Over Labor Day weekend we took our first vacation as a family of four to Bend, Oregon. We had planned a trip to Bend years earlier for Valentine’s Day but were turned back by snow, so it felt extra special to finally visit with our boys. Bend is an inviting town with plenty of family-friendly activities, beautiful scenery and great food and drink options.
As much as we were looking forward to the trip, it almost didn’t happen. The kids caught a stomach virus the week before, which I then picked up the day before we left. I was feeling awful and a six-hour drive did not sound appealing. We couldn’t get a refund on our Airbnb and expected I’d be better the next day, so Kevin handled getting the kids packed while I rested, and we decided to go. The first day of our getaway happened to be our five-year anniversary, so despite my being under the weather we wanted to make it a memorable day.
The drive into central Oregon is stunning, especially south of Portland as you move deeper into the state. Views of Mt. Hood, long stretches of evergreens, and wide open skies made the drive scenic and enjoyable. We’ve driven to Oregon several times and often hit traffic, but the return trip usually goes more smoothly.
After checking into our Airbnb, we let the boys relax and stretch after the long ride. We then went to Trader Joe’s to stock the kitchen and picked up an early dinner. When traveling with young children we find two things make a big difference: staying in an Airbnb and eating out only once a day. A two-bedroom condo gives the kids room to nap and sleep at their usual time while allowing adults some downtime. A kitchen lets us prepare stress-free breakfasts and lunches, and a single dinner out keeps evenings manageable. Our rental had a loft and two bedrooms; the boys shared a room for the first time and did great.
For our anniversary dinner we tried 10 Barrel Brewing Company. The food and beer were fine, but it wasn’t our favorite spot on the trip. In hindsight, after a long drive we probably should have eaten at the rental so the kids could rest, but we wanted to go out for the occasion. Next time we’ll likely opt for an in-home meal the first night after a long journey.
After a good night’s sleep we were ready to explore. Our first full day started with a drive up toward Mt. Bachelor. With older kids we might have taken the lift for mountain-top views, but it was still nice to see the slopes up close. We then visited Drake Park along the Deschutes River where people were paddle boarding, canoeing, and floating. Before sampling beers, we stopped at Humm Kombucha for a tasting and then returned to the condo for the boys’ lunch and afternoon naps. In the early afternoon we tasted beers at Boneyard Beer and Cascade Lakes Brewery — the cherry blonde ale at Cascade Lakes was a highlight.
Returning for the kids’ naps meant missing some sightseeing, but from experience an overtired vacation makes everyone miserable. An afternoon break lets the kids recharge and gives the parents time to relax, so we consider it crucial to balance activity with downtime.
When the boys woke up we visited Deschutes Brewery’s tasting room. Deschutes is one of Bend’s best-known breweries, and the tasting room offers a convenient way to sample several beers. From there we enjoyed an early dinner at Barrio, which I’d recommend. After dinner we returned to the rental so the kids could go to bed.
Sunday we spent time at the High Desert Museum and were impressed by the outdoor exhibits, historical displays, and a birds-of-prey program where we saw bald eagles close up. The museum is engaging for both kids and adults and is definitely worth a visit. After the museum we stopped at Sparrow Bakery for pastries — their ocean roll is a memorable treat — and later visited Crux Fermentation Project, which ended up being our favorite brewery. Crux has a large space, a full menu and food trucks, so it’s easy to spend a relaxed afternoon there.
After another nap we visited Good Life Brewing, a welcoming spot and our fifth brewery stop. We decided to bring dinner back to the condo rather than eat out again; we ordered from Spork and enjoyed flavorful dishes like a shredded pork rice bowl with cucumber salad that I finished entirely.
On Monday morning we had breakfast at Chow. I had a crispy polenta cake topped with spinach, olive tapenade, a poached egg and béarnaise, with bacon cheddar grits on the side — one of the best breakfasts I’ve had. Chow is also open for lunch and is highly recommended when visiting Bend.
The drive home was smooth with only light traffic and one stop. There’s so much to do in Bend we could have stayed longer, but it was nice to be home and see the boys happy to sleep in their own beds.
Bend offers even more for travelers without young children: in summer there are countless hiking trails and Crater Lake National Park is about two hours away; the Deschutes River provides water activities; and in winter there’s skiing, snowboarding and snowshoeing. Beer lovers can follow the Bend Ale Trail to visit many local breweries, and the area also has wineries and excellent restaurants.
Even though it took us a while to make the trip, Bend did not disappoint. It’s a wonderful destination for both romantic getaways and family vacations. We left impressed with this oasis in central Oregon and look forward to returning.
