For the 50+ Traveler

The drive across Oregon from Portland to Bend is one of my favorites. There are two ways to do it: Take the interstate south and then head east on Highway 22, or just take U.S. 26 nearly the entire way. I recommend taking U.S. 26. You’ll truly drive through every Oregon climate.

Here’s what the drive was like the last time I did it: I left Portland in the morning and it was foggy and rainy (what else?). Once on Highway 26, I began to climb and climb (you’re climbing Mount Hood), and by the time I stopped for gas in Government Camp, it felt like it had dropped 25 degrees (“It’s not going to snow, is it?” I asked my wife). Then, with Mount Hood in my rearview, the drive quickly transitioned from deep forest to high plains. Around Warm Springs, you descend into this canyon, and you feel like you’ve somehow driven to Utah. And then from Warm Springs to Bend, you’re pretty sure you’re in the Arizona desert (but without the oppressive heat). Four climates in three hours. And that’s just the trip to get to Bend. Once there ...

Things To Do In Bend, Oregon

Bend is in Central Oregon -- almost smack dab in the middle of the state. Many people are familiar with the Portland area as well as the Columbia River Gorge and the Oregon coast. But Bend provides an altogether unique Oregon experience. You’re in the high desert, right next to the mountains. And that provides so much to do.

The Deschutes Brewery Tasting Room in Bend, Oregon.

Visit The Breweries

In the last 10 to 15 years, Bend, Oregon has become synonymous with craft beer. It’s often a “beer trip” destination, just like heading to Napa Valley to sample wines. One of the original craft breweries in the United States, Deschutes Brewery, is the reason for Bend’s beer scene, but there are so many other breweries in town that it would be difficult to try them all in one trip. Here are a few highlights:

  • Start with the Deschutes Brewery Tasting Room. Deschutes has been around since 1988 and this tasting room has been a must-visit destination for beer lovers for several decades.
  • Also try Boneyard Beer (it’s in an old auto-body shop) or Bend Brewing Company (try to sit right on the lawn in the back overlooking the river).
Mount Bachelor in Bend, Oregon.

Check Out Mount Bachelor

If your visit is during the winter, then this is a no-brainer for anyone who skis: Hit the ski slopes at Mount Bachelor. But even if you’re not a skier, or if you’re there in the summer, then a trip out to Mount Bachelor is still a must.

I still remember learning about the name when visiting Bend with my family when I was a teenager. Just to the north are three mountain peaks known as the Three Sisters. The single mountain peak to the south was known as Mount Bachelor.

One great way to enjoy Mount Bachelor and the surrounding area is to take the Cascade Lakes Scenic Byway. There’s nothing like a clear blue mountain lake, and there are at least 10 of them along this scenic loop. My favorite when I took the drive: Elk Lake.

Downtown Bend, Oregon.

Walk Around Downtown

Downtown Bend is a treat. It’s not just one Main Street; it’s several blocks of sidewalk cafes, bookstores, and clothing shops. There are dozens of restaurants here, so if you’re hungry, there will be many places to eat (more on that in a bit).

On a busy day, you might find parking difficult (there’s angled parking along all the streets, but the spaces fill quickly). If that’s the case, park in the public parking lot on Franklin Avenue right next to the river. That way, after you’ve finished your shopping or your fabulous meal, you can walk the trail along the river in Drake Park and then return to your car at the east corner of the park.

Kayakers on the Deschutes River.

Get Out On The Deschutes River

I’ve mentioned “the river” several times, but I haven’t talked about what it is. The Deschutes River runs right through downtown Bend. It’s a mountain river that I know very well. On a trip there with my family when I was a teenager, my first-ever whitewater rafting trip was on the Deschutes (between Bend and Mount Bachelor). At the end of the trip, my dad bought me a t-shirt that said: “I shot the Deschutes,” and I wore it until it had holes in it.

But “getting out on the river” doesn’t have to mean whitewater rafting. That can be fun, and there are several outfitters in the area who will take you on whatever kind of rafting trip you want, but it could also mean renting a kayak or paddleboard and exploring the calm part of the river near the city. There are several places to rent kayaks and paddleboards right downtown. The river is “calmed” in this area with a dam at one end, so this portion of the Deschutes is known as Mirror Pond.

Or, if you’re feeling really adventurous, take some whitewater kayak lessons and maybe even try the man-made Bend Whitewater Park with slow, medium, and fast rapids. Get there at the right time of day, and you might see someone with a surfboard “surfing” one of the man-made waves within the rapids.

