EVENT DATE : May 25, 2:30AM
Riverbend Park

The Happy Girls runs support healthy choices and positive self-image for first-time racers and seasoned runners alike. The all-woman’s race mixes a course along trails and the Deschutes River with paved trails. HappyGirlsRun.com

EVENT DATE : May 25, 6:00PM
Faith, Hope, and Charity Vineyards and Events Center, Terrebonne

Doc Ryan and The Wychus Creek Band play folk, blues, rock, gospel, alternative country. Enjoy fine wines, craft beer, sangria, and hand-crafted food at the family-friendly vineyard. Admission, $5-$10. FaithHopeandCharityEvents.com

EVENT DATE : May 26, 8:00AM
Three Creeks Brewing, Sisters

The Memorial Day race is the largest in Oregon with a course winding through the Peterson Ridge trail system. There are 25 different race categories with a course that features views of the Three Sisters Mountains. SistersStampede.com

EVENT DATE : June 2, 9:00AM
Drake Park

The annual event, held on National Cancer Survivors Day, raises funds for Sara’s Project which provides education, early detection, and support services to ease the challenges of breast cancer for people in Central and Easter Oregon. StCharlesHealthcare.org

EVENT DATE : June 5-9
Sisters Rodeo Grounds

Priding itself with high-quality rodeo stock and high purses, the Sisters Rodeo draws top competitors for events ranging from a buckaroo breakfast to Xtreme Bulls. SistersRodeo.com

EVENT DATE : June 8-9
Sisters Creekside Park

In its 15th year, the event features arts, crafts, food, entertainment and a special fundraiser benefiting the Make-A-Wish Foundation of Oregon. MetalMountain.net

EVENT DATE : June 14-16
Downtown Bend

This three-day celebration in downtown Bend is devoted to celebrating restauranteurs and food lovers from across the region. The event offers food, beer, spirits and music all weekend, plus a conscious-living marketplace, Beer (and Root Beer) Run, Mixology Showcase and a Top Chef competition. BiteofBend.com

EVENT DATE : June 14-16

"Rendezvous with Risk," hosted by OSU-Cascades MFA Writing Program in Bend, includes a keynote lecture, readings, panels, writing workshops, art installations and a Beer & Books event. This year's event celebrates nationally-recognized storytellers and Oregon-based artists who work at the intersection of art-making and risk-taking and is designed for readers, writers and those interested in contemporary literature. OSUCascades.edu  

EVENT DATE : June 16, 11:00AM
Deschutes County Fair and Expo Center

The Bend/Sunrise Lions Club hosts the 49th Annual Father’s Day Demolition Derby. Proceeds benefit the community projects of the Lions Club. BendSunriseLions.org

EVENT DATE : June 20-23
Stevenson Ranch

World-class musicians perform in a family-friendly festival setting with Cascade Mountain views at the 100+ acre Stevenson Ranch. Three stages of music, “Kidlandia,” vendors, yoga, silent disco, a movie under the stars, campground jams and acoustic performances highlight the weekend event. 4PeaksMusic.com  

EVENT DATE : June 21-23
Pine Nursery Park

The Central Oregon Classic Pickleball Tournament is a USAPA-sanctioned event organized by the Bend Pickleball Club. The tournament is open to all ages. Advanced registration is required as is membership in the USAPA. BendPickleballClub.com 

EVENT DATE : June 27, 2:30AM
Les Schwab Amphitheater

Michael Franti returns to Bend for a summer tradition of uplifting rock, reggae and uplifting soulful sounds. Franti performs with Spearhead and Ziggy Marley. BendConcerts.com

EVENT DATE : June 28-30
In and Around Sunriver

The 22nd annual event has something for everyone including the 72.3 BEASTMAN, Olympic & Ultra-Sprint Distance Triathlon/Duathlon/AquaBike, Marathon, Half Marathon, 5K/10K, 28K & 50K Trail Run, Bike Tours and Kids Races. WhyRacingEvents.com