The Columbia Gorge's Best-Kept Secret Is A Sun-Drenched Town With Wineries, Music & Scenic Trails

Just 80 miles east of Portland along the I-84 E, in the shadow of the towering Mount Hood, lies the City of The Dalles, an underrated destination that offers visitors the chance to experience Oregon's thriving culture as well as the area's outstanding natural beauty. Though the area can become very cold and snowy in the winter, The Dalles' long, comfortable summers make it the perfect place to unwind and connect with the natural world.

The city itself has a population of around 16,000 (as of 2023), but while it is small when compared to neighboring Portland, it has a bustling culture all its own. There's enough wine, music, art, and history to keep visitors entertained for days on end. Combined with numerous nearby beauty spots and easily accessible biking and hiking trails, The Dalles offers a well-rounded experience perfect for those looking for a vacation with a little bit of everything.

The Willamette Valley may be the Oregon wine region of choice for those in the know, but The Dalles has its own thriving wine scene with more than 30 wineries in the area. Locals know it as the Columbia Gorge. With its long growing season, it is quickly becoming known as an up-and-coming wine region. Not that wine growing in the region is new: The Sunshine Mill Artisan Plaza and Winery has been operating in The Dalles for over a century, producing some of the finest Pinot Noir and Viognier.

The bars of The Dalles aren't just a hub to enjoy a glass of the area's delicious wine (among other beverages). They also offer some of the best points of entry to local culture. Downtown is known for its music scene, with musicians performing in local bars almost every night. The waterfront Bargeway Pub is especially highly rated, with outdoor concerts taking place against the stunning backdrop of the Columbia River. There are also frequent outdoor performances at places such as The Dalles Art Center, which also serves as an exhibition space.

Other can't-miss attractions include the Columbia Gorge Discovery Center & Museum, a 54-acre riverfront site that covers 11,000 years of Oregon history, including the Lewis and Clark Trail and the Oregon Trail. There is also a theater on-site, as well as the Columbia River Trading Co., which focuses on local arts and crafts. Visit the city in April to attend the famous Northwest Cherry Festival and celebrate the area's production of sweet cherries with a parade, live music, a market, and family-friendly activities.

The Dalles experiences a good deal less rain than other parts of Oregon, making it ideal for daylong outdoor recreation. For hikers, the area offers plenty of scenic routes, including a moderate 90-minute loop through the gorgeous Memaloose Hills. For great views of the city itself as well as nearby Mount Hood, you could take the 3.2-mile Eagles Caves, Rim, and Lower Bench Loop, which is lined with beautiful wildflowers during spring and summer.

However, many visitors now choose to explore Columbia Gorge by bike. Many of the routes used by hikers are also cyclable, as is the Historic Columbia River Highway, the country's oldest scenic route that runs between The Dalles and Troutdale. There are a total of 25 biking routes around The Dalles, including a circular, family-friendly 10.6-mile Riverfront Trail to the Columbia Gorge Discovery Center. Routes are equipped with amenities like stations to help with flat tires. Along with views of the river and mountains, you will encounter waterfalls, scenic plateaus, lookout points, and places to stop, eat, and rest. The 34-mile Mosier Loop represents the biggest challenge to cyclists in the area, with nearly 3,000 feet of elevation taking you to Rowena Crest Viewpoint, with unbeatable views in all directions.

Looking for some relaxation time? About an hour west of The Dalles, across the state border, awaits a historic hot springs resort tucked away on Washington's side of the Columbia River Gorge.