A Bend Photo Tour.

Take A Photo Tour

This is another great way to explore the Bend area. You don’t even have to be a photographer with a fancy camera. There’s so much natural beauty in the area, and this is a great way to map it all out.

There are several ways to do this. One is to take a guided photo tour. Bend Photo Tours offers several guided tours in and around Bend. They know the best spots to get the best photos, so let them take you there. They also have self-guided photo tours if you prefer that. Either way, you have a guide to the best photos in the area, day or night.

Tumalo Falls in Bend, Oregon.

Go See Tumalo Falls

This can be a short adventure or a long adventure, but either way, you need to see Tumalo Falls when you’re in the Bend area. Located 13 miles from Bend, this can be a quick trip to the trailhead to get a photo of the falls or a day-long seven-mile hike to see all of the waterfalls in the area.

The place to start is the trailhead. The parking lot is very close to Tumalo Falls, so if you’re just going up there to see the falls and then head back to Bend, it’s a very simple walk from the parking lot. Bring your camera because you’ll want many pictures.

If you want to spend more time in the area, keep going on the Tumalo Falls Loop -- it doesn’t end at the falls. In fact, there’s a seven-mile trail you can take which will take you to several other waterfalls in the area. It can be enjoyed as an out-and-back trail, so just choose the length you want to hike and turn around halfway.

Breakfast from McKay Cottage Restaurant.

Best Restaurants In Bend

Bend has been growing exponentially in the last 20 years. Just in the last 10 years, inside the city limits (not counting outlying areas), the population has jumped from 76,000 residents to nearly 100,000 residents. With a population growing that quickly, new restaurants open almost weekly. Here are three great ones to try.

McKay Cottage Restaurant

This is your spot for breakfast. What’s better than a breakfast place with a bakery attached? Try to sit outside. Their outdoor seating in the morning is just about perfect.

And the food at McKay Cottage is even better. Their website boasts that they’ve been voted the best breakfast in Bend every year since 2010, so get there early so you don’t have to wait in line. And order something that includes a bakery item -- their scones are amazing!

The Lot

This is quintessential Bend, Oregon. It’s not a restaurant -- it’s a collection of food trucks with patio seating in the middle.

The Lot isn’t some asphalt parking lot with a bunch of picnic tables in the middle -- this place was developed just for this. They can heat the patio; garage doors open to let the air circulate on warm days; you can sit under the overhang or out in the open -- they have outdoor seating solved for all seasons. There’s also a bar with 16 taps, so you can try some of the local beers or ciders while you choose which food truck you want your meal from.


This is another restaurant that grew out of a food truck. You’re visiting Bend, so you’re probably not looking for a typical sit-down restaurant. But you are looking for great food, and that’s what Spork provides.

It’s a very unique space with very unique food. It can best be described as global street food, with dishes inspired by the chef’s travels all over the world. A New York Times review called it “culinary magic,” so you know you’re visiting one of the great restaurants in Oregon.

Where To Shop In Bend

The best shopping in Bend is right downtown. There are basically 12 city blocks -- from Franklin to Greenwood Avenue and Brooks Street to Tin Pan Alley -- where you will find a full day’s worth of shopping. As mentioned above, parking can be tricky, but try the lot off of Franklin Avenue over by the river.

I recall a lot of the great shopping being on that end of downtown, right by that parking lot (I believe the signs say Mirror Pond Parking Lot -- look for the public parking signs off of Franklin). Several great shops are located right there off of Brooks Street.

The Oxford Hotel in Bend, Oregon.

Best Places To Stay In Bend

Bend might be the Airbnb capital of the West. I remember looking for a place to stay and finding place after place on Airbnb -- some of them cottages and backyard Airstream trailers built just for Airbnb guests. I keep saying that Bend is a unique place, so why not stay in unique lodging?

If you’re looking for a more traditional hotel and are interested in spending a lot of time downtown, check out the Oxford Hotel. Great rooms, incredible amenities, a perfect location -- it has everything you’re looking for and more.

Did You Know?

One final fun fact: Did you know that the last remaining Blockbuster in the United States is in Bend? In early 2005, there were more than 5,700 Blockbuster stores in the U.S. Today, there’s only one.

So if you’re feeling a bit nostalgic (as in, nostalgic for 12 years ago), check out the Blockbuster near the corner of Revere Avenue and 3rd Street (right behind the gas station). Considering how quickly the world moves these days, it’s a trip back to a not-so-distant past when a Blockbuster on every corner was the norm.

Vacationing in Oregon? Read up on: