Eastern Oregon Loop with 4 Wonders Road Trip
5 days/4 nights

Day 1 - Portland to Emigrant Springs State Heritage Area
233miles/3.5 hours
Leave the city behind for the breathtaking Columbia River Gorge - the first Oregon Wonder you’ll see on this trip. Oregon’s tallest waterfall, Multnomah Falls is 30 minutes east of Portland and is visible from I-84. Tickets are now required during peak season and can be purchased at Recreation.gov. The area around the falls remains scorched by the Eagle Creek Fire in 2017 and some hiking trails may be closed. A beautiful alternative is the nearby Latourell Falls which is the third tallest waterfall in the Gorge. At 2.1 miles and a 643 elevation gain, it is rated as moderate (good for older kids). Not to be missed is the historic Vista House which offers breathtaking views of the Columbia River Gorge.

As the landscape changes from lush greenery to rolling desert hills, keep your eyes out for one of the hundreds of wind turbines dotting the crests of the Gorge. Towering above the ground at a height of 280 feet (that’s more than a 30 story building!), these enormous wind turbines generate about 12% of Oregon’s energy production. You’ll also notice along the Columbia River the Bonneville, Dalles and John Day dams. These beastly, concrete behemoths help Oregon generate almost half of its energy production from hydroelectricity. As you drive the final stretch of today’s road trip into Pendleton, you’ll see one of Oregon’s solar farms off to the side of the highway. As you might have suspected given western Oregon’s rainy reputation, solar energy makes up only about 2% of Oregon’s energy production.

Pendleton offers some great city parks if you have kids. Pioneer Park (400 NW Despain Ave, Pendleton, OR 97801) is a great spot to let kids stretch their legs. Next, consider a stop at the nearby historic Pendleton Mill Store for a tour and a little shopping. For over a hundred years, they have made the iconic woolen Pendleton Blankets that permeates western décor. Granted, these beautiful works of art are not cheap. Even so, you just might find yourself a bargain.

Enjoy dinner in Pendleton then make your way to Emigrant Springs State Heritage Area for the night. To save space in your car, consider renting one of the six rustic cabins.

Day 2 - Emigrant Springs State Heritage Area to Baker City via Joseph, Oregon
208 miles/4 hours
Today you are in for a special treat - the second and one of my favorite Oregon Wonders, the Wallowas! Continue driving east for about 30 miles to La Grande. Stop here for some breakfast then take a walk through the historic downtown. Back in your car, head north up to the quaint town of Joseph. I know you want to stop, but keep going because you’re almost there. Ta-da! Look at that! Beautiful Wallowa Lake is set like a dream at the base of the Wallowas. They call this Oregon Wonder the Oregon Alps. And this morning, you are going to do a little mountain climbing without even breaking a sweat. Head over to the Wallowa Lake Tramway, purchase your tickets and soar like an eagle to the top of Mt. Howard. At 8, 150 feet in elevation, the view is absolutely breathtaking. Take the easy 1 mile Wallowa Lake Tramway Trail to soak in spectacular Oregon Alps.

Wallowa Lake State Park sits right on Wallowa Lake and is one of my favorite places to camp. If you’re able to extend your trip a day or two - this would be the perfect place. The lake offers boating, kayaking, fishing and swimming. You can also make a day trip from here to Hells Canyon Overlook to see the deepest canyon in the US (yup, it’s deeper than the Grand Canyon).

Now if your epic view happens to be obstructed by clouds or wildfire smoke, don’t worry. Chocolate is the perfect antidote to disappointment. And Joseph happens to be home to Arrowhead Chocolates which serve up little bits of heaven that melt gloriously in your mouth. In fact, even if your views were epic, you still can’t miss this place. Joseph itself is special. You will feel it as you walk through the heart of this quaint, historic town. Joseph is especially known for its bronze sculptures which bring the streets to life. If it’s eating time, stop here for a delicious meal.

