Spend a Day in The Dalles

Ditch the rain and head to the growing city on the Columbia River.

The Dalles Oregon Winter 2024, Chase the Rain Shadow (portofthedalles.gov)

Even those folks who have lived in our fair Portland for their entire lives get fed up with the rain. The constant wet for days on end can quickly start to feel oppressive, especially during these days when the sun disappears by 5 pm each night. Sure, the ideal solution is to hop a plane for a sunnier clime—but maybe there’s not time for an extended trip, or budget for a plane ticket. But if you’ve got a day to spare, consider a closer adventure: head east to the other side of the Cascade Range.

It’s there that residents of Central and Eastern Oregon get to experience the benefits of the rain shadow effect, a meteorological phenomenon in which the windward side of mountains absorbs most of the precipitation, breaking up clouds, and causing warmer air to flow down the leeward side. In other words, winters tend to be drier, sunnier and a lot more pleasant than what we suffer through here in Portland.

The only question remains: Where does one go in their quest for better weather? Though you may have whizzed past it many times on your journey along Interstate 84, The Dalles should be your next destination. The largest city in Wasco County is well known among wine enthusiasts, but proud locals are working hard to put their hometown on the cultural map. As you’ll see ahead, their efforts have yielded some impressive results.

Here are a few things we suggest you do in The Dalles this winter:

Take In Some Historic Views

A great first stop on your journey into The Dalles is the Columbia Gorge Discovery Center & Museum (5000 Discovery Drive, 541-296-8600, gorgediscovery.org). Not only is it one of the first exits into town off I-84 east, but it is also a gold mine of information and history about how the city came to be. The center’s exhibits allow visitors to follow a vast timeline starting way back in the Ice Age and carrying through to the early ‘00s. The curators do a fine job highlighting the legacy of the Wasco and Wishram peoples that once thrived there via displays of their crafts and tools, even as they elide some of the uglier chapters of the story covering their forced removal from their homeland. Other surprises in the museum are a sheet tallying the votes in the 1984 primary election when the county voted overwhelmingly for Jesse Jackson and copies of the in-house newspaper of Rajneeshpuram, the religious community that wreaked havoc in Wasco County in the ‘80s.

Columbia Gorge Discovery Center & Museum, The Dalles Oregon Winter 2024, Chase the Rain Shadow (National Park Services)

An added benefit to your stop is that the center sits near the head of The Dalles Riverfront Trail (gorgefriends.org/hike-the-gorge/the-dalles-riverfront-trail.html), a 6½-mile path perfect for biking and hiking that takes you along a beautiful stretch of the Columbia and past a camp used by Lewis and Clark on their westward journey, natural coves and, well, a Google data center. Take the whole ride and you’ll land at Riverfront Park where a lovely beach awaits you. Maybe not the best time of year for wading or swimming, but who could say no to a nice lounge in the sand?

Shop Local on 2nd Street

If you’re one of those forward-thinking types that looks at a day trip as an opportunity to knock another item off your to-do list, like, say, gift shopping (maybe for the holiday season, depending on when you grab this magazine), The Dalles has you covered. The humble downtown area has plenty of shops and spaces with all sorts of potential presents to choose from. If, for example, you wanna get crafty with it, book some time at The Workshop (116 E 2nd St., 541-300-8088, thedallesworkshop.com). This cozy spot has a wonderful market packed with items made by local craftspeople. If you want to get hands on, there are crafting tables and classes so you can whip up something special for that special someone on site. And their selection of beer and wine will help any little mistakes you make a lot easier to bear.

Lines of Design, The Dalles Oregon Winter 2024, Chase the Rain Shadow (Courtesy of Lines of Design)

The Dalles is also home to Klindt’s Booksellers (315 E 2nd St., 541-296-3355, klindtsbooks.com), the oldest bookshop in the state. Opened in 1870, the business is a little slice of history with the original flooring and much of the original shelving still in use. The book selection is top notch, with especially great sections on Native American subjects and local flora and fauna, as is the array of cards, paper goods and kitschy items for the bibliophile in your life. The real treasure, though, is the backroom devoted to kids’ books. It’s colorful, inviting, and just the place to inspire a lifelong love of reading.

Other great options for your gift search are Yesterday & Today Music (414 E 2nd St., 541-296-1441), the lone record shop supplying the town with new and used vinyl and CDs; Urban Paper (415 E 2nd St., 541-298-2767), a great spot to snap up craft supplies or holiday cards; and Lines of Designs (107 E 2nd St., 541-296-4470, linesofdesigns.com), a long-standing boutique with fashions for women of all shapes and sizes.

The Workshop, The Dalles Oregon Winter 2024, Chase the Rain Shadow (Courtesy of The Workshop)

Taste The Dalles

The wineries in The Dalles maintain a constant presence, with tastings happening year-round and many busting out potbelly stoves so visitors can still sip outside. Your options on this front are many and varied. The tasting room at Tierra De Lobos Winery (201 Osprey Lane W, 541-769-0277, tierradelobos.com) offers gorgeous views of the Columbia River and The Dalles Dam along with generous pours of its signature whites and rosés. 15 Mile Winery (623 E 2nd St., 541-965-1445, 15milewinery.com), meanwhile, runs the gamut from sweet dessert wines to hearty pinot noirs, which you can sample during the tasting room’s weekend hours.

Bargeway Pub, The Dalles Oregon Winter 2024, Chase the Rain Shadow (Courtesy of Bargeway Pub)

But if you only have time for one stop, head right to Quenett Winery’s Sunshine Mill (901 E 2nd St., 541-978-9588, sunshinemill.com) if only to get a glimpse a bit of The Dalles history. The tasting room and hangout spot has a steampunk vibe as it retained much of the machinery that once milled tons of wheat for the Sunshine Biscuit Company, creators of Krispy crackers and those little bits of heaven known as Cheez-Its. But into the space it’s built a lovely restaurant and tasting room, complete with plentiful outdoor seating and a bocce court.

For beer lovers, some of the best quaffing can be done at Freebridge Brewing (710 E 2nd St., 541-769-1234, freebridgebrewing.com). The website says it specializes in German lagers and Northwest ales, but the menu of craft beers goes well beyond that to include a delicious amber and the award-winning Slap & Pickle Gose, a sour made with pickle juice that drinks surprisingly easy in spite of its inherent tartness. For a wider array of beer options, consider Bargeway Pub (1535 Bargeway Road, 541-370-2345, bargewaypub.com), an oft-bustling spot with an impressive menu of regional cuisine and pub standards. It’s also a hub for Little Music City, a local network of musicians and music lovers looking to raise the profile of the local community. The group has a standing rotation of local artists playing around town with designs on bringing in acts from Portland and beyond. Stop by the Bargeway every Sunday to get a taste of the sounds they’re offering up.


This story is a part of Oregon Winter, Willamette Week’s annual winter activity magazine. It is free and can be found all over Portland beginning Friday, December 13, 2024. Find your free copy at one of the locations noted here or at our online store, before they all get picked up!

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