July 31—August 2

From prix fixe to Pickathon & beyond

To prep for this weekend’s rustic Happy Valley hoedown (left), treat yourself to a classy dose of Friday fine dining at the sleekly modern Holdfast, which offers a nine-course tasting menu with the kind of exquisite small plates and wine pairings you probably won’t find at Pendarvis Farm’s annual roots music jamboree. Saturday morning, get thee Pickathon-bound and (cowboy boots donned and tent pitched) find a choice spot to lay your blanket near the Mountain View stage, where you can wait for just about everyone you know to amble by. Come nightfall, tick off a show at the fairy-tale Woods Stage, and indulge in some late-night stomping in the Lucky Barn. En route home on Sunday, take a detour by Powell Butte Nature Park for a rousing hike to the summit of this extinct volcano, where, if the day is clearer than your head, you’ll be treated to eye-popping views of Mounts Hood, St. Helens, Adams, and Jefferson. Back in town, slough off that festival grime with a leisurely dip in the Kennedy School’s winningly old-school soaking pool—unless, in your post-Pickathon glow, you’d feel more at home in the clothing-optional bathhouse up the street at Common Ground. 

August 7—9

Head, shoulders, knees, toes

Ease into this high-energy weekend at Pioneer Courthouse Square, where Friday night brings Flicks on the Bricks, an alfresco silver-screen session in Portland’s “living room,” smack-bang in the middle of downtown. (Past highlights include The Princess Bride and a sing-along Grease). Saturday, scoot out into the Gorge and take a frothy ride down the twisting white water of the White Salmon River guided by local outfit River Drifters—then pair a pint with a Cuban pork sandwich on the sun-soaked patio at Everybody’s Brewing in the town of White Salmon. For Sunday, with your arms in full, post-kayak fettle, get your legs up to speed with Bridge Pedal, the annual group spin that lets bikes on Portland’s normally forbidden Fremont and Marquam Bridges. This year there’s the added bonus of putting our newest bridge, Tilikum Crossing, in the mix before its official opening. Reclaim those hard-burned calories at one of the city’s bountiful farmers markets—King Marketoff Alberta Street is a good Sunday bet. Load up your basket, find a spot in the adjacent King School Park, and go horizontal. You’ve earned it. 

August 14—16

The need for speed?

It’s mid-August, people—the office is a ghost town. Knock off early on Friday and slake your thirst at the 11th Annual North American Organic Brewers Festival in Overlook Park. Turn your back on the city below you as you quaff organic brews from your moral high ground at this sustainability-focused fest. Such suds should leave you set for Saturday’s annual adult Soapbox Derby, where otherwise sane individuals hurl themselves down the winding roads of Mount Tabor in garage-crafted vehicles, fueled by gravity and some brand of crazed competition. If you’re not quite up for your own entry, there are ample spots for spectators on the grassy slopes, but claim your spot early: thousands turn out for this annual harebrained hell-raiser. If that sampling of speed whets your appetite for some adventure, Sunday should find you signing up with Willamette Jetboat Excursions for an exhilarating ride along downtown’s riverfront. Still channeling your inner James Bond? Finish up with happy hour cocktails on the roof deck at Departure. Shaken, not stirred, obvs. 

August 21—23

Catch the wind

As the summer sizzles, the waterfront beckons, and you—along with a few thousand of your friends—are invited to the season’s biggest splash-side party. MusicFest NW is adding a Friday show this year, so you can get pumped up with headliners Foster the People, and catch locals Lost Lander before blowing town on Saturday. There’s only one way to recover from a night of beer and boogying in soaring temps, however: a restorative ride down the 20-foot, naturally occurring rock waterslide into the bracing pools of Opal Creek. Sure, you have to drive a couple of hours and hike up a bone-dry road to get there, but a plunge into the sparkling, blue-green river is plenty reward. Invigorated by that baptism? Maybe on Sunday it’s time to take action on those sailing lessons you’ve been talking about for years. Scovare Expeditions offers a 90-minute introduction to sailing on the Willamette, while Portland Sailing Centernavigates the mighty Columbia. As Mark Twain said, “Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.” We totally agree.

August 28—30

Do your own Hood to Coast

If you didn’t snag your spot in the 197-mile relay spectacle that is Hood to Coast, worry not—we’ve got just the DIY journey for you. Start with a trip out to Ramona Falls, not far from the race’s starting point at Timberline Lodge. Given the 1,000-foot climb to get there—complete with a heart-in-throat footbridge crossing—you’ll work just as hard as the runners, but the payoff arrives much sooner: a spectacular, 120-foot-wide cascade that fans magnificently across a basalt backdrop. You’ll have earned your pit stop for a mighty bear claw at Joe’s Donut Shop in Sandy. Hot on the runners’ heels, head for the coast and—a mere 30-minute drive from the Hood to Coast finish line—get your glamp on at Nehalem Bay State Park’s rentable yurts. In the morning, while the hordes are nursing their aching feet in Seaside, hop onto the Oregon Coastal Trail at Tillamook Head for some gut-flipping views as you take in the three-mile loop that swings around Indian Beach. Cap off the weekend with a hearty face-full of fresh Dungeness crab at the classic Bell Buoy of seaside.