DAY 1: Portland to Mt. Hood
Maple-bacon-wrapped dates, a fried-egg sandwich, a side of biscuits with huckleberry jam—from the spread in front of us, you’d think my family and I are fueling up for a triathlon. In truth, the only physical activity we have planned between now and lunch is a quick waterfall hike, but we’re at Tasty n Sons, a Portland brunch institution, and when you’re here, you eat (tastynsons.com).
Tasty n Sons is our launch point for our road trip from Portland to central Oregon. Our mission: to convince our almost-5-year-old son, Theo, that road trips are the best trips so that he and his younger brother, Baxter—who, for now, follows Theo’s lead in every way—will happily pile into the car anytime we want to explore our country. If we fail? We set ourselves up for years of are we there yet?” pleas from the backseat.
As we head east on Highway 84, Darrell talks up our first stop, telling the kids all about Multnomah Falls, a 611-foot-tall waterfall a quick 40 minutes outside of Portland. A secret spot this is not—2.5 million people visit the falls each year—but that doesn’t make it any less spectacular. Theo is appropriately awed when we step out of the car and get our first glimpse. His only disappointment is that we can’t get right up next to the actual water—a sentiment I anticipated, which is why I choose Horsetail Falls as our next stop.
There’s not an official count of waterfalls in Oregon, but there are at least 238, and likely more. Horsetail Falls is one of my favorites for a few reasons. For starters, getting there requires a drive along Historic Columbia River Highway, a narrow two-laner covered by a canopy of evergreens. And then there’s the hike in—an easy 15-minute climb of switchbacks that stops you in your tracks with surprise views of the Columbia River Gorge. But the waterfall itself is the real draw. The falls shoot out in the shape of a horsetail, and hikers can walk not just right up to the water but also behind it, thanks to a cave-like overhang in the rocky bluff. On warm summer days, the pool formed by the falls is a playground for swimmers and their dogs, but temps today are in the mid-60s, so we settle for dipping our toes in the chilly waters.
By the time we get to Hood River, a small town whose placement on a bend in the Columbia River draws windsurfers from around the world, we’re ready for lunch. Pfriem Family Brewers feels tailor-made for us, with seasonally inspired pub fare—including a children’s menu with more than just mac and cheese—and a corner toy area where kids can play while their parents finish their IPAs and fresh-hop brews (pfriembeer.com). The brewpub is also in the ideal location: right across the street from Hood River Waterfront Park, where the kids’ climbing wall, seesaws, and swimming beach make for the perfect place to work off road-trip energy (hoodriverwaterfront.org).
Fed and happy, we wind up Highway 35, a quiet road that leads away from the river to The Gorge White House (thegorgewhitehouse.com). The historic house and farm is on the Fruit Loop, a 35-mile drive in the Hood River Valley dotted with U-pick farms, wineries, and farm stands with views of Mt. Hood in all its glory, all 11,250 feet of it (hoodriverfruitloop.com).
Again we’ve anticipated Theo’s reaction: “But can’t we play in the snow?” And so we’re off to Timberline Lodge, the only ski area in North America with year-round skiing (from $260 per night, timberlinelodge.com). As we check in, Theo and Bax are out the back door and falling backward blissfully into the powder.
We’ve barely traveled more than 100 miles, but we’re more than happy to have Timberline as our home for the night. It feels exactly how a mountain lodge should: rustic, sturdy, and with three gargantuan fireplaces at the base of the 90-foot stone chimney, cozy.
DAY 2: Mt. Hood to Bend
We let ourselves linger at Timberline for the morning. The lodge’s Cascade Dining Room can feel a little formal during dinner if you have young kids in tow, but the breakfast buffet is easy and casual. We pile our plates with farm eggs and freshly baked muffins, and then head outside to the Pacific Crest Trail. Depending on which direction you go, the path will take you as far north as Canada or as far south as Mexico, stopping at each border. Today we settle for an easy walk, pausing every two minutes for the kids to “discover” another rock or hunk of moss.
