Cyclist amid fall colors in Bend, Oregon

The Definitive Guide to Fall Events in Bend, 2018

Bend, like a lot of places in the mountains, has two distinct personalities.

There’s summer Bend, with floats down the Deschutes River, festivals, beer, glorious sun, hiking, rock climbing, more beer, et cetera. Then there’s winter Bend, when the siren’s song of fresh powder at Mount Bachelor often proves irresistable.

Throughout the year, there’s a common denominator: Bend’s natural beauty shines forth regardless of the season. We mean that figuratively and literally, with sunny skies year round. Then, there’s always beer, locally brewed and delicious.

When it comes to Bend events though, don’t overlook the Fall. There’s a lot going on. So much, in fact, that trying to wade through all of it and plan your calendar might prove a big chore.

Luckily, though, we’ve done the hard work for you, finding the best of the best that the Bend area has to offer for September, October, and November. You’ll never look at fall the same again.

Psst: if you’re perhaps thinking of moving to Bend, we’ve got you covered there too. Just let us know what you’re looking for and we’ll help you get started on your home search right away.

Our business is real estate, but we’re passionate about our local communities. We want to do what we can to share that zest. So without further ado, here’s Bend’s top events for Fall 2018.

(Not yet ready for the summer to end? Then check out our Summer Events Guide.)

Sisters Folk Festival — September 7-9

There’s something about folk music that just feels right at higher elevations, particularly as the dog days of summer start to give way to crisp fall and its hints of bittersweet nostalgia. That’s just what you’ll get at the Sisters Folk Festival, just a short drive west of Bend.

Justin Townes Earle, Dar Williams, and Robbie Fulks headline, but the lineup is as deep as they get, with 48 diverse acts. And with 11 different stages, expect performances to be much more intimate than your average festival.

Here, the word “folk” describes something of a shared spirit rather than denoting strict genre boundaries. So, you can expect bluegrass, country, jazz, funk, afro-cuban, gospel, gypsy, swing, and more.

Wildfires in the Three Sisters Area made 2017’s festival a no-go, but cross your fingers for better conditions this year. So far, so good. Tickets are available here.

Bend Bicycle Film Festival — September 7
Wild & Scenic Film Festival — October 5
BendFilm Festival — October 11-14

It’s true that for many of Bend’s diehard outdoorsfolk, there’s no such thing as a winter vacation. But for many, summer’s outdoor pleasures steadily give way to indoor ones as the days and nights begin to cool.

That’s where these three film festivals come in. The first two feature films about, well, the outdoors, both of them screening at Old Bend’s historic Tower Theater. The Bend Bicycle Film Festival features short films by exclusively local filmmakers. The Wild & Scenic Film Festival, screened across the country, will benefit the Oregon Natural Desert Association. Expect nature, adventure, and environmental advocacy.

This year, BendFilm celebrates its 15th anniversary. A “celebration of independent cinema,” this is a can’t-miss event if you want to peer into the rich ecosystem of films being made today outside of mainstream Hollywood.

Flagline 50k — September 15
Hood to Coast High Desert — October 6
LaPine Loop — October 20

Bend, we’ll repeat, has more than its fair share of diehard outdoorsfolk and extreme athletes, from mountain bikers, runners, and climbers to kayakers and snowboarders. So no Bend events list would be complete without a sampling of some of the area’s adrenaline-pumping athletic competitions.

The Flagline 50k starts and finishes at Mt. Bachelor’s West Village Lodge. In between, expect a lot of climbing–4,000 feet of it, to be specific. For those not ready to tackle the 50k, 10k and 5k races are available.

Hood to Coast High Desert is an offshoot of the renowned Hood & Portland to Coast relay, long known as the “Mother of All Relays” and the longest in the world. This one is 70 miles long, spanning from Brasada Ranch northeast of Bend then down Highway 27 and back. If you ask us, that’s plenty long enough. Teams of 4-6 members compete over 12 legs.

The Lapine Loop is an innovative “adventure” race featuring mountain biking, trail running, paddling and, we’re told, perhaps a rope challenge. Beginners are welcome, and for those more seasoned a “Pro” Loop is available as well.

Bend Oktoberfest — September 21-22

When it comes to Bend events, there’s never too long to wait before beer takes front and center. Bend, naturally, has its own Oktoberfest–with the highest per-capita of microbreweries in the country, who could be surprised?

This Oktoberfest isn’t in October though–Bend’s residents apparently can’t quite wait that long after summer’s beer festivals come to a close. We’re not complaining though.

Bend’s breweries, naturally, will be showing their stuff, but expect local wine, cider and kombucha on tap as well. What’s more, there are going to be plenty of weiners–weiner dogs, that is. Downtown Bend will be going to the Daschunds, with various races and competitions.

Want to know what’s even sweeter? Admission is totally free. And, what’s more, the event is a fundraiser to help keep downtown Bend beautiful. Give back to your community, and let it give back its bounty to you, in the form of delicious local brews and food.

Sisters Fresh Hop Festival — September 29

Oktoberfest leave you thirsty for more? Then head just west of Bend to Sisters for this extravaganza of exclusively fresh-hopped beers from across Oregon.

To qualify as “fresh-hopped,” the hops have to be picked and then brewed within a 24 hour window. Hops are harvested in the early Fall, predominantly in the Pacific Northwest. So this, in other words, is your prime chance to enjoy the world’s freshest beer.

As if that weren’t enough of an enticement, consider: Glen Watkins, Leadbetter Band, and other acts TBA will soundtrack the event. Mark your calendars. More info here.

Bend Fall Festival — October 5-7

The Fall Festival is, as the name implies, the quintessential celebration of the season, and of all the things that make Bend great. Expect local food, art, crafts, music, and libations in the form of a harvest market, gourmet food and wine street, and two stages.

Even with all of this, you may be thinking that there’s still something missing from the picture. Actually, you’re right: we haven’t mentioned the annual pie baking and pumpkin carving contest or chili cookoff. There’s a Family Fun street for the kids as well. Make no excuses: this is where you’ll want to be the first weekend of October.

Haunted Illusions and Halloween Party with David Caserta — October 31

Perfect for Halloween, this evening’s proceedings will feature “tons of tricks and more than a few treats.” David Caserta is one of America’s most renowned illusionists, and we think the Tower Theater is a perfect venue: old, perhaps spooky, and definitely magical. Get your tickets before they disappear into thin air.

Cyclocross Crusade — November 3-4

In years past, the Bend leg of the Cyclocross Crusade coincided with Halloween, making for a delirious spectacle as scores of costumed, mud-splattered cyclists blasted their way through town. Unfortunately, the event will be several days later this year. But we won’t be surprised if some folks show up in costume anyway.

Costumes aside, this is definitely a high intensity athletic competition. But cyclocross isn’t just another bike race. The action unfolds over many laps on a short, circular course with both pavement and cross-country sections. Frequent obstacles mean that cyclists must continuously dismount and carry their bikes. So whether you plan to participate or not, it’s going to be a heck of a show.

Serious Crusaders will probably want to invest in a specially-designed cyclocross bike, but clunkers are welcome too. There’s even a special race for single-speed bikes, so there’s no excuse not to throw yourself into the ring. You may just feel the spirit of Bend enter into you.