A Perfect 5-Day Oregon Road Trip

If you’re thinking of sun, sun and more sun (and who isn’t, at this point?), you’ll probably find warm weather and bright days in Oregon. I’d like to offer this Oregon Family Road Trip for your consideration. We went on this 5-day getaway last year over Labor Day weekend (plus a few more days) and had a lovely time – although you could also do this over Memorial Day or during summer break.

Day 1 of your Oregon Road Trip: Mt Hood

Drive from your starting point eastward toward Mt. Hood. Pull over at Bob’s Red Mill Whole Grain Store (right outside Portland, in Milwaukie). This grainy emporium features a giant waterwheel, real mill-grinding stones, great breakfast and lunch in the café and plenty of snacks for your Oregon road trip. I know it seems goofy to visit a store, but this store is pretty cool. Let kids pick a snack or two (gluten-free or not) from the bulk bins and enjoy a lunch, either from the second-story dining area or on the outdoor patio.  

Playing on the lawn outside Bob’s Red Mill Store

Stop off at Mt. Hood’s village of Government Camp and visit the Mt. Hood Cultural Center and Museum (check out the teeny-tiny mountain-climbing boots belonging to an elementary-aged kid). Or enjoy the kid-friendly birdwatching, hiking, wildflower-photographing (no picking!) or mountain biking on Mt. Hood. Read more about summer activities at The Village at Government Camp site.

Stay overnight at Timberline Lodge. Read more about our family accommodations at Timberline.

Day 2 of your Oregon Road Trip: Bend

Snow-covered mountain caps gradually fade into fir forest and grassy pasture, before flattening out into Central Oregon’s sun-kissed topography. Deep-green leafy trees cluster along riverbanks and wildflowers pop out of the most unexpected roadsides.

For an optional stop between Mt. Hood and Bend, pull over at Kahneeta Resort & Casino and visit the museum’s traditionally designed encampment (read more about staying at Kahneeta at Milagros Boutique’s blog). Or you can pull out a gallon of sunblock and visit the always-hot Smith Rock State Park, where rock climbers scamper up the face like tiny lycra-clad spiders. Wade in Crooked River’s banks, and show kids “Monkey Face,” a 350-foot-tall rock formation that resembles a primate’s mug.

Continue on until you reach the compact, turn-of-the-century-quaint town of Bend. Lunch at a family-friendly restaurant (our pick: The airy, spacious, healthy-but-delicious Deschutes Brewery).

Then, stretch your legs on Bend’s streets: Children’s clothing stores, bookstores, toy shops and two candy and ice cream shops (Powell’s Sweet Shoppe and Goody’s Soda Fountain and Candy) pack the downtown grid.

Pick up food at a grocery store before heading to your Bend condo or resort; the on-site food options are typically expensive and mediocre. My family gives eight thumbs up to the deli salads and quick-cook pizzas from the Bend Whole Foods. Most of these stores are clustered in Bend’s suburbs, along Highway 20.

Staying in the Bend family-friendly Sunriver Resort:

We stayed at the Sunriver Resort in one of the condominium vacation rentals. The kids loved Sunriver, and I have to say, the adults loved it too.  Among the attractions: Three outdoor pools (and one indoor pool), a fascinating observatory and nature center (my kids and husband went on a four-star “family owl walk”), a kids’ camp (Ft. Funnigan) that runs through both day and evening, an arcade, bike paths that line the river and weave through pine forests and horseback riding.

Take a VERY close look at the condo vacation rentals before committing to your purchase. Each rental is decorated and maintained at different standards. Our first rental was unacceptable to me (sort of mildew-smelling, mold in bathroom, oven will burn kids) and I asked to move to a different property. The second property was immensely better.

Also, familiarize yourself with the Sunriver map. If you think you’ll mostly be hanging out in your room, biking the trails or out in the surrounding area, it’s fine to be located further from the main lodge area. But if you have young children that tire easily or you want to be able to access the pools, try to stay near the Lodge area (lodge guestrooms, rentals in the Tennis Village Condo areas). The new, upscale Caldera Springs area is incredible, if your budget can afford the expense or if you’re sharing the cost with another family.

Bring your bikes or shop around on-site for the best bike rental prices, and do not neglect to check out prices in the Sunriver Village Mall. Prices (per day or multi-day) vary tremendously, and you’ll kick yourself if you pay far more than you should.

Check the Sunriver vacation packages and deals page. Accommodations aren’t cheap, but they’re worth it. Really, they are. I like this property far better than I like Washington’s Suncadia (sorry, Suncadia). On the resort’s website, you can sign up to be included in deal e-mails.

Do I need to add that my kids are now nagging me to death to return to Sunriver Resort? No, I do not. Endlessly. They. Nag.

Day 3 of your Oregon Road Trip: Bend Environment

You may want to chill at the resort for the morning (hey, did you see that list of things to do?). In the afternoon heat, think about escaping to two cool spots that are unique to our region:

Lava once scoured and scorched this area of earth. But that lava now provides you with an always-chilly escape into the earth’s basement. Pack a sweater and jeans, sturdy shoes and a flashlight (One flashlight for EACH MEMBER of the family. I am not kidding about this) Then head into the dank, dark lava caves at Newberry National Volcanic Monument.

It is pitch-black once you get deep inside and you cannot even see your hand in front of your face; see, aren’t you glad you brought so many flashlights? Not a place for young children terrified of the dark, but a great exploratory experience for big kids and their fraidy-cave parents. Lamps can be rented at the monument, but it’s better to just bring your own.

The High Desert Museum is incredible. A toddler- and preschooler-friendly play area entertains little ones, while the Volcano Country exhibit handily beats boring school geology discussions.

You’ll also learn about local flora and fauna and Central Oregon’s wild history in a glossy, contemporary building. Outdoors, a heavily shaded area shelters a working replica of a lumber camp; on high-traffic days, you’ll even see period-dressed men recreating the planing of timber.

A top-notch historical museum with a calendar full of family activities.

Day 4 of your Oregon Road Trip: Eugene, Oregon

Today, you return to Oregon’s western through a gorgeous evergreen route. Before hitting the road, eat breakfast at Alpenglow Cafe, which serves up real maple syrup alongside generous portions of homestyle pancakes, homemade breads and locally-smoked meats. Oregon family-friendly and Oregon farm-friendly can’t be beat. Of course, there are plenty of vegetarian options as well (this is the Pacific Northwest, after all) — you can even sub in tofu for those farm eggs.

In my opinion, the best way to go from Eugene to Bend is to take the 2.5 hour, two-lane Highway 26 route, which pulls you through the western-style town of Sisters, Ore., before shooting you over the mountains. You’ll enjoy ear-popping mountaintop panoramas before descending into Western Oregon’s verdant firs and deciduous trees.

Now that you’re in Eugene around midday, what will you do? Check out this family guide for 15 fun things to do with kids in Eugene, Oregon.

Sniff! Are you sad about going home yet?

I loved writing this trip report up and can’t wait to repeat this trip. Does your family have a favorite Oregon road trip itinerary?