Planning around a Bend festival? This guide now separates what is still coming up in 2026 from dates that organizers have already confirmed for 2027, so you can use it both for near-term plans and next year's trips.
What is still coming up in 2026
As of September 23, 2026, the biggest remaining festival weekends are concentrated in late September and early October.
Sisters Folk Festival - September 25–27
The Sisters Folk Festival runs September 25–27, 2026 in downtown Sisters. Expect 30+ artists, multiple stages and intimate venues spread throughout town.
Best for: folk, roots and Americana; couples; and visitors who want to build a full weekend around Sisters.
Official festival: https://www.sistersfolkfest.org/
Bend Fall Festival - October 2–4
Downtown Bend’s Fall Festival runs October 2–4, 2026 with live music, art and makers, food, drinks and family activities.
- Friday, October 2: 5–10 p.m. - music and food only
- Saturday, October 3: 11 a.m.–10 p.m.
- Sunday, October 4: 11 a.m.–5 p.m.
Best for: families, casual live music, art browsing and a free downtown festival weekend.
Official festival: https://bendfallfestival.com/
Bend Film Festival - October 7–11
The 23rd Annual Bend Film Festival runs October 7–11, 2026 with screenings, filmmaker discussions, events and independent film programming around Bend.
Best for: film fans, date nights and a culture-focused Bend trip.
Official festival: https://bendfilm.org/festival/
2027 festival dates you can already plan around
Several major organizers have already published 2027 dates. That is unusually helpful this early, especially if you are planning lodging around a specific festival weekend.
Bend WinterFest - February 12–14, 2027
WinterFest is moving to a new location near The Pavilion in Bend for 2027. Organizers are also adding more ice programming in partnership with Bend Park & Recreation District.
Official festival: https://oregonwinterfest.com/
Bend Brews & Beyond - May 29, 2027
The third annual Bend Brews & Beyond is scheduled for May 29, 2027 in Drake Park, with Oregon breweries, cideries and non-alcoholic beverage makers.
Official festival: https://bendbrewsandbeyond.com/
Sisters Rodeo - June 9–13, 2027
Sisters Rodeo has already confirmed June 9–13, 2027. It is more rodeo than traditional festival, but it is one of Central Oregon’s biggest June destination weekends.
Official event: https://sistersrodeo.com/
Big Ponderoo - June 25–26, 2027
Big Ponderoo returns to Village Green Park in Sisters June 25–26, 2027. The organizer says the lineup and weekend passes will roll out later.
Official festival: https://www.bigponderoo.com/
Bend Summer Festival - June 25–27, 2027
Bend Summer Festival is currently showing June 25–27, 2027 for its free downtown arts, music, food and family weekend.
Official festival: https://bendsummerfestival.com/
Cascade Equinox - September 17–19, 2027
Cascade Equinox was postponed out of 2026 and is now scheduled to return September 17–19, 2027 at the Deschutes County Fairgrounds in Redmond.
Official festival: https://cascadeequinox.com/
Still waiting on 2027 dates
We have not found official 2027 dates yet for every recurring event. BendFilm, Sisters Folk Festival, Bend Roots Revival, Bend Oktoberfest, Balloons Over Bend, Munch & Music and several others still need their 2027 schedules published.
We will add those as organizers release them rather than projecting dates from prior years.
The complete 2026 Bend & Central Oregon festival calendar
Full 2026 calendar at a glance
This calendar focuses on actual festivals and major recurring community celebrations, not every 5K, expo, concert or farmers market in Central Oregon. That keeps it useful instead of turning it into an endless event dump.
| Month | Festival | 2026 dates | Location |
|---|---|---|---|
| February | Bend WinterFest | Feb. 13–15 | Bend |
| March | Winter PrideFest | Mar. 5–8 | Bend / Mt. Bachelor |
| May | Bend Brews & Beyond | May 23 | Drake Park |
| May | Bend Summer Festival | May 29–31 | Downtown Bend |
| June | Sisters Rodeo | June 10–14 | Sisters |
| June | Bend Yoga Festival | June 11–14 | Bend |
| June | Big Ponderoo | June 26–27 | Sisters |
| July–August | Munch & Music | Thursdays July 2–Aug. 6 | Drake Park |
| July | Balloons Over Bend | July 24–26 | Bend / Redmond |
| August | The Little Woody | Aug. 29 | Bend |
| September | Bend Comedy Festival | Sept. 4–6 | Bend |
| September | Bend Roots Revival | Sept. 11–13 | Bend |
| September | Bend Oktoberfest | Sept. 19 | Bend |
| September | Oregon Whiskey Festival | Sept. 19–20 | Bend |
| September | Sisters Folk Festival | Sept. 25–27 | Sisters |
| October | Bend Fall Festival | Oct. 2–4 | Downtown Bend |
| October | Bend Film Festival | Oct. 7–11 | Bend |
Major festivals from earlier in 2026
These earlier 2026 events stay on the page as a reference. When an organizer has already published a 2027 date, we call that out above instead of guessing from the prior-year weekend.