The transition from the west side of the Cascades to the east side is always a surprise, even for those of us who’ve made the trip before. In a matter of just a few miles, the lush vegetation and skyscraping evergreens are replaced with a high-desert landscape of sagebrush, juniper, and crackled dry dirt. Tumbleweed bounces across the road as we make our way east on Highway 26.
This is the longest stretch of our trip—90 miles from Timberline to Smith Rock State Park—and the kids are itching to run by the time we pull into the park entrance. We’re immediately endeared by the welcome center, an unassuming hunter-green yurt, and we duck in for advice on kid-friendly hikes. The ranger suggests walking along an easy trail that will give us up-close views of Smith Rock, a towering monolith formed from a volcano’s ash explosions a half million years ago.
Sure, Smith Rock is especially popular among rock climbers, but this place is for everyone—photographers mesmerized by the golden light on the rock face, families hoping to spot a river otter or golden eagle, mountain bikers looking for an adrenaline rush. We’ve brought a picnic to maximize our outdoor time and avoid wrangling the kids in yet another restaurant. We coax the boys back in the car with the promise of huckleberry ice cream from Juniper Junction, which Darrell and I spotted just outside the park’s entrance on our way in. Ice cream in hand, we set off for Bend, just 25 miles south on Highway 97.
I’m not usually one to waste valuable vacation time inside a hotel, but I make an exception at McMenamins Old St. Francis School (from $170 per night, mcmenamins.com/oldstfrancis). The McMenamin brothers are famous in Oregon for two things: being instrumental in pushing through a 1980s Oregon law that allowed breweries to sell their beer on the premises (hence kicking off the region’s craft-brewery craze), and restoring abandoned buildings like schools and churches and turning them into hotels and brewpubs. Old St. Francis School was, just as its name implies, a Catholic school. The McMenamin brothers bought the building in 2000 and turned it into a hotel, keeping so much of the original character you’d swear you need a hall pass when you walk down the long corridor. The big draw, for me at least, is the mosaic-tiled soaking pool. My family and I suit up and climb in. The warm saltwater recharges us, and by the time we get dressed, we’re ready to hit the town.
With Mt. Bachelor in the distance and the Deschutes River running through it, Bend feels like the quintessential outdoorsy town. Polar fleece is acceptable attire anywhere you go, gear shops abound, and the town boasts tons of breweries. We’ve heard rave reviews of the beer at Crux Fermentation Project, and when we learn it has an outdoor area with a fire pit and cornhole setup, we’re sold. The kids improvise their own cornhole rules, and Darrell and I actually get a (very) rare20 minutes to talk only to each other. Small victories, but we’ve learned to take them whenever we can.
DAY 3: Bend to the Lodge at Suttle Lake
The next morning I practically bound out of bed in anticipation of breakfast. We’re going to the original Sparrow Bakery, a tiny spot in the Old Ironworks District that churns out the most incredible pastries (thesparrowbakery.net). The morning is sunny and almost warm, giving us the perfect excuse to sit in the outdoor courtyard and enjoy the bakery’s famous Ocean Rolls, croissant dough rolled in cardamom, vanilla, and sugar and baked to flaky perfection.
We’re eager to get to The Lodge at Suttle Lake, almost an hour northwest of Bend along Highway 20. I’ve saved it as our last stop for a couple of reasons. The first is to soak up the property as it is now, a lakefront lodge and series of cabins that feel sweetly unsophisticated. The second is what the place is about to become. The team behind the Ace Hotel Portland recently bought it and are about to relaunch the property as The Suttle Lodge & Boathouse (thesuttlelodge.com). The character I love will remain, but the team will put their fun, design-savvy stamp on it, making it, as they put it, “a relaxed Cascadian forest lodge as imagined by a gently debauched scout.” There will be a beer garden with lawn games, a huge roaring fireplace to gather around for card games and spirit sipping, arts and crafts workshops, and canoe, kayak, and SUP rentals. In other words, summer camp for the whole family.
We’ve rented one of the stand-alone cabins for the night, and as we sit on the porch soaking up the fresh air and bright sun, I tell Theo about how we’ll be able to rent boats here on our next trip and ask if he’d want to come back. “Can we make it a road trip?” he asks, and Darrell and I actually high five each other. Mission accomplished.