Summit Silver Star Mountain 

90 minutes from PDX: A clear day on Silver Star Mountain’s peak offers perhaps the most spectacular view within a day’s trip from Portland: St. Helens, Rainier, Adams, Hood, and the Gorge seem to radiate from your very own vertex. There are three main approaches: Grouse Vista Trail from the south (easiest drive, steepest hike), Silver Star Trail #180 from the north (easiest hike), and Bluff Mountain Trail from the east (longest drive, most stunning views). Bluff Mountain traverses mostly bare ridges of bear grass and wildflowers (trees never recovered from the Yacolt Burn of 1902), providing rare unencumbered views. Leave dinner and beers in a cooler at the trailhead for a sunset picnic overlooking Adams and Hood.

Rafting & Fishing in Maupin 

2 hours from PDX: If it weren’t for the lively Deschutes River carving through this little high-desert outpost, Maupin might be the sunny home of just a few lonely ranchers. Instead, it’s a hotbed of river rats and ambitious anglers. Book a journey with Deschutes River Adventures and paddle 13 miles through the desert canyon filled with sagebrush, osprey, surreal basalt formations, and plenty of white water. Or stick closer to the shore with a fishing rod and cast for epic runs of salmon and steelhead. Charmed by Maupin? Shack up at the Imperial River Company on the banks of the Deschutes, which also offers guided rafting and hunting trips.

Saddle Mountain & Cannon Beach →

90 minutes from PDX: Why choose between mountains and ocean? Saddle Mountain offers a 360-degree panorama of both the Cascades and the Pacific at its rewarding summit, atop 5.2 miles of forested switchbacks and steep meadows of summer wildflowers. Appetite well earned, tuck in at the Irish Table in Cannon Beach, where flickering candles and ramshackle wooden décor transport you to a stormy sea shanty. Don’t miss the generous piles of fresh crab heaped on toast, or the seared flatiron steaming in a Jameson peppercorn sauce. End your day with the best digestif of all: sunset on the beach.

RAIN PLAN: Skip the hike and head straight for Sleepy Monk Coffee Roasters in Cannon Beach for a soothing brew. Brave a brisk walk on the beach before returning to town for dinner—the Irish Table is most romantic in a squall.

Summer Skiing on Mount Hood 

90 minutes from PDX: For solid summer snow, wake up with the sun and point your wheels toward Timberline’s Palmer Snowfield. On the way, grab yourself a maple bacon bar from Joe’s Doughnuts in Sandy. Start by playing in the soft snow below Magic Mile. Around noon, catch the Palmer chair as the ski racers pack up from their morning runs. Up top, savor the views of Mount Jefferson, the Three Sisters, and the Salmon River before carving through acres of open snow on the west side of the glacier. For a new après-ski tradition, dip your burning quads in Trillium Lake while gazing up at your tracks, and reward yourself with a feast of mac and cheese at Skyway Grill on the way home.

Oysters in Long Beach 

2.5 hours from PDX: Jutting between the Pacific Ocean, the Columbia River, and Willapa Bay, the 28-mile Long Beach Peninsula is a dramatic spit of picturesque sand dotted with nature havens and small towns. Shortly after traversing the Astoria-Megler Bridge, you’ll find a hearty dose of fresh air at Cape Disappointment State Park, where coastal old-growth forests, bunkers of an old military fort, and the pocket-size driftwood fantasyland of Waikiki Beach provide your playground. Continue north through Long Beach to the Nahcotta Tidelands Interpretive Site, where you can gather and shuck your own Pacific oysters from the beds of Willapa Bay.

Stevenson & Carson, Washington  

1 hour from PDX: Your four-point plan for loving the Gorge’s chill northern side:

1. Head first for a quick hike around Stevenson, where Norman Rockwell Americana gets upgraded with ample brewpubs and ballistic river sports. 
2. Scope out the charming microdowntown, home to a select few spruced-up boutiques (example: Out on a Limb, for “home + her”) and mainstay local favorites like Big River Grill and Walking Man Brewing.
3. Amble (and scramble) the riverfront paths, parks, and dusty access roads to a chain of semihidden rocky beaches, gust-blasted windsurfing and kiteboarding launch pads, and secluded spits for fishing or just contemplating the Columbia River’s essential awesomeness.
4. Conclude in even-tinier Carson, just down the road, where microbreweries are popping up like mushrooms. A turn up a country lane leads to Acadian Farms. You may think you’re hallucinating, but it’s real: a gorgeous rolling field, populated by bleating goats, holds a tiny brewery in a shack with a corrugated roof. The saison, served in a pint mason jar, is terrific. 

Bonus: Stay the night! The tried-and-true option would be Skamania Lodge, Stevenson’s tribute to WPA-style woodsy splendor. Farther afield, the Inn of the White Salmon offers both modernist rooms and hostel beds. 

Get Sporty 

ZIP-LINING: Located 90 miles from Portland just past Astoria, Highlife Adventures offers a “tour” through eight lines that crisscross a small lake, adding up to more than a mile of aerial travel for $99. Believe us: zip-lining never gets old. 

KITEBOARD LESSONS: Jealous of those kiteboarders blowing in the air? Head to Cascade Kiteboarding in Hood River, where private or two-person lessons get you out riding the Gorge gusts. The thrilling 2.5-hour sessions start at $275.

FLYING LESSONS: Unnerving as it may be, this is a fact: you don’t need a pilot’s license to fly a plane. Aurora-based Willamette Aviation offers “discovery flights” for first-time pilots for $150, pairing you with an instructor who’ll help you taxi, take off, and land a Cessna 172. 

HANG GLIDING: Another way to get air? The family-friendly Oregon Hang Gliding School, with locations in Corvallis and Pacific City, offers full-day lessons to anyone who can “jog-run.” You won’t be jumping off any mountaintops, but the $130 course will let you soar off of 7–12 manageable perches, moving higher and higher as you gain experience and comfort.