Oregon Gin Festival
Type: Food and Drink Festival
Location: Oregon Spirit Distillers, Bend, OR
Month: June
Description: Celebration of Oregon-made gin with distilleries, vendors, food, music, and cocktails.
Official Website: https://oregonspiritdistillers.com
Munch & Music
Type: Music Festival
Location: Drake Park, Bend, OR
Month: July-August
Description: Free concert series with live music, food vendors, and family activities.
Official Website: https://www.munchandmusic.com/
Airshow of the Cascades Festival
Type: Airshow Festival
Location: Madras Municipal Airport, Madras, OR
Month: August
Description: Largest airshow in Oregon with acrobatic planes, jets, warbirds, and more.
Official Website: https://cascadeairshow.com
Bend Comedy Festival
Type: Comedy Festival
Location: Various locations, Bend, OR
Month: August
Description: Features national and local comedians in multiple events around town.
Official Website: https://www.bendcomedyfestival.com/
Bend Yoga Festival
Type: Yoga Festival
Location: Bend, OR
Month: June
Description: A festival dedicated to yoga with classes, workshops, and community events.
Official Website: https://www.bendyogafestival.com/
Big Ponderoo Music & Art Festival
Type: Music and Art Festival
Location: Village Green Park, Sisters, OR
Month: June
Description: Intimate festival featuring Americana and bluegrass music, with camping available.
Bend Summer Festival
Type: Arts and Culture Festival
Location: Downtown Bend, OR
Month: July
Description: Celebration of arts, culture, and community with art showcases, live music, and food.
Official Website: https://bendsummerfestival.com/
Fairwell Festival
Type: Music Festival
Location: Deschutes County Fairgrounds, Redmond, OR
Month: July
Description: Features folk, blues, rock, country, and soul music with over 36 performances.
Official Website: https://www.fairwellfestival.com/
Balloons Over Bend
Type: Hot Air Balloon Festival
Location: Bend, OR
Month: July
Description: Hot air balloon launches, night glow, and family-friendly activities.
Official Website: https://balloonsoverbend.com/
Deschutes County Fair and Rodeo
Type: Fair and Rodeo
Location: Deschutes County, OR
Month: July-August
Description: Annual county fair with rodeo events, exhibits, entertainment, and carnival rides.
Official Website: https://expo.deschutes.org/p/fair
Sunriver Music Festival
Type: Music Festival (Classical)
Location: Sunriver Resort, Sunriver, OR
Month: August
Description: Classical music festival with orchestra and soloist performances.
Official Website: https://www.sunrivermusic.org/
Art in the High Desert
Type: Art Festival
Location: Riverbend Park, Bend, OR
Month: August
Description: Fine art and craft festival featuring artists from across North America.
Official Website: https://www.artinthehighdesert.com/
Sisters Folk Festival
Type: Music Festival (Folk)
Location: Sisters, OR
Month: September
Description: Americana and roots music festival with multiple stages and artists.
Official Website: https://www.sistersfolkfest.org/
RendezVan Festival
Type: Music Festival
Location: Mt. Bachelor, Bend, OR
Month: May
Description: Festival celebrating van-life culture with music, food trucks, and outdoor activities.
Official Website: https://www.rendezvan.com/
4 Peaks Music Festival
Type: Music Festival
Location: Stevenson Ranch, Bend, OR
Month: June
Description: Music festival with camping, yoga, and family activities, featuring various genres.
Official Website: https://4peaksmusic.com/
Bend Roots Revival
Type: Music Festival
Location: Various venues, Bend, OR
Month: September
Description: Free, family-friendly music festival with diverse stages and local talent.
Official Website: https://bendroots.net/
Cascade Equinox Festival
Type: Music and Art Festival
Location: Deschutes County Fairgrounds, Redmond, OR
Month: September
Description: Festival with art installations, healing garden, and music performances.
Official Website: https://cascadeequinox.com/
Bend Fall Festival
Type: Fall Festival
Location: Downtown Bend, OR
Month: October
Description: Celebration of fall with artisans, live music, harvest market, and local food and drinks.
Official Website: https://bendfallfestival.com/
FairWell Festival
Type: Music (Country, Americana, Roots)
Location: Deschutes County Fairgrounds, Redmond, OR
Month: July
Description: A two-day music festival featuring country, Americana, and roots music with headliners like Tyler Childers and Sturgill Simpson. Known for its high-energy performances and growing popularity in the country music scene.
Official Website: https://fairwellfestival.com/
Balloons Over Bend
Type: Family/Outdoor
Location: RE Jewell Elementary & Riverbend Park, Bend, OR
Month: July
Description: A family-friendly festival featuring hot air balloon launches in the morning and captivating Night Glow events in the evening. Offers stunning views of balloons against the Cascade Mountains.
Official Website: https://www.balloonsoverbend.com/
Deschutes County Fair & Rodeo
Type: Fair/Rodeo
Location: Deschutes County Fairgrounds, Redmond, OR
Month: August
Description: Central Oregon’s largest annual event, featuring a championship rodeo, concerts, carnival rides, exhibits, and classic fair food. A five-day celebration of local culture and entertainment.
Official Website: https://expo.deschutes.org/events/2025/deschutes-county-fair-rodeo
Sunriver Music Festival
Type: Music (Classical, Pops)
Location: Sunriver Resort Great Hall & Tower Theatre, Bend, OR
Month: August
Description: A premier classical and pops music festival featuring world-class orchestra musicians and soloists. Held over several days with concerts and free public rehearsals.
Official Website: https://sunrivermusic.org/
Art in the High Desert
Type: Art/Craft
Location: Riverbend Park, Bend, OR
Month: August
Description: One of the West Coast’s top art shows, featuring a juried selection of fine art and craft.
Official Website: https://www.artinthehighdesert.com/
Bend Summer Festival
Type: Arts/Culture/Community
Location: Downtown Bend, OR
Month: July
Description: A vibrant celebration of arts, culture, and community with fine food, libations, talented artists, and live music across three stages. Draws nearly 40,000 attendees annually.
Official Website: https://bendsummerfestival.com/
Bend Fall Festival
Type: Autumn Celebration
Location: Downtown Bend, OR
Month: September/October
Description: A time-honored tradition featuring pumpkin painting, a Harvest Market, Family Play Zone, live music, and more. Celebrates the beauty of autumn in the Pacific Northwest.
Oregon WinterFest
Type: Winter Festival
Location: Old Mill District, Bend, OR
Month: February
Description: The Pacific Northwest’s largest winter festival, featuring live music, food, drink, and family activities along the Deschutes River. A celebration of winter in Central Oregon.
Bend Venture Conference
Type: Business/Entrepreneurship
Location: Various locations, Bend, OR
Month: October
Description: A two-day event uniting entrepreneurs and investors, celebrating Central Oregon’s startup community. Features over 65 innovative companies and has facilitated millions in investments.
Official Website: https://bendvc.com/
Harvest Faire
Type: Artisan/Craft
Location: Downtown Sisters, OR
Month: October
Description: A 40-year tradition in nearby Sisters, featuring artisan vendors, handcrafted items, local food, and live music. A great opportunity for holiday shopping and celebrating the season.
Official Website: https://www.sisterscountry.com/harvest-faire/