Just 60 miles east of Portland, perched on the Columbia River Gorge, is Hood River, a town acclaimed equally for its quirky charm and rugged sensibilities. It’s famed as the capital of windsurfing, but rumor has it the shopping and dining scenes rival the big city. It’s an easy and scenic drive out, so a friend and I decide to investigate with a weekend escape and a little retail therapy.

Heading out on I-84, we’re soon flanked by the sparkling blue expanse of the Columbia River on our left and the lofty, jagged gorge cliffs dotted by old-growth trees on our right. Near Troutdale, we abandon the freeway and veer right onto the Historic Columbia River Highway.

Dubbed “king of roads” and now a nationally designated All-American Road, this route has the full spectrum of emerald hues. The road goes on for miles, speckled with waterfalls and accented with majestic trees and mossy stone walls. Some falls are easily viewed from the road, while others are accessible by treading forested trails. We’re eager to hit a few stores in Hood River before it gets late, so we choose Oregon’s largest waterfall to inspect up close—Multnomah Falls. The payoff is grand, and we’re refreshed for the rest of our drive.

We arrive and park the car for the weekend. With hotels, restaurants and shops located within a six-block radius, everything is walkable here.

Hood River is much more than the small agricultural outpost founded over a century ago. It is still the capstone of the route known by locals as the fruit loop, with more than 14,000 acres of commercial orchards blooming in the area. But where there once were fruit-packing companies in the downtown district, there are now chic boutiques and art galleries inhabiting the early-century industrial spaces. Some have even kept the old packing equipment intact, preserving them as shop fixtures.

Oak Street, the main drag, feels like a Hollywood movie set with its brick-faced facades and glittering white lights. Holiday gift getting is easy: shops retail everything from hip clothing and one-of-a-kind jewelry, antiques that range from French provincial to farmhouse, plus ceramics, cookware, home décor, stationery, fantastic book selections and more. By sundown we are laden with goods and have worked up quite an appetite.

We make a pit stop at the historic Hood River Hotel, our home base for the weekend. The refurbished 1911 building was updated with modern amenities but retains its vintage charm. I can’t wait to soak in the hot tub and rest my weary bones in the four-poster bed, but first—dinner.

At Nora’s Table, we reward ourselves with a shared feast of lots of small plates and an entree of Oregon black cod and pears. A minimalist aesthetic, with exposed wood beams and poured concrete floors, complements the distinctly local menu.

After dinner we meander back to the hotel, negotiating the can’t-miss activities we will explore tomorrow, hoping we can stretch the hours of this weekend just a little longer.

This Itinerary includes one of Oregon’s Seven Wonders. See one, or better yet, see them all!

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These maps and directions are for planning purposes only. You may find that construction projects, traffic, or other events may cause road conditions to differ from the map results. For travel options, weather and road conditions, visit tripcheck.com, call 511 (in Oregon only), 800.977.6368 or 503.588.2941.

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