This is top-secret, okay? I love September more than any other month in Bend. 

Don’t tell the other months, but nothing compares to September’s glorious blend of sunny days, cool nights, casual vibe, and quieter trails. 

While each month’s magical in its own way, here’s what’s amazing about September in Bend, Oregon.

There are 7 territories of breweries to discover along the Bend Ale Trail.

Summer’s sweet encore

Here’s the truth: 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. 

Stick to the trails and practice the Bend specific Leave No Trace principles.

September’s best hikes

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, Cultus 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.

Downtown Bend offers a variety of shops and boutiques—you are sure to find something for everyone on your list.

Shop for fall

Raise your hand if you live for end-of-season sales! 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. 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.

There are a few shows left in the Hayden Homes Amphitheater summer lineup.

Savor some live music

Now that you’re stocked up on layers, tie 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.

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 Flights Wine Bar, Faith, Hope, and Charity, 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.

Challenge yourself with the bouldering routes at Circuit Bouldering Gym.

Spend some time indoors

The only thing I don’t love about September in Bend is when wildfire smoke drives us all inside, thanks to hazardous air quality floating through our fair town. It seldom lasts long, but it’s handy to have a few indoorsy plans in your back pocket.

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 you’re more into house cats than wild ones, swing by Playful Paws Cat Cafe for some sweet whiskered kisses.

To get the kids’ wiggles out, bounce around at Trampoline Zone or Mountain Air. If vintage video games are your jam, Vector Volcano is the spot to be.

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. 

From bowling alleys to bumper cars to indoor kart racing, to indoor climbing gyms there’s tons of fun stuff to do indoors when you’re in Bend.

For more ideas on indoorsy fun in Bend, check out this post.

Score an epic sunset pic

September’s gusts of wildfire smoke do come with one small plus. That’s the jaw-dropping sunsets painting the sky with vivid pinks, oranges, and purples, or the vibrant sunrises stirring you awake with more colors than a Crayola box. Red alert: Have your camera handy at all times!

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? 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. 

Wanderlust offers guided tours for a variety of outdoor activities in the area.

Can we still splash around?

With summertime crowds gone, you’ll score your own private lakefront trail when you head for the Cascade Lakes most weekdays. Even on weekends, things are quieter when you head out 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—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 Lady Bird, 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!