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  • Silver Oak Wine Dinner at Tetherow

    Tetherow 61240 Skyline Ranch Road, Bend, OR, United States

    An evening of culinary artistry and world-class winemaking awaits at Tetherow. In partnership with Silver Oak, Twomey, and Prince Hill Vineyards, we invite you to gather for an exclusive wine dinner that celebrates the craftsmanship of both chef and vintner.

  • Movies in the Mountains – Hocus Pocus

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

    Experience a classic drive-in movie night at Mt. Bachelor this October. Enjoy a cozy evening with a film under the stars, surrounded by the beautiful Central Oregon landscape. Audio will be broadcast via FM transmission. Tune in from your car radio or bring a portable FM radio if you plan to sit outside your vehicle....

    $25
  • Witches and Wine: Tarot Card Painting Workshop

    Two Suns Art Studio and Makerspace 70 SW Century Drive #190, Bend, United States

    Step into the magic of October with an evening of creativity, intuition, and a touch of the mystical. Join artist Michelle Schultz for Witches & Wine, a painting experience where you’ll design and paint your very own tarot card. Whether you’re inspired by classic tarot imagery or wish to channel your personal symbolism, Michelle will...

    $65
  • Latin Dance Party at Wildwood Bar and Grill

    WildWood Bar and Grill 550 SW Industrial Way #120, Bend, United States

    Come join us for a sizzling hot Latin Dance Party at Wildwood! Get ready to move your hips to the rhythm of the best Latin beats by DJ SOLO. Whether you’re a seasoned dancer or just looking to have some fun, this event is perfect for everyone. So grab your friends and get ready to...

  • Happy Girls Run 2026

    Riverbend Park 799 SW Columbia St, Bend

    Grab your bestie and get ready to run happy! The Happy Girls Bend Run is back—inviting women of all fitness levels to celebrate strength, sisterhood, and the joy of movement along the scenic trails and pathways of Central Oregon. Whether you're tackling your first 5K or chasing a new PR in the half marathon, this race...

  • Trunk or Treat at Craft Kitchen and Brewery

    Craft Kitchen & Brewery 62988 Layton Ave Ste 103, Bend, OR, United States

    Get your costumes ready and gather the family for a day of Halloween excitement! Join us for Trunk or Treat, where creativity and spooky fun come together. Date: Saturday, October 25thTime: 12pm-3pm What to Expect: Decked-Out Cars with Creative Trunk DisplaysCandy Galore! Fun for All Ages! Whether you’re dressing up as witches, superheroes, or spooky monsters,...

  • Jackstraw Grand Opening

    Jackstraw Bend 310 Industrial Way, Bend, United States

    Grand Opening on Saturday, October 25th! Tour Bend’s newest apartment community and discover Lava Pass, a new living street for community events. Plus: live music, free pumpkins, family fun, and a hidden speakeasy! Lava Pass + Jackstraw Saturday, October 25 | 12–4PM | Free + open to all

  • Bubbles and Books Night at Dudley’s Bookshop Cafe

    Dudley’s Bookshop Cafe 135 Northwest Minnesota Avenue, Bend, OR, United States

    Join us on October 25th for Books & Bubbles; an evening made for those who love good wine, good stories, and even better company. With a partnership between Dudley’s Bookshop Café and The Good Drop Wine Shoppe, we’ll explore the world of 4 sparkling wines and literary pairings, from crisp and bright, to bold and...

  • Warren Miller’s Sno-Ciety at Tower Theatre

    Tower Theatre 835 NW Wall St, Bend, OR, United States

    Bring on winter with Warren Miller! Join a stacked lineup of Olympians, urban riders, and local legends to carve turns and celebrate our community. From big lines and race gates to urban ski hills and unexpected destinations, Warren Miller’s SNO-CIETY hits theaters nationwide this fall, so snag your tickets at warrenmiller.com. Tickets: Outside+ member presale* starts...

  • Witches and Werewolves Halloween Costume Party at The Cross-Eyed Cricket

    Cross-Eyed Cricket 20565 Northeast Brinson Boulevard, Bend, United States

    Grab your hat and howl at the moon — it’s time for the Witches & Werewolves Bash! Saturday, Oct. 25th at The Cross-Eyed Cricket Dress as a witch, werewolf, or any wild creature and join the fun! FREE Beginner Line Dance Lessons | 8–9PM Dances: “The Witch” & “The Wolf” Costume Party & Open Dance...