Festivals in Bend, Oregon (And Nearby Areas) 2025 & 2026
There’s something about a festival in Central Oregon that just hits different. Maybe it’s the way the Cascade peaks catch the sunset behind the stage. Or how the Deschutes River winds its way past the crowds in Drake Park. Maybe it’s because we’ve got a little bit of everything here—beer lovers, artists, mountain bikers, dog parents, families, vanlifers, folks who’ve been here 30 years, and folks who moved here last month.
Bend knows how to do festivals right. So do our neighbors in Redmond, Sisters, Sunriver, and the rest of Central Oregon. This guide gives you the full picture: what to expect, how to plan, and what makes our festival scene worth showing up for all year long.
Table of Contents
Upcoming festivals in & around Bend
Sunriver Music Festival (August 2–13, 2025)
A multi-day classical music festival featuring world-class musicians, orchestral concerts, and casual performances in scenic Central Oregon settings.
Focused on classical and orchestral music
Family-friendly concerts and music education programs
Venues include both indoor and outdoor locations in Sunriver and Bend
Great for music lovers of all ages
More info:
https://www.oldmilldistrict.com/bend-events/festivals/
Art in the High Desert (August 22–24, 2025)
A juried fine art and craft show held along the banks of the Deschutes River. Showcasing work from over 100 artists from across the U.S. and Canada.
High-quality, juried fine art event
Free to attend
Takes place in the Old Mill District near the river
Great for browsing and buying handmade art, jewelry, ceramics, and more
More info:
https://www.oldmilldistrict.com/bend-events/festivals/
The Little Woody (August 29–30, 2025)
A celebration of barrel-aged beers, ciders, and whiskey, spotlighting rare brews and small-batch spirits from the Northwest.
21+ only event
Features limited-release and specialty barrel-aged drinks
Live music, food vendors, and a fun beer garden vibe
Held at the Deschutes Historical Museum grounds
More info:
https://www.oldmilldistrict.com/bend-events/festivals/
Reggae Rise Up Oregon (August 29–31, 2025)
A high-energy reggae music festival bringing national and international artists to the Deschutes County Fairgrounds in Redmond. Expect three days of live music, art installations, and a full festival atmosphere.
All-ages event
Features top reggae acts, food vendors, and immersive art
Camping available on-site for a complete festival experience
Gates typically open mid-day, with music into the evening
More info:
https://reggaeriseup.com/oregon/
Bend Comedy Festival (August 29–31, 2025)
A nonprofit celebration of stand-up comedy, community, and creativity over Labor Day Weekend in Bend. Brings together national headliners, breakout talent, and Oregon’s best local comedians.
20+ shows across downtown venues like Midtown Ballroom, Volcanic Theatre Pub, and Silver Moon Brewing
All-ages and 21+ shows available
Mix of big-name comics and emerging talent
Focus on building Bend’s arts and comedy scene
More info:
https://www.bendcomedyfestival.com/
Cascade Equinox Festival (September 19–21, 2025)
A multi-genre music and arts festival held at the Deschutes County Fairgrounds. Combines live performances, interactive art, workshops, and a vibrant community vibe.
Family-friendly with kids’ activities and workshops
On-site camping available
Includes live art, yoga, and diverse food options
Known for its welcoming, inclusive atmosphere
More info:
https://cascadeequinox.com/
Oregon Whiskey Festival (September 19–20, 2025)
A celebration of Oregon-made whiskey, featuring tastings from over 20 distilleries, live music, gourmet food, and educational sessions.
VIP Experience includes exclusive Friday night event, early Saturday entry, VIP lounge, and special cocktails
General Admission includes Saturday entry, commemorative tasting glass, and 8 taster tokens
Outdoor event, rain or shine
Live music, food trucks, and whiskey cocktails available
More info:
https://oregonwhiskeyfestival.com/
Sisters Folk Festival (September 26–28, 2025)
A beloved Americana music festival set across multiple intimate venues in downtown Sisters. Features folk, bluegrass, blues, and singer-songwriter performances.
Venues include tents, churches, and small stages throughout Sisters
Three-day pass grants access to all shows
Known for its warm, small-town community feel
Attracts nationally recognized and up-and-coming artists
More info:
https://sistersfolkfestival.org/
Bend Fall Festival (October 3–5, 2025)
A downtown Bend tradition celebrating the season with local food, live music, and family activities.
