Can I share a secret? Don’t tell the other months, but September’s my favorite in Bend. What’s not to love? The weather’s still warm and clear, but nights cool off enough to be refreshing. Crowds are smaller and more chill, but you’ll still find all your favorite outdoor activities.
Want the scoop on what’s best to see, do, and savor in September in Bend, Oregon? Read on!
One last hurrah!
I won’t lie: Labor Day weekend gets busy in Bend. You’re smart to plan early for tours, hotels, restaurant reservations, and other fun activities.
If you haven’t done it yet and you still hope to visit, don’t panic! Check hotel websites and tour operator schedules for cancellations, and pack an extra dose of patience. Wait times might be longer on a holiday weekend at your favorite Bend Ale Trail stop, but that just means more leisure time for savoring a pint and a sunset while you wait.
When planning your outdoor adventures, opt for lesser-known trails (try the Newberry National Volcanic Monument) and windows of time when crowds aren’t as big (think early morning or late afternoon). Have several backup plans so if you arrive to find a parking lot full, you can mosey on down to the next trail on your list without feeling bummed.
Where should we hike?
Once Labor Day slips past, Bend’s trails get a whole lot less crowded. Even better? The weather’s still warm and summer sun has wiped most snow off the 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, and the Six Lakes Trailhead are especially awesome this time of year.
While a Cascade Wilderness Permit remains required for many popular trails through October 15, they’re easier to snag this time of year than when you tried back in July.
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.
Shop for fall
I can’t be the only one who lives for end-of-season sales, right? Now’s the time to stockpile everything from discounted summer attire to outdoor gear like kayaks and tents.
Bend offers 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.
Since September’s when Bend weather calls for extra layers, watch for things like sweatshirts and cute beanies to keep you toasty on cool evenings. 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.
Shake your hips at an outdoor concert
Now that you’re stocked up on layers, tie that new fleece around your waist and head for one of Bend’s awesome outdoor concert venues.
The Clear Summer Nights concert series is still going strong in September with live music in an intimate spot among the trees. Grab a tasty meal from one of the food carts and lounge on the grass with a bottle of wine and great tunes.
You can also head for the Hayden Homes Amphitheater to enjoy one of the season’s remaining shows. They’ve still got tons of concerts the docket for September, and earlier sunsets mean less time spent squinting and fanning yourself in the hot sun.
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 great venues include Oregon Spirit Distillers, The Grove, and Suttle Lake Lodge, where you’ll enjoy plenty of fresh air and great tunes. Scope out Visit Bend’s event calendar to see what’s happening while you’re here.
Have an indoorsy backup plan
A reality of high desert life in late-summer and early-fall is that smoke from nearby forest fires might blow through at any time, making it less-than-awesome to play outdoors.
September’s when you want some indoor fun on your bucket list so you won’t miss a beat when it’s time to head inside.
Make dinner reservations at one of Bend’s award-winning restaurants. Plan a fun family outing at the High Desert Museum and enjoy both indoor and outdoor spaces with native wildlife, indigenous art, interactive exhibits, and natural history.
If the arts are more your scene, Bend boasts plenty of art galleries for indoor browsing. You can even catch a show at the historic Tower Theatre, or snuggle up with a beer and a basket of tots in the theater at McMenamins Old St. Francis School.
Snag a sunset pic
There’s an upside to that wildfire smoke I mentioned, and it comes in the form of jaw-dropping skies. Vivid pinks, oranges, and purples paint the sky when the sun wakes up or goes to sleep, so it’s smart to have your camera handy.
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? It’s a great spot for both sunrise and sunset, so head to Drake Park with a cup of coffee and your camera and prepare to capture the ultimate souvenir.
What about water?
Minus summertime crowds, you’ll find ample alone time on the Cascade Lakes when September rolls around. Head out on your own with a kayak or standup paddleboard, or go with a guide when you book a moonlight canoe outing with Wanderlust Tours.
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–tickets get expensive! Go here to learn more about tube rentals and where to put in and take out.
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 Boxwood Kitchen, Greg’s Grill, or Anthony’s, or just grab a glass of wine at Va Piano or Evoke.
Cheers to another amazing summer in Bend!