Bend WinterFest - February 13–15
WinterFest ran President’s Day weekend with outdoor entertainment, art, food and drinks. Official 2026 hours were Friday 5–10 p.m., Saturday 11 a.m.–10 p.m. and Sunday 11 a.m.–5 p.m. The event is outdoors, so winter layers matter.
https://oregonwinterfest.com/
Winter PrideFest - March 5–8
OUT Central Oregon’s Winter PrideFest combined mountain activities with drag, dancing, comedy and community events around Bend. The 2026 schedule included events at Mt. Bachelor, UPP Liquids, Midtown Ballroom, Silver Moon Brewing and other venues.
https://www.winterpridefestcentraloregon.com/
Bend Brews & Beyond - May 23
The 2026 festival took place in Drake Park with Oregon breweries, cideries and other beverage makers, food and live entertainment. The organizer has already moved its website forward to 2027, so do not mistake the current homepage’s future date for the 2026 event.
https://bendbrewsandbeyond.com/
Bend Summer Festival - May 29–31
One of downtown Bend’s biggest free annual events. The 2026 festival featured more than 80 regional and national artisans, live music, food, family programming and shopping throughout the downtown core.
https://bendsummerfestival.com/
Sisters Rodeo - June 10–14
“The Biggest Little Show in the World” is more rodeo than traditional festival, but it is too important to Central Oregon’s June calendar to leave out. The 2026 PRCA event ran June 10–14 in Sisters.
https://sistersrodeo.com/
Bend Yoga Festival - June 11–14
The 2026 festival ran Thursday through Sunday with nearly all venues in downtown Bend, including the Oxford Hotel ballroom, Pine & Prism Wellness, Boys & Girls Club and Yoga Shala Bend.
https://www.bendyogafestival.com/
Big Ponderoo - June 26–27
SFF Presents’ summer music and arts festival brought a smaller, relaxed festival experience to Village Green Park in Sisters. The official site has already rolled over to its June 25–26, 2027 dates, but archived 2026 organizer pages confirm June 26–27 for this year’s event.
https://www.bigponderoo.com/
Munch & Music - July 2 through August 6
Bend’s long-running free Thursday concert series celebrated its 35th season in Drake Park. The 2026 dates were July 2, 9, 16, 23 and 30 plus August 6, with music, Restaurant Row, a Kids Zone, artisan vendors and libations.
https://www.munchandmusic.com/
Balloons Over Bend - July 24–26
Hot-air balloon launches took place around sunrise, with the Bend Night Glow and Redmond Night Glow adding evening events. Balloon events are especially weather-dependent, so this is one to check the morning of even when the dates are confirmed.
https://balloonsoverbend.com/
The Little Woody - August 29
2026 was not just another Little Woody. It was the final event. “The Last Woody” ran one day only, Saturday, August 29 from noon–9 p.m. The organizer explicitly confirmed that 2026 was the last edition, so old listings showing a two-day 2026 festival are outdated.
https://thelittlewoody.com/
What changed in Bend’s 2026 festival calendar?
2026 was the final Little Woody
The Little Woody’s own FAQ confirms that the August 29 event was the last edition and that 2026 was a one-day festival. If you are planning ahead for 2027, do not assume it will return on its traditional late-August weekend.
Some festival websites roll forward before the year is over
This is why festival guides get stale so quickly. Big Ponderoo and Bend Brews & Beyond, for example, have already started promoting 2027. We preserve confirmed 2026 dates here while linking to the organizer so you can see the newest information.
Best Bend festivals by what you actually want to do
Best free festivals
- Bend Roots Revival - free, huge variety of local music
- Bend Summer Festival - free downtown arts, music and family programming
- Bend Fall Festival - free fall weekend downtown
- Munch & Music - free Thursday concerts in Drake Park
Best music festivals
- Sisters Folk Festival - best destination music festival
- Bend Roots Revival - best for discovering Central Oregon artists
- Big Ponderoo - smaller outdoor festival feel in Sisters
- Munch & Music - easiest free summer option
Best food and drink festivals
- Bend Oktoberfest - classic fall beer-festival energy
- Oregon Whiskey Festival - focused Oregon spirits tasting
- The Little Woody - barrel-aged beer tradition; 2026 was the final event
- Bend Brews & Beyond - spring beer and beverage festival
For year-round brewery ideas, see our Bend brewery guide.
