Do you know a great time for Oregon weekend getaways? Anytime. Do you know the best time for weekend getaways in Oregon? Right now!

While concerns about rainy weather on a visit to Oregon are understandable—if somewhat overblown—there is a definite seasonality to the area’s precipitation. Getting wet is pretty easy in the fall and winter, but summer is typically warm and dry. And with the state’s mild temperatures and far-from-overheated tourist profile, you’re unlikely to get scorched by the sun or burned by exorbitant prices while enjoying getaways in Oregon—whether in summertime or any other time of year.

My husband Mike and I recently returned from a couple wonderful visits to the Beaver State. After our amazing road trip from San Francisco to San Diego earlier this year, it was time to explore more of America’s wonderful West Coast. We had a blast!

We found some unique places to stay in Oregon, including a few of the best places to stay along the Oregon Coast. We went with some great Oregon vacation ideas, and picked up plenty more along the way.

We travelled from Astoria and Seaside, near Oregon’s northwestern coastal tip, down to Brookings, its southwestern coastal tail. We visited Portland, the state’s culinary capital, and ventured further inland to tap into the allure of Hood River and the Columbia River Gorge. We also checked out Ashland, where things are known to get quite theatrical.

As you can imagine, we found some delightful places to eat and drink. We also enjoyed some highly entertaining and engaging activities that didn’t require a fork or glass.

Now, I’m eager to share with you some tips for great Oregon weekend trips for foodies. Whether you’re looking for romantic getaways on the Oregon Coast, outdoor activities amid natural wonders, or some of the best weekend getaways in Oregon for culture, our recommendations will make sure that you eat well, no matter what else you choose to do! Let’s explore!

Astoria

The charming city of Astoria makes for a perfect weekend getaway in Oregon. In fact, its location less than a 2-hour drive from Portland makes Astoria one of the best weekend getaways from Portland, or a great side-trip for anyone visiting Portland.

Situated at the mouth of the Columbia River, just east of where the river meets the Pacific Ocean, Astoria is the oldest U.S. settlement west of the Rocky Mountains. The city nestles the bank of the river and spreads high into the hills above.

The vibrant downtown commercial district starts along the water’s edge then gives way to the mix of colorful homes whose mosaic forms a haphazard rainbow as they climb higher and higher from the city center. But beautiful scenery is merely one of the features that attracts visitors to Astoria.

Astoria Riverwalk — Astoria Column in the hills high above the Riverwalk

Where To Stay in Astoria—Bowline Hotel

My husband Mike and I recently stayed at the Bowline Hotel. Trust me when I tell you, it’s got to be one of the most unique places to stay in Oregon.

It’s located on a dock that juts out into the Columbia River. At the Bowline, you’re not staying close to the river or river adjacent—you are ON the river. When a boat or ship goes by, the wake it makes will ripple under the dock and you will hear the water beneath your room swish and splash as a result.

Astoria-Megler Bridge at night from the deck outside our room at the Bowline — Astoria-Megler Bridge at night, from the deck outside our room at the Bowline

And since the Columbia River is so integral to Astoria, I can’t imagine a better place in town to feel its pulse. Be sure to get a river view room. These look right out onto the Columbia, with vistas of the Astoria-Megler Bridge that connects to Washington, and the verdant tree-clad hills that rise up from the shore on the Washington side of the river.

The rooms are large, with a fitting nautically industrial theme, and feature a fireplace inside and private deck outside. We spent a lot of time on the deck taking in all the sights. Among them were sea lions, seals, herons, and cormorants, to name just a few. It got to the point where, even at night, in the dark, we could recognize the sound of a sea lion breaking the surface of the river and coming up for its first breath since submerging. Amazing!

weekend getaway at the Bowline hotel in Astoria — Our room at the Bowline Hotel in Astoria, one of the most unique places to stay in Oregon

The Bowline is not only uniquely located on the water, but conveniently located on the Riverwalk, the almost 13-mile waterfront walkway and bikeway that snakes along the Astoria shore. The hotel’s central location is literally steps away from the historic downtown. Since hotel guests are provided with complimentary bike rentals, exploring the town and surrounding area by foot or bike is easy, free, and fun.

The Bowline also boasts its own bar, the Knot, which serves delicious drinks and eats with a view. Guests can also enjoy private views from the hotel’s saunas, which overlook the Columbia River.

