Knock, knock. We know you’re in there—and look, we get it. You’re not in the mood to escape your cocoon of wool blankets, nor are you ready to forgive the delinquent sun for departing so abruptly way back in October.

But psst—crocuses are emerging from the dark earth. Daphne perfumes the air. And, yes, that is actual sunshine on your face. A spring day trip will fast-track your revival while reacquainting you with the splendors that sit just outside of Portland. So throw off those blankets, because it’s time to wander serene oak groves in the Yamhill Valley, admire the charming street art of Silverton, and road-trip the Oregon Trail.

An Outdoor Gallery

Down the Willamette Valley, a skosh east of Salem, quaint Silverton counts more than 35 murals adorning the facades of its historic downtown buildings. While not exactly provocative art, they celebrate the town’s legacy as a bustling mill and banking center in the pioneer days of Oregon. 

Begin with the 70-foot-long mural honoring Bobbie the Wonder Dog, perhaps the most famous canine in Oregon history. In 1923, Bobbie went missing while his family was visiting relatives in Indiana. Six months and 2,800 miles later, he limped back to the front stoop of the family’s Silverton farm. The mural documents Bobbie’s ascent to national stardom; spot letters from the editors of National Geographic and posters from his own silent movie. Even Rin Tin Tin made it to Oregon to lay a wreath at his grave.  

From here, the rest is up to you. (You can download a map from the Silverton Mural Society.) Maybe you’ll run into portraits of Homer Davenport, the world-famous, turn-of-the-century political cartoonist, or June Drake, the local photographer who regularly dragged his equipment to Silver Falls and successfully lobbied the Oregon Legislature to make it a state park (it’s just a 20-minute drive away). Don’t miss the tribute to Silverton’s fallen Oak—a frank and moving indictment of pioneer hubris—or the triptych ode to the Silverton Red Sox, among them Oregon-born Johnny Pesky, a future all-star for the Boston Red Sox. 

Between mural stops, drop into antique shops—find retro knickknacks and restored pioneer furniture at Homestead Relics Vintage Market—and refuel with harissa steak tacos on Noble Fox’s riverfront patio. Then drive a mile to the Oregon Garden, home to the state’s only Frank Lloyd Wright house and 80 acres of native trees, shrubs, and blooms such as crocuses, magnolias, tulips, and columbines.

On the way home, cap the day with a wine tasting at St. Josef’s in Canby. Or if you’re not ready to leave, bunk at McClaine House, an 1878 Victorian in downtown Silverton that was originally home to one of the town’s first bankers. A multicourse breakfast awaits in the morning.

Into the Oak Savannas

Just 40 minutes southwest of Portland, between the wine country towns of Carlton and Newberg, sits Our Lady of Guadalupe, a Trappist abbey home to 14 monks. In addition to managing a wine warehouse, hosting retreats, and baking fruitcakes (sold on-site as well as on Amazon), the monks maintain about four miles of easy trails that invite quiet contemplation as they wind through one of the few remaining oak savannas in Oregon.

The monks encourage silence (sorry, no dogs) so not to disturb meditation, but it’s tough not to release a joyous yawp at a landscape that seems to belong to another century. In fact, about 200 years ago, oak savannas spanned 400,000 acres in the Willamette Valley; the Kalapuya people staged controlled burns to discourage invasive plants and maintain productive breeding grounds for the area’s wildlife. Today, only 20,000 acres remain. 

Watch for woodpeckers and barred owls as you enter the forest, staying on Our Lady of Guadalupe Loop Trail as you navigate switchbacks to the top of the ridge. Once the ground goes flat, go right and enter a William Stafford poem. A wide path leads to a brick shrine—visitors leave tokens of gratitude for the Lady of Guadalupe, an iteration of the Virgin Mary—and a view of the valley below. Keeping to the path, descend through tracts of forest and farmland before lollipopping back.

As lunchtime approaches, hightail it 15 minutes for a roast beef sandwich or Cobb salad at Dundee’s much-loved Red Hills Market. Or maybe you’re ready to visit Worden Hill Road, the Yamhill Valley’s mini version of Napa’s Silverado Trail, for a flight of local vintages. Pair wood-fired pizza with pinot noir at Furioso Vineyards, and don’t sleep on the chardonnay at Cramoisi Vineyard.  

To make it a weekend, book a suite in a refurbished silo at Abbey Road Farm, just across the street from the abbey, or curl up by the stone fireplace at Franziska Haus, a B&B in Dundee known for its German-style breakfasts.

Barlow Road or Bust

In 1846, Samuel Barlow opened an overland pass across the south flanks of Mount Hood for emigrants and their covered wagons on the Oregon Trail. Without access to dynamite, workers used axes, saws, and controlled burns to widen the original route, which the Chinook, Wasco, Warm Springs, Molalla, and others had traveled for centuries. Before the embellishing, most settlers had to wait in The Dalles to load their wagons onto rafts for a perilous float down the Columbia River to reach the trail’s end in Oregon City. Spring is the perfect time to retrace this road, with its pioneer graves and mountain meadows that shimmer with lupine, monkeyflowers, and rhododendrons. (This itinerary guides you in the reverse direction and, due to seasonal road closures and snow, is best saved for April or beyond. Check conditions before setting out.)

As you motor out of town on US 26, nab a no-frills Boston cream at Joe’s Donuts in Sandy before a pit stop at Pioneer Bridle Trailhead in Rhododendron, where you can trace your hands over a replica of the trail’s final tollgate. (In 1883, travelers paid $5 per wagon, about $200 today.) Pause to admire the towering maples, believed to have been planted by the original tollkeeper. 

Ten minutes farther is Laurel Hill. Between mileposts 50 and 51, look for a brown sign and then park in the pullout on the south side of the road. Climb the stairs to a decommissioned stretch of highway (it dates to the 1920s). To the right, you’ll see a chute where, 150 years ago, settlers had to drag huge logs under their wagons to slow their descent down the steep grade. Another 100 yards farther, a hiking trail guides you on a quick saunter up a ridge to the intersection with the original Barlow Road and the very top of this infamous chute.

Just like a nineteenth-century settler or an ’80s kid on an Apple IIe, you now have a decision to make. After turning north on OR 35, do you make a stop at Barlow Pass, hike two miles to the Pioneer Woman’s Grave, and picnic in the adjacent meadow bursting with lupine and yarrow? Or do you wait until you’ve traced more of the Barlow route and sputtered over the mountain on Forest Road 48 through Wamic, where the very first tollgate was erected, and enjoy your picnic in a grassy meadow at White River Falls State Park? If you opt for the latter, you can take a steep, rocky trail—not suitable for wayward children—for a view of this gorgeous two-tiered waterfall as well as an abandoned hydroelectric station that sits like an open-air museum at the bottom of the falls.

Continue north on US 197 through Dufur, where, if you want to make it an overnight, the 118-year-old Balch Hotel invites with antique charm and gracious hospitality, including freshly baked cookies at check-in (the on-site restaurant is good, too). Or keep on trucking to The Dalles, popping into Klindt’s, the oldest bookstore in Oregon, before tackling a behemoth cinnamon roll at road-trip staple Cousins’ Restaurant & Saloon. Follow the river home on I-84, a road Sam Barlow surely couldn’t have fathomed.