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  • Purpose Derby

    Commonwealth Pub 30 SW Century Drive, Bend

    Bend’s most spirited Kentucky Derby watch party, including Live and Silent Auctions, Derby Hat Contest, Games and Activities, Food Truck Fare and Signature Cocktails - all to support StirrUp Purpose programs.

    Free

  • Jump for Joy: Toddler Time

    Mountain Air Trampoline Park

    Enjoy Toddler Jump Time at Mountain Air! Tickets at https://www.mountainairbend.com/tickets/ Registration is required via the Mountain Air website. Reservations will be available starting three weeks before the program. To register, visit the Mountain Air website or click the "register" button to the left, scroll down to "Bookings," enter "May 5th," hit "Continue," and then select "Story …

    Free

  • 30th Annual COCC Jungle Run

    Central Oregon Community College 2600 NW College Way, Bend, OR, United States

    The 30th Annual COCC Jungle Run/Walk features a 4-mile or 2-mile trail course with single-track trails, mud bogs, steep climbs, and obstacles. Enjoy a fun, challenging race with prizes, food, and a free t-shirt. Spot a fake snake on the course to win an extra prize (real snakes not included)! FREE FOR ALL COCC STUDENTS. Cost for …

    Free – $15

  • 30th Annual COCC Storm the Stairs

    Central Oregon Community College 2600 NW College Way, Bend, OR, United States

    The 30th Annual COCC Storm the Stairs run is stair-filled run across COCC's scenic hillside Bend campus, including through buildings. Open to all skill-levels, this is a great way to explore campus, win a prize, and get a free T-shirt and food. FREE FOR ALL COCC STUDENTS. Cost for community members is $15 (plus online processing fees), …

    Free – $15

  • Bend Summer Crit Series

    Recurring

    The Horner Cycling Foundation is excited to announce that they will run the Bend Summer Criterium Series again beginning June 24 and ending July 22, 2026.  The 5-week series will take place around High Lakes Elementary School.  NW Sacagawea Lane, NW Meriwether, NW High Lakes Loop and NW John Fremont that surround High Lakes Elementary …

    $25

  • Oregon High Desert Classic Horse Show

    J Bar J Youth Services 62895 Hamby Rd, Bend, OR, United States

    Join us for the largest equestrian Hunter and Jumper show in Central Oregon! Watch world-class riders and their horses navigate jumps in some of the last remaining grass footing rings in the country. This show is the primary annual fundraiser for J Bar J Youth Services, a local nonprofit organization that facilitates positive change for …

    Free