Festivals in Bend, Oregon (And Nearby Areas) 2025 & 2026
Updated 12/5/25
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 in 2026
Cascades Wedding Show (Jan 17, 2026)
The Cascades Wedding Show is a one‑day bridal event hosted at the Riverhouse on the Deschutes. It features bridal vendors, a wedding fashion show and live music, making it a one‑stop resource for couples planning their big day. Visitors can also enter giveaways and collect swag bags filled with wedding planning goodies.
Date & time – January 17 2026 from 10 a.m. to 3 p.m. at the Riverhouse Lodge & Conference Center in Bend.
Focus – This show highlights local photographers, florists, caterers and planners, plus a live wedding fashion show and music showcase.
Extras – Admission includes a swag bag, a chance to find a golden ticket good for prizes, and entry into giveaways for honeymoon packages and more.
Tickets – Tickets may be purchased online or at the door; early buyers can often score discounts.
Audience – Couples planning weddings, along with friends and family members looking for ideas and vendors.
Location – Riverhouse Lodge & Conference Center, 3075 N Business 97, Bend, OR.
Info – Details, including vendor list and fashion show schedule, are posted on the show’s website.
Bend WinterFest (Feb 13‑15, 2026)
Bend WinterFest is a large winter celebration held at the Deschutes County Expo Center. Over three days it combines outdoor sports events with live music, art installations and family activities. The festival includes night-time fire pits, snow and ice sculptures, a wine walk and craft beer garden, providing a warm atmosphere despite February temperatures.
Dates & hours – Friday Feb 13 (5–10 p.m.), Saturday Feb 14 (11 a.m.–10 p.m.) and Sunday Feb 15 (11 a.m.–5 p.m.)
Highlights – Live music on the main stage, a jaw‑dropping fire-breathing performance, ice-carving exhibitions, a ski‑and‑snowboard Pump Bump competition and a family ice- and snow-play zone.
Food & drink – Bend WinterFest features a wine walk, beer garden and food carts serving winter comfort foods.
Art & marketplace – Local artisans display and sell their work, and the festival builds a winter wonderland with light installations and fire pits.
Family friendly – Activities include a kids’ zone with snow play, games and supervised crafts.
Parking – Held at the Deschutes County Fairgrounds in Redmond, which offers ample parking; shuttles usually operate from Bend.
Tickets – Admission passes are typically sold per day or for the full weekend, with kids aged 12 and under admitted free.
Hot Cocoa Run (Feb 15, 2026)
Part of WinterFest weekend, the Hot Cocoa Run is a short 5 k run/walk along paved paths near the Deschutes River. It celebrates winter fitness and ends with a complimentary cup of cocoa.
Date & time – February 15 2026 (race start usually around 9 a.m.).
Distances – 5 k run/walk; many participants wear festive winter attire.
Rewards – Finishers receive a commemorative mug and a cup of cocoa.
Location – Typically runs through the Old Mill District or near the Deschutes County Expo Center.
Registration – Sign up online; entry includes a WinterFest day pass.
Family friendly – Open to all ages and abilities with stroller-friendly course.
Charity – A portion of proceeds often benefits local youth sports or health charities.
Contact – Details at WinterFest or the Lay It Out Events site.
https://runsignup.com/Race/OR/Bend/BendWinterFestHotCocoaRun
Winter PrideFest (Mar 5‑8, 2026)
Winter PrideFest celebrates the LGBTQ+ community and allies with a long weekend of skiing, riding and social events around Bend. Organized by OUT Central Oregon, it has grown from 150 participants in 2018 to more than 2,400 in 2025winterpridefestcentraloregon.com. The 2026 festival is scheduled for March 5 – 8, with events at Mount Bachelor and venues in downtown Bend.
Dates – March 5 – 8 2026winterpridefestcentraloregon.com.
Activities – Alpine skiing and snowboarding days at Mt. Bachelor, Nordic skiing and snowshoe outings, drag tubing and a drag show, après‑ski parties, and a downtown Pride celebration.
Inclusivity – The festival is open to all and aims to celebrate inclusivity, Pride and outdoor adventurewinterpridefestcentraloregon.com.