There are two hours to go until Baker City where you can stay at the historic Geiser Grand Hotel. I am a sucker for historic hotels and there are some pretty cool things to see here. Just expect that it won’t it won’t be modern - because you know, it’s historic. Based on our experience, I recommend calling them to book directly rather than booking through a third party site. Camping options include Catherine Creek State Park which is about 45 minutes north of Baker City and Farewell Bend State Park which is about 45 minutes south of Baker City.

Day 3 - Baker City to Clyde Holliday State Recreation Site
86 miles/1.75 hours

Today you are going to time travel. Start your journey in the mid-1800’s at the National Historic Oregon Trail Interpretive Center in Baker City. Learn what it was like to be one of the 400,000 people who walked more than 2,000 miles into the unknown in search of a better life. Allow 2-3 hours to explore the center and it’s outdoor exhibits. And by all means, grab your water bottle and go see the wagon ruts outside!

Now it’s going to get real. You are going to take the Journey Through Time Scenic Byway. I am not making that up. It is really called that. I told you we were going to time travel! Travel south from Baker City to Highway 7 where it all begins. As if time travel didn’t sound magical enough, you will be driving into the Strawberry Mountain Wilderness to discover gold mines, a ghost town, and a thriving 1800’s Chinese community.

Here we will take a break from our time travel to settle in at Clyde Holliday State Recreation Site. This is the only place in the Oregon State Parks system where you can rent a teepee. Teepees sit on a concrete pad and come with vinyl sleeping pads for up to eight people. This was a really great experience for a group of 4th - 6th graders on a summer road trip around Oregon. This was a really bad experience during cold, rainy weather with a 2nd grader who had no fear of the raging John Day River behind the teepee. Choose wisely, my friend. The campground also has 31 electrical sites with water that are first come first served. Prineville is another option for lodging. Cell service is spotty at best through this stretch so best to plan ahead (you know, just in case a major event in town has all of the hotel rooms booked, for example).

Day 4 - Clyde Holliday State Recreation Site to Timberline Lodge
206 miles/4 hours
Today is a day of wonders. That’s right, plural. Today you get to see not one but two Oregon Wonders! The first spectacular wonder of the day is the Painted Hills at John Day Fossil Beds National Monument. Now, let me first say that the John Day Fossil Beds is a huge monument with three separate units plus the Thomas Condon Paleontology Center which I hear is a fossil hunter’s dream (insert frowny face with a rained out teepee emoji here). From what I read about the place, if geology and paleontology are your jam, you can rock out here all day.

Since we only got to see the Painted Hills, I will tell you that they were amazing - even during a cold rain. You are guaranteed to take about a hundred pictures. They are all going to look pretty much the same but still you’ve got to take them. There are five short hiking trails at the Painted Hills Unit as well as a picnic area and vault toilets. The gravel road to the Painted Hills has its twists and turns but is otherwise well maintained.

Now, just when you thought it couldn’t get any grander, you are off to your fourth and final Oregon Wonder for this road trip - Mt. Hood! You have a three hour drive ahead of you so break it up with a stop at the Museum at Warm Springs. This is a great museum celebrating the history, art and culture of the three Confederated Tribes of Warm Springs. But first, see if you can find the door! Maybe we’d been driving too long but it took us a minute. Once inside you will find interactive exhibits and probably the most beautiful beadwork and basket weaving you’ll see anywhere in the world. Plus there are huckleberry treats in the gift shop!

You’re only an hour away from the fourth Oregon Wonder, and by now you’re probably catching glimpses of it off in the distance. Wy’East, as it was named by the Chief of the Multnomah Indians (or maybe by Frederic Homer Balch in a work of fiction in the late 1800’s) is Oregon’s tallest mountain at 11,250 feet. Besides just being breathtakingly beautiful, Mt. Hood is the second most climbed mountain in the world after Mt. Fujiyama in Japan. It offers world-class skiing and the longest skiing and snowboarding season in the country (Olympic athletes train here, you guys!). The area is a mecca for summertime hiking and includes parts of the famous Pacific Crest Trail. Plus there are all kinds of outdoor adventure activities to be had in and around the area. But today, we are going to hang out at the historic Timberline Lodge.