Free to attend
Features local art vendors, harvest-themed food, and beer/wine gardens
Kids’ Harvest Area with games and crafts
Multiple music stages with regional bands
More info:
https://bendfallfestival.com/
Bend Film Festival (October 8–12, 2025)
A five-day celebration of independent film, showcasing screenings, panels, and filmmaker Q&As in various venues around Bend.
Features films from around the world
Opportunities to meet and interact with filmmakers
Screenings at multiple downtown theaters and pop-up venues
Includes award ceremonies and after-parties
More info:
https://bendfilm.org/
Halloween in the Old Mill District (October 31, 2025)
A family-friendly Halloween celebration with trick-or-treating at Old Mill District shops and restaurants.
Free event for kids and families
Runs in the afternoon and early evening
Costumes encouraged for all ages
Participating businesses hand out candy
More info:
https://www.oldmilldistrict.com/
Bend Design (November 7–8, 2025)
A two-day creative conference that brings together designers, artists, and innovators for talks, workshops, and networking.
Hosted by Scalehouse in Bend
Features keynote speakers, panels, and hands-on sessions
Open to creative professionals and curious minds alike
Held at OSU–Cascades with nearby Old Mill access
More info:
https://www.scalehouse.org/benddesign
Bend Winter Fest (February 13–15, 2026)
A winter celebration in Bend featuring live music, ice carving, wine walks, rail jams, and family fun.
Held in the Old Mill District
Multiple music stages with local and regional acts
Marketplace with local vendors and food trucks
Activities for all ages, from kids’ zones to beer gardens
More info:
https://oregonwinterfest.com/
Likely Returning in 2026
Balloons Over Bend (Likely Returning in 2026)
Hot air balloons fill the Bend skyline at sunrise, followed by a night glow event. Family activities, food, and live entertainment included.
More info:
https://balloonsoverbend.com/
Munch & Music (Likely Returning in 2026)
A free summer concert series in Bend’s Drake Park featuring live music, food vendors, and a beer garden.
More info:
https://www.munchandmusic.com/
Bend Summer Festival (Likely Returning in 2026)
Downtown Bend’s signature summer street festival with live music, local art vendors, and family-friendly activities.
More info:
https://bendsummerfestival.com/
FairWell Festival (Redmond) (Likely Returning in 2026)
A major summer music festival at the Deschutes County Fairgrounds featuring multiple stages, national headliners, and camping options.
More info:
https://www.fairwellfestival.com/
4PEAKS Music Festival (Likely Returning in 2026)
An intimate multi-day camping and music festival in Bend showcasing a wide range of genres with a focus on community and connection.
More info:
https://4peaksmusic.com/
Why Festivals in Bend Feel So Local (Even When They’re Not)
We’ve got a deep-rooted sense of community in Bend, and that shows up at just about every event. Even the big-name music fests still feel down-to-earth. You'll run into the same food trucks that post up on Galveston every weekend. Artists you bought earrings from at a First Friday pop-up. The local brewery who made a special batch just for this event.
It’s not just about showing up—it’s about celebrating what makes this place special.
Festivals here are also pretty personal. Small enough to feel connected, big enough to feel exciting. It’s not LA. It’s not Portland. It’s Bend—and it’s got its own rhythm.
What to Expect at Central Oregon Festivals
Every town around here has its own flavor, but most festivals across the region have a few things in common. If it’s your first time heading out, or if you just want to plan better, here’s what to know:
Dog-Friendly (Usually)
You’ll see leashes everywhere. Most festivals allow dogs, but use your judgment—midday pavement gets hot and not all dogs love loud crowds. Some events even have dog water stations and treat booths.
Family-Friendly But Still Fun for Adults
Events are designed to keep all ages entertained. That means bounce houses and face painting next to craft cocktail stations and beer tents. The kids have their zone. So do you.
Outdoors is the Norm
We live outside as much as we can. Expect grassy parks, dirt trails, river views, and the occasional dust storm. Sunscreen is essential. Hats help. And layers are your best friend.
Food and Drink Are a Big Deal
You’re not getting freezer-burned corn dogs here. Most festivals in Bend bring out the best in local eats: smoked meats, vegan fusion, craft sodas, and plenty of Bend-brewed beer. Kombucha and cold brew usually make an appearance too.
Bend Time is a Thing
We’re not in a rush. Schedules shift, lines move slow, and things don’t always go perfectly—but folks are usually too happy to care. Be patient and enjoy the moment.