Growth – Participation has increased substantially, with the 2025 festival drawing over 2,400 peoplewinterpridefestcentraloregon.com.
Venues – Events are held at Mount Bachelor, the Tower Theatre and several downtown bars and clubs.
Tickets – Weekend passes and individual event tickets are sold; early purchase is recommended because many events sell out.
Beneficiary – Proceeds support OUT Central Oregon and local LGBTQ+ initiatives.
Stay informed – The festival site encourages visitors to subscribe for updates as the full schedule will be released closer to the eventwinterpridefestcentraloregon.com.
Salmon Run (Apr 18, 2026)
One of Bend’s oldest running events, the Salmon Run celebrates the spring migration of salmon in the Deschutes River. Participants enjoy views of the river canyon while choosing from several distances.
Date – April 18 2026
Distances – Half marathon, 10 k and 5 k options are available
Course – Loops along paved and gravel paths through the Deschutes River Trail, with some gentle climbs
Finishers – All runners receive a finisher medal; awards are presented to overall and age‑group winners
Start & finish – Starts near the First Street Rapids Park and finishes at the same location; parking is available along Revere Avenue.
Family friendly – Stroller‑friendly course with an optional kids’ run.
Registration – Online sign‑up includes timing chip, aid stations and post‑race refreshments.
Beneficiary – A portion of proceeds benefits local river restoration projects.
Bend Brews & Beyond (Bend Brewfest) (May 23, 2026)
Bend Brews & Beyond – also referred to as the Bend Brewfest – returns to Drake Park for its second year in 2026. The festival brings together beer, cider and non‑alcoholic beverage producers for a one‑day celebration with live music and food trucks.
Date & time – Saturday, May 23 2026 from noon to 8 p.m.
Drink lineup – More than 50 Oregon breweries, cideries and beverage makers pour craft beer, cider, kombucha and other drinks
Meet the Makers – A mid‑afternoon “Meet the Makers” session allows attendees to chat with brewers and cidermakers about their creations
Brewers Decathlon & contests – The festival hosts a Brewers Decathlon (think cornhole, beer‑slinging and other goofy competitions) and the Bend Drinking Pants Pageant for best beer-themed outfit
Music & food – Local bands perform throughout the day; 10 food trucks offer tacos, pizza, BBQ, vegan fare and more
21 + event – Attendees must be 21 or older; ID required at entry
Tickets – Festival passes include a tasting glass and tokens for samples; additional tokens are available for purchase.
Location – Drake Park, Downtown Bend.
Getting there – Encourages biking or floating to the event; free bike and tube parking is provided
Happy Girls Run – Bend (May 9, 2026)
The Bend edition of the Happy Girls Run is part of a women‑focused race series. Runners enjoy scenic courses around Bend and a supportive atmosphere aimed at encouraging women of all ages and running backgrounds.
Date – May 9 2026
Distances – Half marathon, 10 k and 5 k courses
Course – Routes take runners through neighborhoods and natural areas near the Deschutes River, with aid stations every few miles
Swag – Participants receive custom technical shirts or sweatshirts, finisher medals and other race swag
Post‑race party – Finishers gather at the Old Mill District for live music, drinks and recovery treats.
Community – Designed to support women runners; pacers help first-time half‑marathoners.
Charity – A portion of proceeds supports local women’s health and education programs.
Packet pickup – Held the day before at a local running store.
Bend Yoga Festival (Jun 11‑14, 2026)
The Bend Yoga Festival is a four‑day wellness event that blends yoga classes with outdoor adventure, mindfulness workshops and community gatherings. It takes place outdoors at Miller’s Landing park and various indoor studios throughout Bend.
Dates & times – June 11 – 14 2026, with sessions running roughly 9 a.m. to 2 p.m. each day
Setting – Classes occur on riverfront lawns at Miller’s Landing and in downtown venues
Programming – The festival features world‑class yoga instructors, meditation and breathwork sessions, live music, art installations and community talks
Outdoor adventure – Passes often include optional river floats, hikes or paddleboarding excursions to complement the yoga practice.
Inclusivity – Designed for all skill levels; there are beginner, intermediate and advanced classes.