With its location right on the water with private decks providing intimate views of the Columbia, and rooms brightened by the sunshine bouncing off the river or bathed in the glow of a flickering fireplace, the Bowline is surely one of the most romantic places to stay in Oregon. But there are plenty of things in Astoria to coax you out of your room as well.

Thank you to the Bowline Hotel for helping to sponsor this post!

View of the Columbia River — The Knot Bar’s gorgeous Columbia River view

What To Eat and Drink in Astoria

For a city of 10,000 people, Astoria offers a surprisingly rich variety of inviting eateries and drinkeries. Among other things, Astoria is definitely a great beer town. Six of the 14 breweries or pubs included on Oregon’s North Coast Craft Beer Trail make their home in Astoria. Most are housed in historic buildings, including two of my favorite choices:

Buoy Beer Company Located nextdoor to the Bowline Hotel, this brewery and restaurant occupies a former cannery right on the Columbia River and offers tasty brews and bites with a great view. I loved all the beers I tried, and the clam chowder at Buoy is one of the best I’ve ever had, right up there with my all-time favorite—my grandma’s.

Clam Chowder and Fish and Chips at the Buoy Brewery

Fort George Brewery Starting as a single brewpub, Fort George has expanded to occupy an entire city block. It now features multiple restaurants, tasting rooms, breweries, community spaces, and live music venues. If you can’t find the beer, food, or views you want from all the options offered here—you’re not really trying.

But beer-centric eateries are far from the only good spots to enjoy fine food in Astoria. While in town, I had some memorable meals in traditional brick-and-mortar settings, from a food truck, even off an old boat. Here are some that I can confidently recommend:

Blue Scorcher Bakery and Café Even if you didn’t know the selection of vegetarian breakfast options available here were delicious, you’d be drawn in by the alluring scents of baked goods and roasting coffee wafting out the front door as you pass by. The more substantial egg-centric meals are complemented by a variety of breakfast pastries and breads, all made from scratch and as pleasing to the eye as to the palate.

Fresh baked bread makes any weekend getaway better — The bread display at Blue Scorcher Bakery and Café

Pig ‘N Pancake Going strong since 1967, this restaurant is loaded with locals at breakfast. Plates arrive with generous portions of old-school favorites done right. The tasty food is served up in a wonderfully authentic small-town atmosphere, with diners often stopping by other tables to catch up on the latest with friends or hugging a favorite server on the way out.

Bowpicker Fish & Chips A retired fishing boat outfitted with fryers and a walk-up window offers a no-frills, great-taste seafood staple: Fried beer-battered albacore tuna on a bed of steak fries. You must pay with cash only and can enjoy your order at some picnic tables across the street or half a block down from the boat.

Fish and chips at Bowpicker are a must on a weekend getaway to Astoria — Bowpicker Fish and Chips are a must on your weekend in Astoria, Oregon.

Carruthers With its elegant interior in an attractive historical building, Carruthers offers a tasty mix of well-made American favorites and creations from further afield. A lovely bar also serves up creative cocktails with flair. Carruthers’ location is also great, right in the heart of downtown.

Sasquatch Sandwich Shop This food truck offers up hearty helpings of inventive sandwich riffs. Mike and I thought the Korean BBQ Pork on Sourdough and the Korean Reuben sounded particularly interesting, so we shared them. Outstanding!!! If I lived here, I’d work my way through the entire menu in a fortnight!

Humongous and mouthwatering Sasquatch sandwiches

Things To Do in Astoria When You’re Not Eating

Like its dining scene, Astoria’s doing scene is more diverse than you would guess from its size alone. For history buffs, options include climbing the 164 stairs of the Astoria Column. The column celebrates the discovery of the Columbia River, Astoria’s founding, and the conclusion of the Lewis and Clark Expedition. The observation deck offers commanding views of the city and surrounding countryside.

Fort Clatsop is a replica of the fort built by Lewis and Clark on their expedition to explore the vast territory that the United States acquired in the Louisiana Purchase. The fort is part of the sprawling Lewis and Clark National Park, which offers miles of trails in addition to its museum and Fort Clatsop.

The Columbia River Maritime Museum offers a comprehensive look at the history of navigation on the Columbia—a perilous but critical Pacific Northwest shipping artery. Exhibits and artifacts also tell the story of the nearby Pacific and neighboring waterways within the region.

