Weekend Wonderland: 8 Stops in Oregon from the Mountains to the Vineyards

With these 8 weekend getaways in Oregon, you can head from Portland to an immersive experience in the great outdoors in less than three hours.

The colorful vines lining the hills of J. Wrigley vineyards combat the dark and rainy gloom that embodies Oregon in October. Perched atop one of the larger hills in the Willamette Valley, I have a birds-eye view of the surrounding vineyards and forests from the tasting room’s patio.

During the summer, the area would buzz with tourists and traffic, but today it’s silent. Harvest has come and gone, school is back in session, and the rainy fall weather deters most area oenophiles from venturing out for a day of wine tasting. I have this winery (and seemingly the entire AVA) to myself.

That’s one of the things I love most about Oregon; from Portland, you can drive less than three hours and be among rivers, forests, waterfalls, mountains, vineyards, or coastlines. This accessibility to numerous diverse experiences makes Oregon a weekend warrior’s wonderland.

If you’re looking for some direction, here are eight weekend getaways in Oregon that will make the most of your two days of freedom.


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Small in size yet big in adventure, Bend is a mecca for outdoor enthusiasts. Home to 300 miles of single-track mountain biking trails, 22 golf courses, 15 mountains, 30-plus cascade lakes and 300-plus days of sunshine a year to enjoy the vast outdoor offerings, Bend is a natural playground for families and adventure travelers. Enjoy world-class skiing and snowboarding (at nearby Mount Bachelor) in the winter, or world-class river activities (on the mighty Deschutes River) in the summer months.

After exploring Bend’s nirvana of nature, enjoy some refreshments at one of Bend’s 25-plus craft breweries (or, if you really love beer, taste your way along the Bend Ale Trail). Boasting more breweries per capita than any other city in Oregon, Bend is a bucket-list destination for beer lovers. If you’re visiting, don’t miss the Crux Fermentation Project (great ambiance whether inside or outside), Boneyard Brewery (let the staff indulge you with the backstory), and Deschutes (the brewery that started it all).

End your day with dinner at McMenamins Old St. Francis School (who also brew their own fantastic beer). Known for their atmosphere and sense of community, McMenamins’ restaurants have been a neighborhood gathering spot throughout Oregon and Washington since 1983. Each McMenamins pub is themed to match the neighborhood in which it resides. For instance, Bend’s Old St. Francis School pub serves up Northwest fare (think salmon fillet, truffle fries, and local grass-fed steak and burgers) inside a converted 1936 Catholic school-house with eclectic decor that pays homage to the history of the school and the surrounding community.

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Where to Stay in Bend


The Oxford Hotel is a charming boutique hotel in the heart of downtown Bend, Oregon. That means you’re walking distance to some of the best breweries in the region, so drink up!

The Oxford Hotel

Top rated
9.6 Excellent (821 reviews)
Excellent Cleanliness 9.7 / 10
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Columbia River Gorge

On September 3rd, 2017, Oregonians everywhere watched in horror, despair, and anger as a fire ravaged one of the nation’s most beautiful scenic areas: the Columbia River Gorge. By the end of that Labor Day weekend, the fire claimed 48,000 acres of the most beloved forest in the state, taking with it some of Oregon’s most popular hiking trails, most beautiful landscapes, and most accessible wilderness.

While the Eagle Creek fire caused significant economic, emotional, and environmental damage, the Gorge as a natural wonder was neither lost nor destroyed. Today there are still numerous outdoor recreation options to explore and trails to trek. Those hoping to spend a weekend chasing waterfalls need only cross the historical “Bridge of the Gods” to find beautifully intact hiking trails that boast vista views and waterfalls. Some waterfall hikes that weren’t affected by the fire include Cape Horn Loop, Hamilton Mountain Loop, Panther Creek Falls Hike, and Falls Creek Falls Loop.

The Columbia Gorge is also home to 50-plus vineyards and a growing number of breweries, making it an ideal destination for a weekend of wine or beer tasting (don’t miss Maryhill Winery & Amphitheater). After a day of tasting or trekking around the Gorge, head to Hood River for some farm-fresh dining at Celilo Restaurant and Bar or enjoy a romantic fireside dinner at Multnomah Falls Lodge (located at the base of the famous 620-foot namesake waterfall).

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Hotels in Hood River

332 Hotels
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Where to Stay in the Columbia River Gorge


The Columbia Gorge Hotel is surrounded by beautiful grounds and scenic views complemented by a rich history and friendly staff.

Columbia Gorge Hotel

Top rated
8.6 Excellent (785 reviews)
Excellent Location 9.1 / 10
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Crater Lake

For nature enthusiasts, Oregon’s only national park is an awe-inspiring weekend getaway destination that attracts nearly one million visitors each year. Located in a remote area of Southern Oregon, what Crater Lake National Park lacks in amenities it makes up for in beauty. Though park-goers can take in the stunning scenery while camping, hiking or picnicking, the park’s rim drive is among the most popular pursuits. This route (self-guided in your own car or guided in a trolley tour) provides gorgeous lake views from various angles and perspectives.

