle into a full day of free festivities. With concerts, giveaways, adventure gear demos, snacks, and activities for dogs, the event captures everything Central Oregon loves about winter. Live performances from Shakey Graves and Emily Nenni—hosted at Deschutes Brewery—make this a perfect spring-forward celebration of snow, sound, and community.

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Benefits of owning and staying at Caldera Springs include convenient access to nearby Sunriver Resort and its amenities, opening the door to a rich lineup of seasonal events just minutes from home. Whether you’re in the mood for live music, outdoor adventure, or something a little indulgent, these winter happenings in Caldera Springs, Sunriver, and Bend offer the perfect excuse to embrace the season.