The Columbia River Gorge is one of Oregon's most spectacular landscapes, but just beyond the western crowds lies one of its best-kept secrets. Nestled in the heart of historic downtown, The Dalles blends fascinating history, celebrated wineries, memorable dining, and outdoor adventure—all at a pace that invites you to slow down and stay awhile.

Whether you're planning a romantic weekend, a fall road trip, or a wine country escape, Rayland Hotel is the perfect home base for discovering the eastern Columbia River Gorge.

01 | Discover Oregon's Story

As one of Oregon's oldest communities and a significant stop along the Oregon Trail, The Dalles is where history comes alive.

Wander downtown and discover 33 larger-than-life murals that transform building walls into a visual history of the Columbia River Gorge. From Native American heritage and Lewis & Clark to Oregon Trail pioneers and local legends, each mural tells another chapter of The Dalles' remarkable story.

Continue your journey at Klindt's Booksellers & Stationers, Oregon's oldest continuously operating bookstore, before exploring the Columbia Gorge Discovery Center & Museum. Complete the day with a scenic drive to Maryhill Museum of Art and the iconic Maryhill Stonehenge Memorial.

02 | Savor the Flavors of the Gorge

From exceptional coffee to vineyard lunches and locally crafted beer, The Dalles offers memorable food and drink experiences that are every bit as enjoyable as the scenery.

Start your morning at Caesura Coffeehouse, featuring Proud Mary Coffee, handcrafted espresso drinks, and a relaxed atmosphere that makes it the perfect beginning to a day exploring the Gorge. For lunch, visit La Provence Boulangerie & Patisserie, then head west to Analemma Wines, where estate-grown wines and thoughtfully prepared seasonal cuisine overlook rolling vineyards. End the day with a locally crafted pint at Freebridge Brewing, a favorite gathering place for visitors and locals alike.

03 | Raise a Glass to Columbia Gorge Wine Country

More than 40 wineries stretch from The Dalles to Hood River, offering intimate tasting rooms and spectacular scenery.

Enjoy a glass overlooking the Columbia River at discover boutique producers throughout the Gorge, or simply spend the afternoon exploring one of Oregon's most exciting wine regions. Many of the area's best wineries are within a 30-minute drive of Rayland Hotel.

Enjoy a glass overlooking the Columbia River at  Maryhill Winery, experience estate-grown wines and seasonal culinary offerings at Analemma Wines, or discover the distinctive Rhône-inspired wines of Syncline Winery. From established wineries to small producers, the Gorge offers plenty to explore, with many favorite stops within a 30-minute drive of Rayland Hotel.

04 | Explore the Columbia River Gorge

Drive the Historic Columbia River Highway, take in panoramic views from Rowena Crest, hike at Memaloose State Park, discover waterfalls, or spend the afternoon exploring neighboring Hood River.

Fall transforms the Gorge into a landscape of colorful vineyards, orchards, and crisp blue skies, making every drive unforgettable.

05 | Make Rayland Your Home Base

After a day exploring wineries, museums, scenic overlooks, and downtown shops, return to Rayland Hotel, where thoughtfully renovated guest rooms, warm hospitality, and a walkable downtown location make it easy to experience everything the eastern Columbia River Gorge has to offer.

Whether you're discovering Oregon history, enjoying local wine, or simply taking the scenic route, Rayland offers a welcoming place to relax, recharge, and begin tomorrow's adventure.

Discover the Gorge. Unwind at Rayland.

This fall, explore one of Oregon's oldest communities, sip award-winning wines, discover history, enjoy memorable culinary experiences, and experience the breathtaking beauty of fall in the Columbia River Gorge.

Enter to win a two-night stay at Rayland Hotel and experience one of Oregon's most rewarding fall destinations for yourself.

The next winner will be announced December 15, 2026.

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