A Three Day Weekend In Bend, Oregon

(Last Updated On: March 31, 2020)

I love weekend trips. To me it’s just the right amount of leisurely fun that gives me enough rejuvenation to take on another work week. I particularly enjoy destinations that take less than four hours to get to, whether its by car, train or plane. That’s why this post featuring how to spend a weekend in Bend, Oregon was an inevitable trip that I would take from Portland.

If you have read other posts on my blog you know how much I love writing about weekend getaways or short trips. One of my favorite cities to visit on the west coast is San Francisco. Check out the weekend itinerary here.

Recently, I had the opportunity to visit Bend and stay at the beautiful resort called Riverhouse on the Deschutes. It’s crazy to think that I have been living in Portland for over six and half years, and only visited Bend once. If you are an outdoor skier, hiker or biker you will surely enjoy the outdoor splendor of Bend. But hey, even if your not, you may be interested in kicking back with a craft brew or sipping a coffee in one of the many downtown establishments with friends.

So, if you are considering a weekend escape to this outdoor lovers paradise below is the itinerary of how I spent my weekend and if you are looking for extra activities, check out my full post written for the publication site

9:00 AM Saturday

My husband and I set out in our car for the three and a half hour drive to Bend with snacks and coffees in tow. There are two ways that you can drive to Bend that take the same amount of time. One is heading south from Portland on interstate 5 toward Salem and then getting off the interstate and heading east. We have taken that drive before, and I really enjoyed stopping through the western town of Sisters. But this time, we decided to drive through the Mt. Hood national forest.

10:00 AM

Driving east from Portland we headed straight through the small skiing community of Sandy, Oregon, an adorable town. One of those towns where all of the buildings are coordinated to have that alpine look. I really liked it.

As we continued on our climb on Mt. Hood my breath was taken away at the snow capped peak. I would not have attempted to drive this in the middle of winter, as we don’t have snow tires or chains and it wouldn’t have been safe. But in mid-March the roads proved to be clear.

Driving through the Mt. Hood National Forest.

12:30 PM

We arrived in downtown Bend just in time to grab some lunch. We parked very easily in the downtown area and walked to Deschutes Brewery, an established Bend Brewery and Pub.

Me enjoying my water at Deschutes Brewery before lunch arrives!

The beers on tap menu is extensive, and you can even order small 3 oz tasters. We opted out of beer tasting this early in the afternoon, but if that’s your thing there are many options to choose from. The most popular is the Mirror Pond Pale Ale.

Steak Salad from Deschutes Brewery in Bend, OR
Steak Salad from Deschutes Brewery in Bend, OR

Our lunch was delicious. I ordered a steak salad while my husband ordered a Mongolian beef over french fries. I tried his and can attest that it was equally as good as my dish.

Mongolian beef over french fries

The brewery and restaurant is very large, so whether you are traveling with a large group or just a few friends you can be accommodated.

2:00 PM

Time to get a caffeine boost. We walked a few blocks from Deschutes Brewery and got lattes at The Looney Bean.

Looney Bean Coffee, Bend, Oregon
Looney Bean Coffee, Bend, Oregon

Situated directly on the Deschutes River, this quaint coffee shop has a cute green space in the back that overlooks the river. Guests can sip at their leisure in lawn chairs in warmer months. In the winter the cozy cafe offers cafe tables and chairs for patrons to read the news and sip their cappuccinos.

Latte at Looney Bean Coffee

3:00 PM

For the next hour we had fun exploring the streets and waterfront of downtown Bend. We walked along the Deschutes River, did some shopping and people watching.

Walking through the park along the Deschutes River.

Steal The Bend Style

An artsy side street in downtown Bend.

4:00 PM

Time to check-in to Riverhouse at the Deschutes Hotel! But before we did that we attempted to drive to the Pilot Butte scenic lookout that is just a little over a mile from downtown Bend. Unfortunately for us the road to drive up to the top of Pilot Butte was closed for the season. But I recommend doing this in the warmer months.


As we drove towards our hotel we drove past a Blockbuster video. But not just any Blockbuster video, this happens to be the last Blockbuster video in the entire world. It is unclear how long this franchise will be a stronghold here in Bend, but for now locals and tourists are stopping by for photo-ops and soaking up some late 90’s and early 2000’s video store nostalgia. I couldn’t resist a photo-op myself.

The last Blockbuster video in the entire world…right here in Bend, Oregon.

4:30 PM

When we arrived at Riverhouse on the Deschutes our room was not ready so we sat down in the lobby bar, seats nestled along the Deschutes river and ordered a few local craft brews to pass the time.

Craft beers from Currents restaurant at the Riverhouse at the Deschutes hotel lobby bar.

5:00 PM

Time to check in! I always get a thrill of seeing the hotel room in person. A few years back Riverhouse on the Deschutes went through an extensive renovation to all of its rooms. I can attest that the result is fantastic. Our room overlooked the Deschutes river and was equipped with a Keurig machine, a large patio, a wood burning fireplace and luxurious soaps and shampoos!

Keurig machine and large countertop in our guest room at Riverhouse on the Deschutes.
A king size bed in our guest room at Riverhouse on the Deschutes.
A wood burning fireplace in a guest room at Riverhouse on the Deschutes.

6:00 PM

Dinner time! We had a reservation at the in house restaurant named Currents. Our service was outstanding and the food was top notch. Everything is made in house and most ingredients are sourced from local farms. We enjoyed the comfortable dining room and found our waitresses recommendations very helpful.

Salmon over black lentils and squash puree.
Chicken, pomme purre, green beans and ratatouille
French onion soup

8:00 PM

After dinner we walked by the heated pool and hot tub and pondered whether we should splash around for bit. It was very busy so we opted not to swim, but it did look really fun!

Sunday, 8:00 AM

Time to head back to Portland. With a three and a half hour drive ahead of us we figured we would make an early start back. But not without some food in our bellies.

We decided to go to McKay Cottage, just a short half a mile from our hotel. This place got an A+ for ambiance. Situated in a craftsman house, with year round seating outdoors makes this brunch spot a popular place with locals and travelers. In fact, it has been awarded the “best brunch in Bend” for 10 years in a row.

Outdoor seating at McKay Cottage

It just so happened to be St. Patricks Day so there were some corned beef specials and my husband happened to order one of those dishes while I selected coffee and eggs Benedict.

Coffee and in house pastry
Corned Beef Hash with eggs benedict
Classic eggs benedict

9:15 AM

With food in our bellies we were ready to hit the road and make our way back to Portland.

If you have more time to spare, I highly recommend heading to some of the outdoor splendors that Bend has to offer. Check out Mt. Bachelor for skiing and hiking, Smith Rock for rock climbing, Tumalo Falls for a waterfall hike and if your feeling extra adventurous check out one of the many natural hot springs around Bend.


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