Sustainability – Organizers emphasize environmental stewardship and mindfulness about the land, including a land acknowledgement
Tickets – Single‑day, multi‑day and VIP passes available; early bird discounts offered.
Community – Encourages connection through group meditations and social events.
Conquer the Canyon (Jun 06, 2026)
This scenic race at Dry Canyon Trail in Redmond offers multiple distances and stunning views of sheer volcanic cliffs. Runners and walkers enjoy the option to bring their dogs to the 5 k Doggie Dash.
Date – June 6 2026
Distances – Half marathon, 10 k, 5 k and a 5 k Doggie Dash
Course – The race follows Redmond’s Dry Canyon Trail, a paved path flanked by steep canyon walls and desert vegetation
Dog-friendly – Leashed dogs are welcome in the Doggie Dash; participants receive a bandana and dog treat bag.
Awards – Finisher medals are given to all runners; age-group awards and special prizes for doggie participants.
Start & finish – Race headquarters at American Legion Park; plenty of parking nearby.
Post‑race – Enjoy music, vendors and refreshments in the park.
Registration – Online sign-up; early registration discounts available.
Sisters Rodeo (Jun 10‑14, 2026)
Known as the “Biggest Little Show in the World,” the Sisters Rodeo has entertained spectators since 1941. The 2026 event features five days of professional rodeo action along with a parade and community celebrations.
Schedule – The rodeo runs June 10 – 14 2026. Day one (June 10) hosts the PRCA Xtreme Bulls competition; day two (June 11) begins with breakfast concessions and Slack followed by a 7 p.m. PRCA sanctioned rodeo. Day three (June 12) hosts a 7 p.m. rodeo; day four (June 13) includes a morning parade through downtown Sisters and afternoon and evening performances; day five (June 14) features a Buckaroo Breakfast, Cowboy Church service and final rodeo at 1 p.m.
Events – Competitions include bull riding, bronc riding, barrel racing, roping and steer wrestling.
Parade – A Saturday morning parade through Sisters features floats, horses and marching bands
Family activities – Kid-friendly events such as mutton busting and stick horse races are part of the program.
Venue – Sisters Rodeo Grounds on Highway 20.
Tickets – Tickets sell out quickly; the website warns against buying from third‑party sellers
Parking & lodging – On-site parking with shuttles; nearby RV parks and campgrounds fill fast.
Community – Celebrated by locals and visitors, the rodeo funds scholarships and youth programs.
Big Ponderoo (Jun 26‑27, 2026)
Presented by the Sisters Folk Festival organization, Big Ponderoo brings a small‑town vibe and world‑class music to downtown Sisters. The 2026 festival is set for June 26 – 27, promising two days of roots, Americana and bluegrass.
Dates – June 26 – 27 2026
Music – Curated lineup of bluegrass, Americana and country artists performing on outdoor stages.
Atmosphere – Relaxed and family friendly; attendees are encouraged to bring camp chairs and picnic blankets
Location – Held in downtown Sisters with a backdrop of the Three Sisters peaks.
Tickets – Early bird passes typically go on sale in winter; discounted pricing available.
Vendors – Food trucks, craft beer and local artisans line the grounds.
Kids – Activities for children and a community art area.
Organizer – Produced by the nonprofit Sisters Folk Festival Inc.
Note – Big Ponderoo replaced Sisters’ June bluegrass festival and has quickly gained a following.
Bend Summer Festival (May 30‑31, 2026)
Central Oregon’s longest‑running arts and crafts festival sprawls across seven blocks of downtown Bend. The festival includes multiple music stages, juried art booths, food and libation vendors and a kids’ zone. According to its 2026 vendor listing, artist hours will run May 30 (11 a.m.–8 p.m.) and May 31 (11 a.m.–5 p.m.)
Dates & hours – May 30 – 31 2026 with artist booths open 11 a.m. to 8 p.m. Saturday and 11 a.m. to 5 p.m. Sunday
Art & crafts – More than 150 artists sell handmade jewelry, ceramics, painting, woodwork and photography
Music stages – Several stages feature regional and national acts spanning rock, jazz, soul and blues
Family fun – The festival includes a Family Play Zone with games and activities for kids.
Oregon Lifestyle area – Vendors showcase sustainable products, outdoor gear and local services.
Food & drink – A wide range of food carts and beer gardens provide meals, snacks and libations.
Admission – Free to attend; purchases and beverages cost extra.
Parking – Downtown parking fills quickly; walking, biking or ride-share is recommended.
Website – Event details and performer lineup posted closer to spring.
Munch & Music (July – Aug 2026)
A summertime tradition for more than three decades, Munch & Music is a free weekly concert series held on Thursday evenings in Bend’s Drake Park. 2025 marked the 34th season; the series is expected to return in 2026 with six weeks of music, food and community fun.
Dates – Thursday evenings in July and early August (exact 2026 dates TBD). Past series have run from early July through the first week of August
Format – Free concerts begin around 5:30 p.m. and end by 9 p.m., with two bands performing each night
Food & libations – Restaurant Row features numerous local food trucks; a Deschutes Brewery Libation Station pours beer, wine and cocktails
Kid zone – A large children’s area offers games, crafts and inflatables
Artisan row – Local artisans sell handmade items; businesses sponsor booths and giveaways.
Dog policy – Dogs are discouraged due to crowds
Location – Drake Park in downtown Bend with lawns along the Deschutes River
Admission – Free; bring low-back chairs or blankets and enjoy picnic-style seating.
Parking – On-street parking near downtown; biking is encouraged.
Sisters Outdoor Quilt Show (Jul 11, 2026)
For one day each July, the town of Sisters becomes the world’s largest outdoor quilt gallery. More than 1,300 quilts from around the globe adorn buildings and fences in downtown Sisters during this free festival.
Date & time – July 11 2026 from 9 a.m. to 4 p.m.
Scale – Over 1,300 quilts are displayed across the town, drawing quilters and art lovers from around the world
Admission – The show is free to attend
Venue – Quilts hang on buildings, store fronts and even the lampposts throughout downtown Sisters.
Workshops – Quilting workshops and classes occur the week leading up to the show.
Market – Vendors sell fabrics, quilting supplies and handcrafted goods.
Charity – Proceeds benefit the Sisters Outdoor Quilt Show and education programs.
Parking & shuttle – Free shuttle service from Sisters High School; parking within town is limited.
Tips – Arrive early to beat the heat and crowds; bring sunscreen and water.
Balloons Over Bend (Jul 24‑26, 2026)
Balloons Over Bend is a beloved summertime festival featuring colorful hot air balloon launches at dawn, Night Glow events and family activities. The festival typically takes place over three days at R.E. Jewell Elementary in Bend and at American Legion Park in Redmond.
Dates – July 24 – 26 2026 (per Lay It Out Events calendar)
Morning launches – Hot air balloons lift off at dawn each morning; spectators can arrive early to watch inflations and take photos
Night Glow – Evening events in Bend and Redmond feature tethered balloons glowing against the night sky, accompanied by live music, food carts and a beer garden
Family activities – A kids’ area offers bounce houses, games and crafts.
Market – Vendors sell handmade goods, art and festival merchandise.
Balloon Blast race – A short fun run for kids encourages them to race the balloons to the finish line.
Admission – Some events are free; others require tickets (e.g., Night Glow).
Accessibility – Parking and shuttle information is provided on the event site.
Weather – All balloon flights depend on favorable weather; check the festival site for updates.
Deschutes County Fair & Rodeo (Jul 29 – Aug 2, 2026)
The Deschutes County Fair & Rodeo is the largest county fair in Oregon and draws over 250,000 attendees each year. It blends traditional rodeo events with concerts, livestock exhibitions, carnival rides and fair food.
Dates & hours – July 29 (11 a.m.) through August 2 (8 p.m.) 2026
Location – 3800 SW Airport Way, Redmond, OR
Rodeo – Professional rodeo performances take place daily; events include bull riding, bronc riding, barrel racing and roping.
Concerts – National musical acts headline each evening.
Livestock & exhibits – Youth and open-class livestock shows, craft and baking competitions, horticulture displays and petting zoo.
Carnival – Full midway with rides, games and fair food.
Admission & passes – Single-day and multi-day passes available; rodeo tickets sold separately.
Parking – Large lots at the fairgrounds; early arrival recommended.
Fun fact – The fair is the largest annual event east of the Cascades
Reggae Rise Up Oregon (Jun 12 – 14, 2026)
Reggae Rise Up brings reggae legends and rising stars for three days at the Deschutes County Fair & Expo Center. The event includes camping and fosters a laid‑back festival atmosphere.
Dates & location – June 12 – 14 2026 at the Deschutes County Fair & Expo Center in Redmond
Lineup – Artists have not been announced for 2026, but previous years feature top reggae, roots and island‑inspired acts
Camping – Tent camping is available on-site; RV camping is generally not offered
All ages – The festival is open to all ages
Festival scene – Live art installations, food trucks, craft vendors and community workshops.
Tickets – Single-day and three-day passes; purchase through the official site
Getting there – Parking available at the fairgrounds; shuttle service may be offered from Bend.
Weather – Expect warm days and cool nights; pack accordingly.
Website – Additional information and lineup announcements will be posted on the festival site.
Haulin’ Aspen (Aug 8, 2026)
Haulin’ Aspen is a trail running race that offers a full marathon, half marathon and a 6.5‑mile race called the “Half As.” The course winds through ponderosa pines near Wanoga Sno-Park and features challenging climbs and rewarding views.
Date – August 8 2026
Distances – Marathon, half marathon and 6.5‑mile “Half As” trail race
Course – Single‑track trails with rolling hills, scenic meadows and mixed elevation gain
Amenities – Aid stations stocked with water and electrolytes; finishers receive medals and a commemorative item
Post‑race celebration – Festivities include a beer garden, live music and awards ceremony.
Location – Wanoga Sno‑Park, about 15 minutes west of Bend.
Registration – Early registration recommended; the marathon has a limited field to minimize trail impact.
Weather – Conditions can range from cool morning temperatures to warm afternoons; bring layers and sunscreen.
Charity – A portion of proceeds supports local trail maintenance and youth running programs.
Theater in the Park (Aug 14 – 15, 2026)
Presented by Lay It Out Events and the Tower Theatre, Theater in the Park brings professional theatre productions to an outdoor stage in Drake Park. Audiences sit on the lawn under the pines while watching Broadway-quality performances.
Dates – August 14 – 15 2026 (exact play and showtimes TBD)
Venue – Drake Park, Bend.
Past productions – Previous years have staged classics like Steel Magnolias and musical revues with professional actors and live bands.
Seating – Lawn seating; low-back chairs and blankets recommended.
Food & drink – Picnic baskets welcome; local food vendors and a beer/wine garden on-site.
Tickets – Purchase through the Tower Theatre or Lay It Out Events; shows often sell out.
Family friendly – Suitable for all ages, though some productions may include mature themes; check before bringing young children.
Proceeds – A portion of ticket sales benefits local arts education programs.
Rain plan – Performances continue rain or shine; umbrellas discouraged to preserve sightlines.
The Little Woody (Aug 28 – 29, 2026)
The Little Woody celebrates barrel-aged beer, ciders and whiskeys. The 2026 festival takes place on the grounds of the Deschutes Historical Museum in downtown Bend and will feature rare brews, special tastings and quirky competitions.
Dates – August 28 – 29 2026
Tasting lineup – Focuses on barrel-aged beers, ciders and small-batch whiskeys; breweries bring one-off specialties and cellared favorites
VIP experience – VIP ticket holders gain early entry, commemorative glassware and access to rare pours
Entertainment – Live music, a secret comedy show, the Bend Beer Run (see below), and the always popular Gnome in Your Home contest
Bend Beer Run – A fun 5 k race with beer stops along the course is part of the festival weekend
Merch & food – Festival merchandise including gnome hats and bottle openers; food trucks serve pub fare and sweets.
Age limit – 21+ only; ID required.
Tickets – General and VIP passes available; includes tasting tokens and a glass.
Location – Deschutes Historical Museum lawn, downtown Bend.
Bend Beer Run (Aug 29, 2026)
Part of The Little Woody weekend, the Bend Beer Run is a 5 k that pairs exercise with craft brews. Runners start at the Deschutes Historical Museum and stop at several breweries along the route.