This place is really cool! Built in 1938 with funding from the Works Progress Administration (WPA), this Depression era lodge is as much a work of art as a labor of love. Craftsmanship oozes from every corner of this place. Seriously - it is unbelievable the amount of thought and care that went into building Timberline Lodge. It is just one of those places you just have to see - and eat at, and spend the night at. Even if time or budget doesn’t allow for food or lodging, you should take the self-guided tour. The lodge is open to everyone and receives nearly 2 million visitors a year so don’t worry about imposing.

We like renting the Chalet Rooms which sleep 2-10 people. These simple rooms have bunk beds, sometimes shared bathrooms and are a fraction of the price with full access to the amenities. It is a great place to meet up with family and friends and explore the mountain together. If you have kids, make sure to do the Timberline Lodge scavenger hunt! Ask for details at check-in. It is a great way to learn more about the history and culture of the area - and at the end you get a prize! My kids got some cool retro metal lunch boxes that they were pretty darn proud of.

As you might imagine being right smack in the middle of a national forest, there are also a ton of camping options. Trillium Lake Campground is a great option for families and those who love looking out over a beautiful lake and snow capped mountain. Sites at Trillium Lake and other area campgrounds can be reserved through Recreation.gov.

Whew! It’s been quite a day. No “wonder” you’re tired and blissfully happy. Rest up because tomorrow is the last leg of your journey.

Day 5 - Timberline Lodge to Portland
65 miles/1.5 hours
Today you are headed home. But depending on your bedtime there’s still a lot of adventure to be had! Before saying goodbye to Timberline Lodge, you have got to try the Magic Mile Chairlift. It was only the second passenger chairlift in the world when it was built in 1938 - and the longest chairlift in existence! Don’t worry, it has been replaced a few times since then. The views are fantastic and even in the summertime you can build a snowman!

Then, since we are in the Mt. Hood National Forest, I am going to recommend that you take a hike. One of my favorites is Tom, Dick and Harry Mountain via Mirror Lake Trail. I remember hiking this trail with my dad and sister when I was a kid. Now that I’m a mom, it was really special to hike this trail with my kids and their grandpa. That being said, it’s a 9 mile hike with a 1,709 foot elevation gain and your kids are probably going to need some heavy duty motivation. There are also a few drop offs to watch out for. A great alternative for families with younger children or folks looking for a shorter route is the Mirror Lake Loop Trail. This is basically the same trail minus the climbing a mountain part. Bring lunch to eat at the lake for an unforgettable picnic. The water is very cold here so you’re probably not going to do any swimming, but maybe bring a towel for brave feet.

Dusty, sweaty and feeling amazing, it’s time to get back in your car and continue down the mountain. Our family tradition is to indulge in a really sugary sweet after a hard hike, so by all means keep your eyes peeled for the perfect place to replenish those lost calories!

Now, I am willing to bet that this road trip has been an EPIC Oregon adventure filled with spectacular views, four Oregon Wonders, awesome hikes, great food and even a few thrills. So for our last stop of this amazing Eastern Oregon Road Trip, we are going to Boring, Oregon. That’s right, Boring. Just for kicks you have to get some pictures - like how about at Boring Middle School? Supposedly Disney’s Gravity Falls was inspired by this Oregon town. Boring is also home to the North American Bigfoot Center and is sister cities with Dull, Scotland and Bland, Australia. You can’t make this stuff up!

And there you have it, an epic Eastern Oregon Road Trip! As always, be sure to check local resources for weather, road conditions and COVID-19 related closures when planning your trip. And don’t forget to post your photos to #lifelivedoregonstyle on Instagram. We’ll see you out there!