6 things to do in Bend, Oregon in the fall + where to stay in Bend

In October, Hubs and I celebrated our wedding anniversary. As much as we travel, we nearly never get away just the two of us. So we decided to make a super-special trip to reconnect and rekindle our love exactly 11 years after we said “I do.” So we headed to Bend, Oregon—one of my favorite spots in Oregon in the fall.

After all, fall in Bend, Oregon is this Central Oregon city’s shoulder season. Most people visit Bend in the summer for all its outdoor fun or in the winter for snow sports. But I can’t get enough of all the things to do in Bend, Oregon in the fall.

After all, most of the crowds clear out once the school year starts. The weather turns mild and absolutely gorgeous: think cold mornings, sunny days and close to zero rain. Finally, many hotels in Bend and other businesses offer discounted rates in the fall, since the number of visitors drops during this season.

In fact, our friends at Pine Ridge Inn invited us to stay in one of their suites for our anniversary weekend. This lovely boutique hotel in Bend has a front-row view to Bend’s fall colors, and our suite overlooked the Deschutes River from atop the canyon that runs through town. The Pine Ridge Inn served as our starting point for all the fun things to do in Bend, Oregon in the fall.

To read about all the best things to do in Bend and where to stay in between your adventures, keep reading. And don’t forget to pin this post for later, when you’re planning your own trip to Bend, Oregon!

1. Hike Tumalo Falls in Bend, Oregon

Tumalo Falls is one of the busiest spots in Bend, Oregon to explore the outdoors—but this fairly easy hike is way less crowded in the fall.

Just a half-hour drive from Downtown Bend, Tumalo Falls drops nearly 100 feet from a pine tree-covered bluff. After you park in the (admittedly tight) parking area, you walk just a few minutes to see Tumalo Falls. (Just make sure to pay the day pass parking fee. In fact, we bought our pass at our hotel in Bend, Pine Ridge Inn, which was *such* a convenient and thoughtful perk!)

From Tumalo Falls, you can hike for miles through the Deschutes National Forest. Hubs and I hiked about 1.25 miles past Tumalo Falls to Middle Tumalo Falls, a two-parter waterfall where we saw pretty much no one else.

Middle Tumalo Falls is a great turnaround spot if you have plans for lots more things to do in Bend. The trail is also moderately easy. Maxine and Edie, ages 4 and 6, would have a fine time hiking this trail in Bend.

2. Feel like a local at Bend’s Fall Festival

Hubs and I were lucky enough to visit Bend, Oregon during its annual Fall Festival, which takes place at the beginning of every October. This weekend-long event takes over Downtown Bend, closing streets to make room for live music, food carts, local artisans and breweries.

I joke that Bend is pretty much obsessed with street fairs because one is happening almost every time we’ve visited this Central Oregon city. Tons of people turn out for these outdoor fests—and the Fall Festival should be on your list of things to do in Bend in the fall!

3. Get a lay of the land on Pilot Butte

Central Oregon is basically one big volcano. Pilot Butte in Bend, Oregon was formed when debris from a volcanic eruption fell to the ground and cooled, leaving a flat-topped mound from which you can see all of the city.

Several hiking trails wind around the butte, but we drove up to the top. From Pilot Butte, you can see the mountains surrounding Bend—Mt. Bachelor, Sisters, Three-Fingered Jack and more. We could even see our own home mountain, Mt. Hood, since the fall day was so clear!

Pilot Butte tends to be one of the top things to do locals recommend to folks visiting Bend. It’s a terrific way to get a sense of Bend’s layout and take in the wide vistas around the city.

4. Take in the fall colors in Drake Park

One of my favorite places to visit in Bend, Oregon in the fall is Drake Park. Hubs and I walked beneath all the fall foliage and along the park’s half-mile of trails along the Deschutes River.

It’s hard to get more beautiful than the colorful trees reflected in the park’s Mirror Pond. (Yep, that now-famed Mirror Pond from Deschutes Brewery!)

What’s more, my favorite stretch of Drake Park is just a few blocks from Downtown Bend’s main corridor. If you fancy a quick shopping stop, I love buying postcards, mugs, ornaments and other gifts made by local designers and artists at The Bend Store, about a 2-minute walk from Drake Park.