Date & time – August 29 2026 with morning start times (exact time posted closer to the event)
Course – Starts and finishes at the Deschutes Historical Museum; runners stop at multiple breweries to sample craft beer
Registration – Includes race entry, Little Woody tasting glass, three tasting tokens and entry into the Little Woody festival
Costumes – Participants often wear gnome costumes or beer-themed outfits; prizes awarded for best costume
21 + only – Runners must be 21 or older; ID required at check-in.
After party – Runners can enjoy the Little Woody festival after the race and redeem tokens for more tastes.
Packet pickup – Occurs the day before at a local running shop.
Parking – Limited downtown parking; biking or carpooling encouraged.
Beneficiary – A portion of race proceeds supports local non‑profits.
Bend Comedy Festival (Sept 4 – 6, 2026)
The Bend Comedy Festival returns over Labor Day weekend with stand‑up shows, workshops and interactive events across multiple venues. Organized by the women- and queer-led Bend Comedy and Arts Foundation, the nonprofit festival celebrates community and creativity.
Dates & location – September 4 – 6 2026 in downtown Bend
Origins – The inaugural 2025 festival sold out many shows and featured over 20 events at venues like Midtown Ballroom and Volcanic Theatre Pub
Programming – Expect classic stand‑up showcases, nationally touring headliners, workshops, sketch comedy, musical comedy, a queer comic showcase and even comedic jazzercise
Passes – All‑access and VIP passes include entry to all shows plus exclusive merchandise and late‑night hangouts
Tickets – Early bird pass sales begin March 1 2026 with individual show tickets available later
Community – Focuses on uplifting fresh comedic voices and building community; profits support the Bend Comedy and Arts Foundation.
Venues – Shows hosted at multiple locations within downtown Bend; schedule released closer to summer.
Audience – 21+ recommended for evening shows; some daytime programs may be family friendly.
Volunteer – Opportunities available via the festival website.
Oktoberfest Bend (Sept 19, 2026)
Bend’s Oktoberfest is a single‑day celebration of Bavarian culture featuring craft beer, music and quirky competitions. The event takes over the Deschutes Historical Museum lawn and adjacent streets.
Date & time – Saturday, September 19 2026 from 2 p.m. to 9 p.m.
Beer & food – Local breweries pour Oktoberfest‑style lagers and German‑inspired beers; food vendors serve pretzels, brats and traditional Bavarian fare
Entertainment – Live music, yodeling and wiener dog races entertain the crowd
Games – Stein holding contests, pretzel toss, people-powered keg races and human tic‑tac‑toe add playful competition
Dog events – The Bark Bash dog races and costume contest invite pups to join the fun
Family activities – Kids’ zone with inflatables, crafts and face painting; all ages welcome.
Admission – Free entry; purchase tokens for beer and activities.
Proceeds – Benefits the nonprofit Lay It Out Events and various local charities.
What to wear – Traditional lederhosen and dirndls encouraged; prizes for best dressed.
Cascade Equinox Festival (Sept 18 – 20, 2026)
Held at the Deschutes County Fairgrounds in Redmond, the Cascade Equinox Festival blends jam bands, electronic music and funk with experiential art and community workshops. The 2026 edition is slated for September 18 – 20.
Dates & location – September 18 – 20 2026 at the Deschutes County Fair & Expo Center in Redmond
Music – Multi‑genre lineup featuring jam, electronic, funk, soul and bluegrass performers
Experiential programming – Vendor marketplace, diverse food options, Healing Sanctuary with yoga and workshops, interactive art installations, a Solar Spin roller rink and kids’ areas
Camping & lodging – On-site camping available; glamping options offered for an extra fee.
Workshops – Educational talks and sustainability initiatives; festival encourages leave‑no‑trace ethics.
Tickets – Multi‑day passes and VIP packages; early bird pricing available.
Family friendly – Kids under a certain age admitted free; dedicated family zones and activities.
Weather – Expect warm days and cool evenings; pack layers.
Note – Detailed lineup and schedule to be announced on the festival site later in 2025.
Sunriver Oktoberfest Race (Sept 26, 2026)
This 10 k and 5 k fun run takes place at Sunriver Village and includes free admission to the Oktoberfest celebration afterward. The race encourages participants to wear lederhosen and dirndls and rewards them with beer and swag at the finish.
