← Quintessential Sauvie Island 

30 Minutes from PDX: Begin your day picking a bagful of ripe snacking berries at Bella Organic farm, then make your way to Cistus Nursery, where you can wander stunning display gardens and scoop up some hardy tropical plants. From there, head out to Walton Beach, where you can soak up plenty of rays and frolic in the Columbia River. Return via Sauvie Island Road for a languorous pit stop at Kruger’s Farm, where Thursdays bring live music, and weekends mean Captured by Porches microbrews and kielbasa sizzling on the grill.

Covered Bridges in Cottage Grove  

2 Hours from PDX: One of the state’s many quirky claims to fame is Cottage Grove, our “Covered Bridge Capital.” Six preserved bridges, the earliest built in 1925, dot the bucolic burg, and can be toured in just a couple of hours. Pack a hearty picnic (see above for inspiration) and complete the circuit, then stop by Agrarian Ales’ historic dairy barn on the way home to tour the hop farm, scarf down wood-fired pizza, tap your foot to live bluegrass, and sip one of the 11 beers on tap.

Antiquing in Aurora  

30 Minutes from PDX: In 1856, preacher Wilhelm Keil founded Aurora Colony, a Christian utopian society flush with musicians and crafters. Oregon’s first historic district still boasts many of its original buildings, but Aurora’s true appeal is in its antiques. Lose yourself in the three-story Main Street Mercantile for hours of scavenging, from turn-of-the-century china to solid-plank dining tables, before popping over to Aurora Mills Architectural Salvage for precisely organized doorknobs and Gothic church lights. Finish off with a flight of pinot noir in the Pheasant Run tasting room, housed in the historic Aurora State Bank building.

The Mount Hood Fruit Loop Tour 

90 Minutes from PDX: Prepare for the day’s indulgent ramble with nine holes of par-3 golf, Bloody Mary in hand, at McMenamins Edgefield. With some birdies under your belt, nibble your way through 35 miles worth of Mount Hood area farms, plus Instagram-worthy mountain vistas and sprawling wildflower meadows. Take a pulled-pork break at Parkdale’s Apple Valley BBQ before looping back along Highway 35 to meet cute with grazing alpacas at Foothills Yarn & Fiber/Cascade Alpacas, followed by crisp ciders with a view on the porch at Fox-Tail Cider’s tasting room. Toast your bucolic odyssey with a glass of easy-drinking Ruins Red at urban winery Springhouse Cellar (and fill up a growler to go). Stick around to hear local bands in the adjacent Ruins, the towering remains of an old distillery turned rubble-chic venue.

↑ Taste the Grapes in Dundee/Carlton 

40 minutes from PDX: These two tiny, rustic-chic farm towns, just over 20 miles from Portland, offer an immersive crash course in Oregon wine culture. In Dundee, the Red Hills Market fuels the expedition with wood-fired pizzas and cases stocked with local artisan finds like Briar Rose Creamery cheeses, Fino in Fondo salumi, and hard-to-find pinot rosés. Head for Worden Road, which ribbons through mossy Oregon woods and sweeping farm-country and mountain vistas, hitting a series of wineries both iconic (Erath, founded in 1967) and upstart (Alexana, founded in 2005 by a doctor/investor from Bangalore). From there, a quick loop on country highways reaches the hamlet of Carlton, where an antique grain elevator towers over a few quiet-but-packed blocks—home to Cana’s Feast and its excellent bocce courts. You might find yourself tempted to pull up stakes for this idyllic swatch of Oregon fertility—then you realize that it’s already right in your backyard.

RAIN PLAN: Skip the vineyards and stick to the tasting rooms, like Argyle’s big barn in Dundee or Scott Paul’s classy brick outpost at the foot of Carlton’s grain elevator.

Float the Clackamas

40 minutes from PDX: Pssst! You don’t have to be 23 anymore to take a ride on the Clack, traditionally known for its rip-roaring party scene. As of last summer, the county banned booze on the water, which means the river is wide open to classy folk like you. Grab your inner tube and put in at the Barton County Park boat launch, just 40 minutes from downtown Portland. The lazy ride to Carver Park takes about four hours—just hold on tight for two brief rapids.

Swim Henry Hagg Lake  

45 minutes from PDX: It may be man-made, but nature has certainly claimed the Scoggins Dam reservoir as her own. The tree-filled park contains more than 13 miles of dog-friendly nature trails and wildlife observation sites for a front-row seat on the lake’s thriving ecosystem—plus a disc golf course, boat ramps and rentals, swimming areas, plenty of rainbow trout for anglers, and party-ready picnic tables and grills for cooking up your catch. On the way home, swing by SakéOne brewery in Forest Grove for a sampling of saké and shochu.