With a depth of 1,943 feet, Crater Lake is the deepest lake in the United States and arguably the most beautiful. Surrounded by cliffs (some reaching up to 2,000 feet) the lake is fed entirely by rain and snow, the purity of which gives the lake its intense blue color. In fact, scientists consider Crater Lake to be the clearest and cleanest large body of water in the world.

If you’re visiting, consider bringing fishing gear and catching your own dinner. In addition to crystal clear waters and storybook scenery, Crater Lake also boasts an abundance of rainbow trout and kokanee salmon. And, since the lake contains a million salmon (literally), your odds of catching something are favorable. If you opt to leave the salmon fishing to the bears, your dining options become much more limited as there are only three restaurants in the park. That said, the Crater Lake Lodge dining room is a spectacular place to have a meal while enjoying magnificent lake views (just make sure you get a reservation if you are visiting during the summer).

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Hotels in Crater Lake National Park

3 Hotels
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Where to Stay Near Crater Lake


Overlooking Crater Lake and surrounded by mountains, the historic Crater Lake Lodge is a beautiful home-base for multi-day visitors to Crater Lake National Park.

Crater Lake Lodge

Crater Lake National Park, 3.6 miles to Crater Lake National Park
8.1 Very good (117 reviews)
Excellent Location 9.3 / 10
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What’s the first thing that comes to mind when thinking of Eugene, Oregon? Nike? Probably. Hippies? Maybe. The University of Oregon? Hopefully. However, beneath the town’s celebrated university (go Ducks!) and its famous alums (looking at you, Phil Knight) resides a colorful city crammed with creativity and infused with diversity.

Situated at the junction of Oregon’s Willamette and McKenzie rivers, Eugene may be cumulatively considered a “college town” rooted in the hippie movement and counterculture. However, with a dichotomous mix of arts and culture, sports and outdoors, shopping and dining, and yes, liberal politics and alternative lifestyles, eclectic Eugene is a utopia of arts and adventure (and the activities that naturally follow: eating and drinking).

Like many other cities in Oregon, Eugene is a hotbed for craft breweries. If you love beer, spend some time wandering the Eugene Ale Trail and you may meet your new favorite brew. Ninkasi, ColdFire, and Oakshire are a few can’t-miss breweries in town. For the wine lovers, Eugene also has a great urban wine scene that consists of four-plus winery tasting rooms within a five-mile route between the Whiteaker neighborhood’s fermentation district to the Westside Warehouse district. After tasting your way through town, head down to 6th Street Public Market for a farm-to-table dinner at Marché.

Since a little company called Nike was founded in Eugene, the city has become known as “Tracktown USA” — an epicenter for athletes and repeating host to the U.S. Olympic (track & field) trials. Runners and cyclists love Eugene’s 250 miles of bike and running trails (located right in town), while outdoor enthusiasts enjoy hiking the nearby Spencer’s Butte or Mount Pisgah. With Eugene’s abundance of parks, trees, and trails, anyone wanting to spend some time outdoors will love a weekend getaway to this green city.

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Where to Stay in Eugene


The amenities and attention to detail are both top-notch at this charming boutique hotel, the Inn at the 5th.

Inn At The 5Th

Top rated
9.3 Excellent (906 reviews)
Excellent Service 9.6 / 10
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The Oregon Coast has a rugged, wild beauty that’s unlike any other beach in the nation. Although numerous lovely beach towns fringe Oregon’s 363 miles of coastline, Florence is a local favorite. Situated between the Siuslaw River and miles of sand dunes, Florence, Oregon offers a great getaway for both adventure seekers and relaxation retreaters.

Outdoor enthusiasts flock to Florence for its ample amount of outdoor recreation options. Home to the largest expanse of coastal dunes in the country, adrenaline chasers can bring an ATV, rent a quad or join a Dune Buggy tour to cruise this stretch of sand stacks at a dizzying pace.

On the other hand, if you’re looking for something slightly slower and less adrenaline-inducing, you can ride horses on the beach (with C&M Stables) or take a hike on the scenic trails that surround the historic Heceta Head Lighthouse. The nearby Sea Lion Cave — touted as the largest sea cave in America — is also a favorite among visitors, especially those with their family.

After a day of exploring, head to Old Town for dinner along Florence’s historic waterfront. Plan ahead and make dinner reservations at the Waterfront Depot. Located inside an old train depot, the restaurant serves up creative dishes and beautiful river views.

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Hotels in Florence

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Where to Stay in Florence


Driftwood Shores Resorts is an oceanfront hotel that offers stunning views and easy beach access.

Driftwood Shores Resort And Conference Center

8.0 Very good (1880 reviews)
Excellent Location 8.9 / 10
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Mount Hood

Located 50 miles east of Portland, Mount Hood’s postcard-perfect peak is a dominant point on the city’s skyline and the muse of local photographers and outdoor enthusiasts alike. On a clear day, the snow-capped summit (visible all the way to the Columbia River plateau) beckons adventure seekers to explore its glaciers, forests, and rivers. With year-round opportunities for snow sports (thanks to the aforementioned glaciers) and scenic summer activities (climbing, hiking, camping, kayaking), Mount Hood is an outdoor playground for weekend warriors of all stripes.