Heron wading in the Columbia River — A Great Blue Heron wades in the Columbia River.

The Oregon Film Museum is housed in the old Clatsop County Jail and pays homage to the history of movie productions in the state. “The Goonies,” “Short Circuit,” and the “Free Willy” movies are just a few of the flicks filmed in Astoria.

The Astoria Riverfront Trolley offers rides with an informative talk about the town for $1 along a 3-mile stretch of the old freight railway tracks that line the Columbia River.

Astoria is known for the Victorian homes that still grace its hills. The Flavel House Museum offers tours of one of these architectural beauties. The lesser-known George and Lilla Sanborn Home is another gorgeous example worth exploring.

The Flavel House Museum is an example of the Victorian architecture in Astoria, Oregon.

Seaside

The town of Seaside was Oregon’s first seashore resort community, attracting visitors as far back as the 1870s. It remains a popular destination today, drawing beach enthusiasts from far and wide to this idyllic stretch of the Northern Oregon coast.

Its wholesome, old-school feel makes it a family favorite, with many visitors continuing the generations-old tradition of Seasiding within their own family. But as newcomers, we too enjoyed the wide, flat beaches, natural beauty, and savory seafood spots Seaside has to offer.

The gorgeous Oregon Coast, just south of Seaside

Where To Stay in Seaside—Ashore Hotel

Like the Bowline Hotel in Astoria, the Ashore Hotel in Seaside is part of the Adrift Hospitality group. And Adrift Hospitality has a knack for choosing great locations in appealing destinations. Ashore is just steps away from the Seaside Promenade—the 1.5-mile paved walkway along the beachfront—and less than a block from Broadway Street, the town’s epicenter of shops, restaurants, bars, and cafes.

Guest rooms have a Scandi industrial vibe, with most boasting their own fireplace, and each sporting a flat-screen TV, fridge, and French-press setup complete with locally crafted coffee. There’s a small indoor pool and sauna, and an outdoor communal cubby corner with fire pit.

Warm, cozy robes at Ashore Hotel in Seaside, Oregon

The hotel bar accommodates thirsts of all kinds, serving cocktails, a nice selection of local beers and wines, and a wide variety of coffees and teas. Eats include breakfast options in the morning, and then paninis, salads, snacks, and boards until closing. We enjoyed the impressive “Everything Board” one night—a bountiful collection of charcuterie, cheeses, breads, spreads, and assorted olives and pickles.

The hotel-provided complimentary cruisers were great for taking a spin on the Promenade and pedaling along the beach before sunset. Staff was very welcoming, and fellow guests were friendly. Ashore’s great location, ample on-site amenities, and comfortable room made for a satisfying stay.

Thank you to Ashore Hotel for helping sponsor this post!

The “Everything Board” and some cold beers at the Ashore Hotel Bar in Seaside, Oregon

Where To Eat and Drink in Seaside

Wherever I go, I try to eat the cuisine that predominates in the area I’m visiting. In Seaside, situated right on the Pacific, it’s not surprising that seafood is the catch of the day—everyday. So, Mike and I ate a lot of fresh seafood and tested our hunch that since Buoy had such good clam chowder in Astoria, we should be on the lookout for more of the good stuff while on the coast.

Dooger’s Seafood and Grill Following a tip from a friend who had just visited Seaside days before we arrived, we checked out Dooger’s for their clam chowder. The tip was solid: The chowder was rich and creamy, with plenty of clam and not too much potato. The Fish & Chips were also a hit: fresh, flaky fish, not too much batter, and splendid sweet potato fries. And marionberries are big in Oregon, so, of course, we had to try the Marionberry Cobbler. Yay! Let’s just say, we had some return engagements at Dooger’s while in town.

Fish & Chips with Sweet Potato Fries and Cole Slaw at Dooger’s in Seaside, Oregon

Nonni’s Italian Bistro You don’t have to eat seafood at every meal in Seaside—but you can. Even at this cozy, family-owned restaurant focused on bringing the owner’s Italian grandma’s (or Nonni’s) recipes to your table, Cioppino and Seafood Pasta features on the menu. But there’s also plenty of Italian landlubber favorites too. Fresh pastas, scratch sauces, and abundant choices bring the flavors of Italy to the Oregon coast. And a complimentary Sambuca or Amaretto comes with dessert.

