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  • Beer Dinner with Lucky Woodsman and Terranaut Beer

    Terranaut Beer Taproom 20750 High Desert Lane, STE 106, Bend, OR

    Luckey’s Woodsman x Terranaut Beer Join us for a special Holiday Craft Beer Dinner featuring Terranaut Beer, where bold winter flavors, curated pairings, and chef-crafted dishes come together for an unforgettable evening. This six-course experience blends seasonal ingredients, creative technique, and exceptional brews that highlight the spirit of the season. This isn’t just dinner—it’s a...

  • Jurassic Quest at Deschutes County Fair and Expo Center

    Deschutes County Fair & Expo Center 3800 SW Airport Way, Redmond, OR, United States

    This year’s show features all the excitement of Jurassic Quest with a festive holiday twist. Families can walk among 80+ life-size, animatronic dinosaurs, enjoy interactive exhibits, fossil digs, dino rides, live shows, and get up-close with our baby dinosaurs and expert trainers — all transformed for the season with: Christmas-themed dinosaur backdrops Photos with Santa Elf on the Shelf...

  • Dirksen Derby 18 Snowboard Rally Race

    Mt. Bachelor 13000 SW Century Drive, Bend, OR, United States

    The Dirksen Derby 18 Snowboard Rally Race returns to Mt. Bachelor this December 19-21, 2025! This iconic event invites the international snowboard and sit-ski communities together for an incredibly fun and memorable weekend. This event features 100% hand-crafted parallel banked slalom race courses, which have been built at a different location on the lower mountain...

    Free
  • Dirksen Derby at Mt. Bachelor – CANCELED

    Mt. Bachelor 13000 SW Century Drive, Bend, OR, United States

    The goal of the Dirksen Derby is to bring the Snowboard and Sit-Ski communities together for an incredibly fun and memorable weekend full of fast race times, strong friendships and fond memories while donating money to good causes. This timed event features a hand-crafted parallel banked slalom race course, with two 30-second courses designed for...

  • Double Bubble Bars at Viaggio Wine Merchant

    Viaggio Wine Merchant 210 SW Century Drive, Ste 160, Bend

    Double the fun in December! Our Champagne Bubble Bars are just what you need to make it through the holiday madness.  We’re here for you with two full weekends of gorgeous Champagnes flowing by the flight or by the glass.  Take a break and treat yourself.  European small plates available too!

  • Santa Comes to the Oxford Hotel

    Oxford Hotel 10 NW Minnesota Ave, Bend, Bend, OR, United States

    Santa is making a special stop at the Oxford Hotel and he can’t wait to meet you! Bring the little ones for complimentary crafts, cookie decorating, letters to Santa, and a hot cocoa bar! Indulge in the season’s delights with scrumptious food and beverages available for purchase at ROAM.

  • Somewhere That’s Green’s Magical Markets of Merriment

    Somewhere That's Green 1017 NE 2nd St, Bend

    Come meet Sandra Claus, grab a freshly baked cookie, a butterbeer or hot cocoa, and get into the magical mood of winter! New makers each weekend! Nov 29/30, Dec 6/7, Dec 13/14, Dec 20/21. 10 am-5 pm

  • The Amaterra Wine Club Experience

    Amaterra Kitchen + Social Club 909 NW Bond St, Bend

    Step inside the newly renovated Wine Lounge private event space—usually reserved for members only—for a special evening of live oyster shucking and tasting our vibrant Blanc de Noir. This event is open to everyone, giving you a taste of what it’s like to be part of the Amaterra Wine Club community. Enjoy our special offer...

  • Deck the Walls at Bend Brewing Co.

    Bend Brewing Co 1019 NW Brooks St, Bend

    A 16’ wide x 12’ tall wall ride for a snowboard/ski competition @bendbrewingco. The wall will be plexiglass with round metal coping on top. // The timing is awesome because it will be happening during the @dirksenderby weekend.  // 3D rendering by @eperrett // Wall build by @black_diamond_woodworks

  • Somewhere That’s Green’s Magical Markets of Merriment

    Somewhere That's Green 1017 NE 2nd St, Bend

    Come meet Sandra Claus, grab a freshly baked cookie, a butterbeer or hot cocoa, and get into the magical mood of winter! New makers each weekend! Nov 29/30, Dec 6/7, Dec 13/14, Dec 20/21. 10 am-5 pm