What’s the best time of year to visit Bend? 

Give me five cents for each time I’ve answered that question in 27 years of living here, and I’d have 8,000 nickels to spend on fresh hop beer, concert tickets, farm-to-table dining, and everything else that makes September Bend’s best. 

That’s my two cents, anyway.

While each month’s magical in its own way, here’s what I think makes September the best month in Bend, Oregon.

It’s still summer, but better

I’m not gonna lie, summer gets busy in Bend. It hits a peak on Labor Day weekend when everyone flocks here for kayaking, camping, floating the river, and one last outdoor concert before summer comes to a close.

But those who know Bend best smile a little bit smugly at that. Why? Because all of those things are even better in September. 

Those rental float tubes you fought for in August? We’ve got plenty to share after Labor Day. The restaurant reservations you struggled to nab in July? I see plenty of tables now. Fans of live music (*raises both hands*) know Hayden Homes Amphitheater likes to go out with a bang, with so many shows in September. 

Want to try mountain biking? Hit the trails with Cog Wild once the summer crowds die down and learn why Bend’s been named to so many best-of lists. It’s a great time to learn at a quieter pace when temps are just perfect.

And Bend Ale Trail fans know that fresh hop season is reason enough to hit Bend in September. Need another? Grab our new Fresh Hop Bingo card that lets you earn a cool prize for sipping your way around breweries this season. Pick up yours at the Bend Visitor Center for zero pennies and get ready to have your hoppy mind blown.

Lace up your boots and hit the trail

Once peak summer season slips past, Bend’s best hiking trails get way less crowded. But the best news is that the weather’s still warm, and three months of summer wiped snow off most high-elevation trails. 

Make a midweek loop on the 7.8-mile trail around Paulina Lake and you’ll hardly see another soul. Spots like Tumalo Mountain, Todd Lake, Lucky Lake, Blow Lake, Cultus Lake, and the Six Lakes Trailhead are especially awesome this time of year.

As temps cool near the end of the month, it’s a good time to try trails you skipped during peak summer heat (lookin’ at you, Oregon Badlands Wilderness).

While a Cascade Wilderness Permit remains required for many popular trails through mid-October, they’re easier to snag this time of year than when you tried back in July. If you’re dreaming of Green Lakes or Tam MacArthur, give it a shot scoring a permit in September.

Starting September 15, your dog gets a bit more freedom when leash requirements drop on the Deschutes River Trail between Benham Falls and Meadow Camp. Ditto that for trails in the Three Sisters Wilderness between the South Sisters climber’s trail and Todd Lake. Just be sure to pick up after Fido, and keep him contained if he’s prone to chasing wildlife or other hikers. 
It’s also smart to keep an eye on wildfire activity to be sure you’re not stumbling into something sketchy.

Did someone say sale?

Nothing beats end-of-season sales, especially in a town where shops discount summer gear while we’ve still got 4-6 weeks of great temps. Try your hand at Bend’s seasonal sales to score the best deals on summer attire and outdoor gear like kayaks and tents. 

Scope out Bend’s abundant shopping options, from the shops in the Old Mill District to the boutiques in historic Downtown Bend to other zones like the Box Factory, Bend Factory Stores, and Cascade Village Shopping Center.

Bend weather in September calls for extra layers, so watch for things like sweatshirts and cute beanies to keep you toasty on cool evenings. Layering’s key for chilly mornings in particular. From warm hiking socks to a funky thrift store flannel shirt, your wearable souvenirs can do double duty keeping you warm and reminding you of your epic Bend adventure.

Rock right into fall

Once you’ve shopped for layers, cinch that new fleece around your waist and head for one of Central Oregon’s awesome outdoor concert venues.

The Hayden Homes Amphitheater still has several shows on the docket in September. Earlier sunsets mean less time spent squinting and fanning yourself in the hot sun. Pay attention to the start time on your ticket, since shows tend to start earlier as the sun sinks sooner. I also suggest biting the bullet and paying twelve bucks to rent one of their chairs, which gets your backside up off the cold, damp grass.

For a special musical treat, head west for the time-honored tradition of the Sisters Folk Festival. It’s a multi-day event featuring a celebration of acoustic music, cultural arts, and some of the biggest names in folk and bluegrass.

Other spots worth checking for live music this time of year: Flights Wine Bar, Oregon Spirit Distillers, The Grove, and Suttle Lake Lodge, where you’ll enjoy stellar views and great tunes. Scope out Visit Bend’s event calendar to see what’s happening while you’re here.

Gulp that good clean air

The unpredictable nature of wildfire means you never know when poor air quality might drive you indoors. Lucky for you, there’s plenty of fun indoorsy play in Bend.

Plan a fun family outing at the High Desert Museum where both indoor and outdoor exhibits brim with native wildlife, indigenous art, interactive exhibits, and natural history. 

Book a date night at one of Bend’s award-winning restaurants and prepare to be wowed by harvest-fresh food this time of year.

If the kids get squirrely, head for Trampoline Zone or Mountain Air for a few hours of bouncing. Older kids will dig Bend’s abundance of indoor climbing gyms, or hit Vector Volcano for some fun with vintage video games.

Feeling artsy? Book a class at Freak’n Art and pick from options like So Sketchy (charcoal and conte crayon drawing) or Just Add Water (watercolor pencil drawing/painting). You can also try DIY Cave for classes like welding or jewelry-making. Once you’re done,l take home a one-of-a-kind souvenir that you made yourself.

Missing your feline friends back home? Stop by Playful Paws Cat Cafe for a vacation kitty fix and a shot at finding an adoptable buddy. 
From bowling alleys to bumper cars to indoor kart racing, I promise you’ll love Bend’s indoor spaces. For more ideas on making backup plans in Bend when weather won’t cooperate, check out this article.

September sunsets galore!

If we do get smoke in September, there’s a great silver lining in those clouds. Actually, make that a pink and red and orange and magenta lining, in the form of the best sunsets of the year. 

For epic views from above, try catching a sunrise or sunset from atop Tumalo Mountain or Lava Butte between Bend and Sunriver. 

Another great pick closer to town is Pilot Butte, which comes with the bonus of having both a hiking trail and a drivable road to the top. That’s a great spot for both sunrise and sunset, but pack a headlamp for the hike down if you opt for the latter.

You’ve undoubtedly seen photos of Bend’s iconic Mirror Pond, so why not snap your own? Sunsets and sunrises are both pretty great from this spot, so head to Drake Park with a cup of coffee and your camera and prepare to capture the ultimate souvenir.

Take me to the lake…

Now that summer crowds have moved on, score your own private lakefront trail when you head up the Cascade Lakes Scenic Byway most weekdays. 

Even on weekends, things are quieter on Bend’s lakes and rivers with a kayak or standup paddleboard. Wanderlust Tours offers daytime and moonlight canoe trips, so leave the gear and the driving to someone else and prepare for a once-in-a-lifetime adventure.

While the river shuttle stops running after Labor Day, you can still float the river if you’re willing to walk or do the double-car shuffle. Just be careful about parking near Drake Park, since tickets get expensive! 

With sunset coming earlier in September, it’s the perfect time for an evening paddle on the Deschutes River. Afterward, head to the Old Mill District for dinner at Lady Bird, Mill Works Pub, Greg’s Grill, or Anthony’s. If dinner’s not in the cards, just grab a glass of wine at Va Piano or Evoke.

Cheers to another amazing summer in Bend!