Date & time – Saturday, September 26 2026
Distances – 10 k and 5 k courses on paved paths around Sunriver
Finish goodies – Race bib, professional timing, commemorative medal, T-shirt and entry into the Sunriver Oktoberfest
Beer & festival – Runners receive a beer ticket redeemable at the Oktoberfest beer tent
Family friendly – Kids fun run and costume contest; strollers welcome on the 5 k course.
Charity – Proceeds support Sunriver Women’s Club philanthropic programs.
Parking – Ample parking at The Village; arrive early.
Registration – Sign up online; prices increase closer to race day.
What to wear – Bavarian attire or festive fall costumes encouraged.
Sisters Folk Festival (Sept 25 – 27, 2026)
This renowned multi‑genre music festival transforms the town of Sisters into an intimate network of stages and listening rooms. The 2026 festival runs September 25 – 27 and features more than 30 performing artists across seven venues
Dates & venues – September 25 – 27 2026 in downtown Sisters
Stages – Seven stages include Sisters Art Works, Village Green, Oliver Lemon’s, FivePine Lodge and others
Artists – 30+ artists representing folk, Americana, blues and world music
Atmosphere – Intimate listening-room vibe; festival strives for artist and audience connection
Village Green venue – The community‑centered Village Green stage features craft vendors, food carts and beer/wine service
Camping & lodging – Weekend camping at Sisters High School and Shepherd of the Hills Church; dry camping only
Workshops – Songwriting, storytelling and instrument clinics offered throughout the weekend.
Passes – Three-day passes include access to all venues; single-day tickets available later.
Community – Produced by Sisters Folk Festival Inc., a nonprofit that supports music education and community arts.
Bend Fall Festival (Oct 2 – 4, 2026)
The Bend Fall Festival ushers in autumn with a downtown street fair featuring fine art, harvest markets, live music and family activities. According to its vendor application, the 2026 festival is scheduled for October 2 – 4zapplication.orgzapplication.org.
Dates & hours – October 2 – 4 2026; artist booths open Saturday 11 a.m.–8 p.m. and Sunday 11 a.m.–5 p.m.zapplication.org.
Art & craft – Six downtown blocks host vendors selling fine art, jewelry, ceramics, woodworking and textileszapplication.org.
Harvest market – Features locally grown produce, pumpkins and autumn treats.
Family fun – Kids Zone with pumpkin painting, carnival games and a petting zoo.
Music – Multiple stages with local and regional bands playing rock, blues and funk.
Libations – Beer, wine and cider gardens with seasonal brews; food carts offering fall flavors.
Admission – Free; tokens for drinks and activities sold on site.
Parking – Downtown lots fill quickly; bike valet or shuttle encouraged.
Proceeds – Supports Lay It Out Events’ community programs.
Bend Film Festival (Oct 7 – 11, 2026)
The BendFilm Festival celebrates independent cinema with screenings, panels and networking events across downtown Bend. The 23rd annual festival is confirmed for October 7 – 11 2026
Dates – October 7 – 11 2026
Focus – Competition program highlights new North American independent films; shorts programs include works from around the world
Venues – Screenings take place at venues such as Tower Theatre, Tin Pan Theater, Regal Old Mill IMAX and other downtown locations
Awards – Cash prizes for best narrative, documentary, environmental/outdoor and indigenous films; total awards exceed $9,350
Basecamp retreat – The festival offers a filmmaking retreat called BendFilm: Basecamp, focusing on emerging narrative and documentary filmmakers
Recognition – Named one of MovieMaker magazine’s “Top 25 Coolest Film Festivals in the World,” the festival screened 116 features and shorts in 2025 with 46% directed by women
Passes – Festival passes and individual tickets available; many events sell out.
Community – Includes filmmaker Q&As, industry panels, parties and networking events.
Volunteering – Opportunities for film lovers to support screenings and events.
Happy Girls Run – Sisters (Oct 24, 2026)
The Sisters edition of the Happy Girls race series offers a trail half marathon through the Deschutes National Forest and shorter road races in town. The event emphasizes camaraderie and scenic courses.