Best family-friendly festivals
- Bend Summer Festival
- Bend Fall Festival
- Bend Roots Revival
- Balloons Over Bend
- Munch & Music
Always check the organizer’s age rules for specific stages, beer gardens or evening events. A festival can be family-friendly overall while individual venues are 21+.
Best arts and culture festivals
- Bend Film Festival - independent film and filmmaker events
- Bend Summer Festival - art and makers throughout downtown
- Bend Fall Festival - art, live demonstrations, music and food
- Sisters Folk Festival - intimate performance spaces throughout town
How to plan a festival weekend in Bend
Pick one geographic area
Bend is easy to navigate on a normal weekday. A festival, amphitheater show and a busy summer weekend can change that quickly.
- Downtown: walk between Fall Festival, BendFilm venues, restaurants and bars.
- Drake Park: walk or bike when possible for Munch & Music and park-based events.
- Sisters: treat Sisters Folk Festival or Big Ponderoo as a destination day rather than an add-on between Bend activities.
- Mt. Bachelor / winter events: check road conditions before leaving town.
See our things to do in Bend guide if you need activities around your festival plans.
Book lodging around the festival, not the other way around
The weekends that create the most pressure on lodging are usually the major summer festivals, holiday weekends and Sisters destination events. If the festival is the reason for your trip, lock in the room before building dinner reservations and hikes around it.
Do not assume parking will be easy
For downtown and Drake Park events, walking and biking are often easier than circling for the perfect parking spot. If you are drinking, plan a rideshare or designated driver before the event starts.
Check smoke and weather
Central Oregon festival season spans February snow through August heat and September wildfire smoke.
Before an outdoor festival, check:
- event organizer updates
- current Bend weather
- air quality and wildfire smoke
- road conditions if driving from Sisters, Redmond or the mountains
Balloons Over Bend is particularly weather-sensitive because safe balloon launches depend on conditions around sunrise.
Bring the right festival setup
Rules vary. Some events allow low-back chairs and blankets; others do not. Some welcome kids but not pets. Some are entirely 21+.
Before you go, check the event FAQ for:
- bag policy
- outside food and drink rules
- chair or blanket rules
- pet policy
- re-entry
- cash vs. card
- accessibility
Easy Bend festival weekend itineraries
Free music weekend
Bend Roots Revival → dinner downtown → another stage or venue → slow breakfast → Deschutes River Trail the next morning.
Fall festival weekend
Morning coffee downtown → Bend Fall Festival → lunch from a festival vendor → break at the hotel → dinner/drinks downtown → easy hike or High Desert Museum the next day.
Sisters music weekend
Drive to Sisters early → coffee and walk downtown → festival performances → dinner in Sisters → stay locally if possible → return to Bend the following day rather than commuting back and forth repeatedly.
BendFilm weekend
Late breakfast → afternoon screening → coffee or dinner downtown → evening screening/event → brunch and one short outdoor activity the next morning.
Frequently asked questions about Bend festivals
What are the biggest festivals in Bend, Oregon?
Some of the most established and popular annual events include Bend Summer Festival, Bend Fall Festival, BendFilm, Bend WinterFest, Balloons Over Bend and the Munch & Music series. Bend Roots Revival and the Bend Comedy Festival are also major September draws.
What festivals are still happening in Bend in late September 2026?
As of September 23, the biggest remaining September festival is Sisters Folk Festival, running September 25–27 in nearby Sisters.
What festivals are happening in Bend in October 2026?
Bend Fall Festival is October 2–4 and Bend Film Festival is October 7–11. Those are the two biggest festival-style events in Bend on the confirmed October calendar.
Are Bend festivals free?
Some are. Bend Summer Festival, Bend Fall Festival, Bend Roots Revival and Munch & Music are strong free options. Music festivals such as Sisters Folk Festival and events such as BendFilm, WinterFest and Bend Comedy Festival generally require tickets or passes.
When is Cascade Equinox coming back?
Cascade Equinox is scheduled to return September 17–19, 2027 at the Deschutes County Fairgrounds in Redmond.
Is The Little Woody coming back in 2027?
The organizer says 2026 was the final Little Woody, so we would not plan on a 2027 edition unless the organizers make a new announcement.
Where can I find smaller Bend events too?
For concerts, workshops, markets and one-off events that do not belong on this festival list, use our Bend events calendar. This page is intentionally focused on major festivals so it stays useful and easy to scan.
We update this guide as organizers confirm dates, cancel events or roll their calendars into the next year. If an official organizer changes a date, the organizer’s own page should always win.