Though several small resort towns encircle the mountain, Government Camp (or “Govy”) is among the most popular. Despite being the gateway to several world-class ski resorts, Government Camp — unlike its Canadian (Whistler) and Californian (Mammoth) counterparts — propagates little pretension, but rather provides a warm welcome, and vast après ski offerings to visitors. Ram’s Head Bar, Mt. Hood Brewing Co. and Double Mountain Brewery are all great options for taking a load off, post-ski.

If you’re passing through Government Camp on your way to or from Mount Hood, stop for a hearty meal at the cafe in the iconic Huckleberry Inn. The Inn’s throwback 24/7 diner has been serving up Huckleberry pancakes, shakes and pie (among other diner staples) since 1966.

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Hotels in Government Camp

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Where to Stay Near Mount Hood


At just one mile from the Mount Hood Ski Bowl, you can’t beat this location. Plus, Collins Lake Resort features the perfect combination of luxury and charm to satisfy any traveler.

Collins Lake Resort

Top rated
8.5 Excellent (22 reviews)
Excellent Location 8.9 / 10
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Ah, Portland, a city renowned for rain, beverages, bridges, and hipsters (thanks in part to the hit show Portlandia) is a tapestry of food, wine, beer, culture, art, and outdoor experiences, all woven into one energetic — albeit “weird” — city. Portland, Oregon is a confluence of chaos and creativity, a city as diverse as the people who inhabit it.

In its beautiful mélange, it caters to various types of visitors. Foodie? Portland has one of the best culinary scenes in the country. Craft beer connoisseur? Portland has been called the craft beer capital of the USA. Wine? We’ve got that too. Art? Culture? Outdoors? Yep, Yep and Yep. But I digress.

First things first: brunch. Brunch is something of a religion in Portland, and the city’s breakfast establishments make it an art. If patience is your virtue, Tasty & Alder is renowned for its unique brunch offerings and their innovative dishes are worth the inevitable wait. However, if you’re looking for something on the sweeter side, Voodoo Doughnuts boasts decidedly delicious doughnuts that are sure to satisfy your sweet tooth.

From Voodoo Doughnuts, you can walk across the street to the Portland Saturday Market (the largest continually operated outdoor market in the U.S.) or stroll along the beautiful Portland Waterfront. If you’re visiting during the summer months, there’s a revolving door of events that take place nearly every weekend (many at Tom McCall Waterfront Park), so be sure to do your research and avoid missing out on some of Portland’s most famed festivals (like the annual Oregon Brewers Festival, Portland Rose Festival, or Waterfront Blues festival—to name a few).

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Hotels in Portland

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Where to Stay in Portland


When President Obama visited Portland, he stayed at the Hotel Monaco. If it’s good enough for the Commander-in-Chief, it’s good enough for you.

Kimpton Hotel Monaco Portland

Top rated
Portland, 0.4 miles to Portland Classical Chinese Garden
9.1 Excellent (3606 reviews)
Excellent Service 9.3 / 10
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Willamette Valley

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Known as one of the premier Pinot Noir producing areas in the world, the 150-mile-long Willamette Valley is home to more than 500 wineries. If you like wine (especially pinot), you’ll love spending a weekend in Oregon wine country.

In the Willamette Valley, handcrafted wine takes precedence over corporate, mass-produced labels. Here, large vineyards are complemented by boutique, family-owned wineries and the passion required to succeed in a challenging, cool-climate growing region is evident in every person you encounter and wine you taste.

Boasting beautiful views and great indoor and outdoor wine tasting establishments, Willamette Valley wineries are a year-round destination. The Yamhill-Carlton AVA & Dundee Hills are among the most popular tasting regions due to their close proximity to Portland. If you’re visiting Yamhill-Carlton AVA don’t miss WillaKenzie Estate, Anne Amie Vineyards, Elk Cove Vineyards, Soléna Estate, and Soter. If you go the Dundee Hills route, don’t miss Durant Vineyards, White Rose Estate, Domaine Drouhin, and Domaine Serene.

After a day of wine tasting, indulge in an amazing dinner at the famed Joel Palmer House. Established in 1997 by James Beard award-winning author Jack Czarnecki, the Joel Palmer house restaurant is located inside a historic 1859 farmhouse that was owned by a famous Oregonian by the name of — you guessed it — Joel Palmer. The menu revolves around wild mushrooms and truffles (which they gather themselves) and features seasonal, local cuisine complemented by craft cocktails and an impressive wine list. Pro tip: Try the wild mushroom risotto (even if you don’t like mushrooms, trust me on this one.)

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Where to Stay in the Willamette Valley


Looking for a five-star hotel to match the beauty of the Willamette Valley? Try The Allison Inn & Spa, this luxury accommodation in the heart of Oregon wine country.

Hotel The Allison Inn & Spa

9.6 Excellent (175 reviews)
Excellent Cleanliness 9.5 / 10
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Feature image courtesy of Travel Oregon