5. See the stars on a nighttime canoe trip

Hubs and I wanted to make our anniversary trip to Bend, Oregon extra-special. So when Bend-based Wanderlust Tours offered to host us on a nighttime canoe tour, we jumped at the chance.

Wanderlust Tours offers a variety of outdoor experiences, from kayaking trips to photography tours. They all sound fun, but canoeing by moonlight—pretty sure that can’t be beat.

Wanderlust Tours picked us up and drove a group of up Mt. Bachelor to Hosmer Lake. Before we got on the water, our tour guide Courtney gave us a quick tutorial on how to work together to paddle and steer. Hubs and I were the first ones to push our canoe out into the pitch-black water.

We followed Courtney as she led us past reeds and through the winding channels of this high-alpine lake. Above us, the half-full moon shone and stars twinkled. I spent my childhood on the water, whitewater kayaking all summer, but I’d never paddled in the middle of the night before.

One of the most magical moments of our entire trip to Bend this fall was when our entire group paused in the middle of Hosmer Lake. We were all quiet, listening to the nighttime world around us. The occasional drip of water or frog croak were the only sounds that broke the silence.

In our busy lives, it’s rare to be wholly immersed in nature like this. We will definitely be back to explore other parts of Bend with Wanderlust Tours.

6. Feel (really) small at Smith Rock

If you haven’t gathered this year, Bend, Oregon is a wonderful place to dive into the outdoors—especially in the fall. And one of the most stunning parts of this Central Oregon landscape is just a short drive from Bend at Smith Rock.

Around 30 million years ago, the area that is now Smith Rock State Park collapsed into a caldera of molten rock. (Cool, right?) Then that caldera filled with ash, debris and more rock when nearby volcanoes erupted. All that debris hardened together, forming the spires and cliff faces that make Smith Rock so imposing.

All these millenia later, Smith Rock makes an unforgettable day trip from Bend, Oregon. Its trail system is like a choose your own adventure story: You can climb up to the cheerfully named Misery Ridge, on the flat paths along the river, or in any of the other 10 official hiking trails.

Make sure to pay the $5 day use fee (or use your annual Oregon State Parks Pass, which we have and use just about every week). And know that dogs are welcome in the park as long as they’re on-leash. Just make sure to bring water for yourself and your pup, as hiking here is thirsty work, even in the fall.

Autumnal hotels in Bend, Oregon

When we celebrated our anniversary in Bend, our friends at the Pine Ridge Inn hosted us for two complementary nights in a Canyon View Suite—they really know how to make an old married couple feel special! And this small, boutique hotel in Bend felt like a prime spot to experience fall in Central Oregon. I mean, just look at these colors!

Hubs and I spent so much time in front of the suite’s gas fireplace, getting cozy in between all our adventures in Bend. And you better believe I drank my tea every morning on the suite’s private patio.

We also couldn’t get enough of our view overlooking the Deschutes River.

One of the things that made the Pine Ridge Inn feel so perfect for our special getaway was how intimate the hotel is. With only 20 rooms in the entire property, we felt so well taken care of. The people working the front desk knew us by name and chatted whenever we came or went, and they got to know us a bit. That way their recommendations of what to do and where to eat in Bend were spot-on! (I’m still thankful they tactfully steered us away from a sub-par restaurant where we were going to eat out of convenience and recommended the delicious 10 Barrel West Bend pub instead.)

From when we first arrived (and were greeted with a complimentary glass of wine and craft beer) until our final morning (when we noshed locally made granola and other breakfast goodies in the complimentary breakfast bar), we felt welcomed and pampered at Pine Ridge Inn.

Already missing Bend, Oregon

As Hubs and I left Bend, Oregon in our rearview mirror, we talked about how much we love this Central Oregon town. One of my favorite things about Bend is how sunny it is year-round, including in the fall. And since I suffer from SAD during the winter months, we talked about coming back to Bend several more times this fall and winter.

With weeks and months of rainy, grey weather coming up, I feel so much better knowing we have a sunny destination just a few hours’ drive from Portland.

Bend turned out to be the ideal spot for Hubs and me to celebrate our anniversary. After all, everything we’ve done together—move across the country several times, support each other through graduate school, adopt a rescue dog, raise two incredible humans, and continue to love each other’s faces off throughout it all—deserves a little celebration.

No, nix that. It deserves a lot of celebration.

So cheers to us!