The Festival Season in Bend: Month-by-Month Energy
Every time of year has its own feel. Here’s a breakdown of what to expect depending on when you're in town.
Spring (March–May)
Spring is when we thaw out. Events are smaller but start to pick up speed. Think seed swaps, art fairs, early farmer’s markets, and Earth Day celebrations. People are just excited to be outside again without snow boots. You'll see lots of flannel and fleece, and usually some wind.
It's also when cycling and outdoor sports fests kick off. Trails start drying out, and that means mountain bike events, 10Ks, and more community wellness gatherings like yoga festivals or outdoor meditation days.
Best part? Fewer crowds and easier parking before the summer rush.
Summer (June–August)
This is when Bend booms. Practically every weekend has something going on. Drake Park turns into a festival hub, the Old Mill comes alive with big shows, and downtown closes streets for block parties and beer walks.
You’ll find food and drink festivals, river floats tied to concerts, outdoor movies, and multi-day music events that turn into all-out campouts. Redmond’s Deschutes County Fairgrounds host major headliners, while Sisters turns into a hub for folk music and western heritage.
Summer weather here is unreal—warm days, cool nights, and almost no rain. It’s prime time, so book early and bring patience with the crowds. Most events are casual, but sun protection, hydration, and a camp chair will make your life way better.
Fall (September–November)
Fall is sneakily one of the best times for festivals in Central Oregon. The leaves turn, the air is crisp, and it’s harvest season. That means cider tastings, Oktoberfests, pumpkin patches, and apple-themed everything.
A lot of food and drink festivals peak in September. Outdoor markets are still running strong, and concerts continue until the nights get too cold. You’ll also see more intimate indoor gatherings—poetry slams, film festivals, local maker fairs, and small concerts at places like The Belfry in Sisters or Volcanic Theatre Pub in Bend.
This season feels more mellow, more local, and a little less crowded—just how we like it.
Winter (December–February)
You might think festival season dies in the winter. Not around here. We bundle up and keep going.
You’ll find light displays, holiday markets, winter solstice celebrations, and fire pits set up at outdoor venues with hot toddies in hand. Sunriver leans into holiday events with sleigh rides and tree lightings, while Mt. Bachelor hosts snow-centric festivals with live DJs, ski races, and themed parties.
It’s also when craft markets thrive. Locals come out for winter art shows, holiday gift fairs, and cozy cabin-style pop-ups. And if you're into winter sports, there's always something happening on the mountain—official or unofficial.
Festival Tips from Locals
A little insider advice goes a long way. Here are some things folks from around here know to do:
Bring a blanket or camp chair: Sitting on the ground is fine—until you realize it's damp or pokey.
Stash a reusable water bottle: Most festivals have refill stations, and you’ll save a few bucks staying hydrated.
Pack layers: Even on the hottest summer days, evenings cool down fast.
Ride your bike: Bike valets are common, and you'll avoid the nightmare of downtown parking.
Pick your spot early: At Drake Park or the amphitheater, prime spots go fast. Send a friend with a blanket to stake it out.
Watch the altitude: We’re over 3,500 feet up. If you’re not used to that, drinks can hit harder and sunburns show up quicker.
Cash isn’t dead: Most vendors take cards, but not all. It doesn’t hurt to keep a twenty or two in your bag.
Ask a volunteer: Most events are powered by locals giving their time. They usually know the lay of the land and can point you in the right direction.
Nearby Towns That Throw a Great Festival
Don’t stop at Bend. A quick drive can land you at some of the best festivals in the region:
Redmond
Redmond’s come into its own lately. There’s a blend of old-school county fair charm and a newer creative energy. You’ll find rodeos, car shows, BBQ competitions, and big-scale events out at the Deschutes County Fair & Expo Center. It feels a little more laid-back than Bend but just as fun.
Sisters
Sisters has a deep creative pulse. The town leans into its western aesthetic, but don’t let that fool you—its festivals draw national talent. The Sisters Folk Festival is iconic. There’s also a massive quilt show that literally covers the town in fabric. Art walks, poetry readings, and bluegrass are part of the regular rotation.
Sunriver
Sunriver’s got a more resort-style vibe, but families love it. A lot of events are centered around the Village at Sunriver and appeal to younger kids, with themed holiday events, nature festivals, and seasonal happenings that feel like classic Americana. Think Fourth of July bike parades, tree lighting ceremonies, and winter bonfires.