Date – October 24 2026
Distances – Trail half marathon plus 10 k and 5 k road races
Course – The half marathon follows dirt trails through ponderosa pines and meadows; the 5 k/10 k route winds through downtown Sisters and finishes at FivePine Lodge
Swag & awards – Finishers receive a medal or belt buckle, race shirt and other goodies
After party – Live music, beer, food and awards ceremony at Three Creeks Brewing or a local venue.
Community – Encouraging environment for women of all ages and abilities; many participants return each year.
Registration – Online sign‑up; early bird pricing and team discounts.
Charity – Supports programs for girls’ education and empowerment.
Packet pickup – Held the day before at a Sisters running store.
Sunriver Music Festival (Aug TBD, 2026)
Although specific dates have not been announced, the Sunriver Music Festival has confirmed that its 49th season will take place in August 2026. The festival presents classical concerts, pops performances and educational programs in venues throughout Sunriver and Bend.
Dates – August 2026 (exact dates TBD)
Programming – Orchestral concerts, chamber music, solo recitals and family-friendly pops performances.
Venues – Sunriver Resort, Bend’s Tower Theatre and outdoor locations.
Education – Includes a Young Artists Scholarship competition and music education programs
Membership – Friends of the Festival receive early ticket access, discounts and special events
Ticketing – Single-concert and season passes; membership suggested for priority seating.
History – Nearly five decades of concerts showcase regional and national performers.
Community – Nonprofit festival contributes to music education in Central Oregon.
Website – Check for updates on 2026 concert dates and artists.
FairWell Festival (TBD Summer 2026)
FairWell Festival is a country, folk and Americana festival held at the Deschutes County Fair & Expo Center. The 2026 dates have not been confirmed, but it is expected to return in July. Past festivals featured major headliners across multiple stages and camping on-site.
Projected dates – Official dates for 2026 are not yet announced; a July timeframe is expected
Music – More than 30 acts across three stages, spotlighting folk, blues, rock, country and soul
Venue – Deschutes County Fair & Expo Center in Redmond
Camping – Tent camping available; RV camping may not be offered
Family friendly – All ages welcome
Tickets – Sold as single-day or multi-day passes; check the festival site for updates
History – The 2025 festival cut to two days and featured artists like Tyler Childers and Sturgill Simpson
Organizers – Produced by C3 Presents and Live Nation; ensures top-tier production.
Awaiting announcement – The official website will post the 2026 lineup, camping details and ticket release dates.
Art in the High Desert (Dates TBD 2026)
Art in the High Desert is Central Oregon’s premier juried art show and has found a permanent home at Riverbend Park in Bend. While dates for 2026 have not been posted, the show traditionally occurs in late August.
Purpose – Run by artists for artists, the show aims to help artists sell their work and maintain high standards of originality
Quality – Consistently ranked among the top 25 selling art shows in the country; known for high-quality, original fine art and craft
Location – Riverbend Park along the Deschutes River in Bend offers scenic views, public parking, restrooms and picnic areas
Admission – Free to attend; artists must apply and be juried into the show.
Booth rules – Strict rules ensure only original art; no mass-produced goods or imports
Visitors – Many locals and tourists plan vacations around the show; there are usually over 100 artists.
Additional events – Live music and food trucks complement the art.
Date note – Check the show’s social media or website for the 2026 schedule (likely late August).
Contact – Applications and guidelines posted on the ZAPP application site
Additional Community Events
Several smaller community events also take place in 2026:
July 4 Pet Parade – A beloved Bend tradition since 1924, the parade invites residents to dress up with their pets and walk through downtown. Lineup begins at 8:30 a.m. and the parade starts at 9:30 a.m.; registration is not required and the route runs from Harmon Park to Drake Park
Tips for Pet Parade – Participants must leash and clean up after pets; no registration or candy distribution is allowed
Munch & Movies – An outdoor film series often accompanies Munch & Music in August; check local listings.
4 Peaks Music Festival – On hiatus; organizers hope to return after a break
Bite of Bend – The food festival has not announced 2026 plans after several years off.
Bend Design – A fall conference exploring creative thinking may return in 2026.
Festivals that passed in 2025
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/
Check out places to eat, drink & stay for the festival!
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
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.