Norma’s Seafood and Steak Norma’s has been pleasing Seasiders and visitors alike since opening their doors back in 1976. With an extensive menu of seafood favorites (including their clam chowder, chosen as one of America’s Top 10 Soups by Epicurious) and a wide range of surf and turf options, you’re bound to eat well here. We tried the chowder and a big mound of steamer clams for lunch one day: Both were big hits!

Steamer clams and clam chowder make for a delightful lunch at Norma’s in Seaside.

Finn’s Fish House Razor clams are an Oregon Coast specialty, and Finn’s does a fine grilled version with a tasty dill aioli. The pan-seared scallops were also cooked just right. Many more seafood choices are also available. In addition, there are prime rib, rib eye, and numerous burger options for the beef-inclined. The spacious deck is perfect for al fresco dining, and the lounge offers plenty of signature cocktails to sip indoors or out.

Osprey Café Owned by an avid global traveler, Osprey brings an international flair to a menu that makes room for plenty American favorites. Arepas, chilaquiles, and an Indonesian shrimp, chicken, and rice Nasi Goreng were among the unexpected offerings at breakfast. I really enjoyed the arepas, and Mike gave a thumbs-up to the Eggs Benedict as we enjoyed our morning meal at an outside table, serenaded by the sounds of waves crashing and seagulls cawing nearby.

Arepas with eggs and black beans — Arepas breakfast plate at Osprey Café

Things To Do in Seaside When You’re Not Eating

With its beautiful beach, it’s little surprise that Seaside is the perfect place to sink your feet in the sand, make your way out to the waves, swim until you tire, rest, and repeat. Breathing in the sea air, feeling the sun and salty sea spray on your face, looking far out onto the watery horizon—all melts your cares away and makes for one of the best weekend getaways from the workaday world.

Family fun can be had at the Seaside Aquarium, one of the oldest aquariums on the West Coast. Children can explore the touch tanks that house anemones, sea stars, and sea urchins. Visitors can also feed the resident seals. Nearby, Funland Arcade features dozens of games that offer tons of entertainment in addition to go-karts and bumper cars.

Outdoor enthusiasts will enjoy Ecola State Park, a mere 20-minute drive from Seaside. Miles of trails both thread the spruce forest and cling to coastal cliffs. Scenery switches from towering trees to jaw-dropping views of the Pacific, with giant boulders known as sea stacks dotting the surf below. The park’s a great spot for wildlife viewing as well. Deer, elk, and eagles populate the park year round, while whale watching is possible in the winter and spring when gray whales migrate offshore.

Sea stacks off the coast of Ecola State Park, near Seaside, Oregon

Portland

For more than a decade, Portland has been a regular on US Foodie City Top-10 lists, even being tapped as #1 from time to time. That’s reason enough to earn a spot on any Oregon getaways list. But the country’s culinary crown is just one of the hats that Portland wears, and there are plenty more aspects to the city that make it worth exploring on at least one of your weekend trips in Oregon.

Where To Stay in Portland—Hyatt Centric Downtown Portland

Location is a key element in selecting lodging for any trip, but for city travel, a central location is a must. Portland is Oregon’s biggest city, and there is tons to do there, but never enough time to do it all. So, picking a hotel in the thick of things is your best bet for doing as much as you can in the time that you have. In Portland, the Hyatt Centric Downtown Portland is a great pick! In my opinion, it’s located in the best area in which to stay in Portland.

In the heart of downtown and just steps away from the Pearl District—Portland’s capital of chic, home to art galleries, stylish boutiques, and acclaimed eateries—the Hyatt Centric is ideally situated. Especially for someone like myself, who loves to walk as much as possible in a city to try to get the real feel of it, the Hyatt Centric is definitely one of the best places to stay in Portland, Oregon. Most of what we did during our recent stay was within walking distance or a short Uber ride away.

The Hyatt Centric opened in 2020, sports an appealing modern design, and looks stylish throughout. Our lovely high-floor corner room had a smart, comfortable layout and a completely unexpected but highly appreciated perk: views of two snow-capped mountains rising high above the vibrant cityscape laid out beyond our windows!

And as you might know by now, I love a hotel with a great breakfast so that I can get an early start and a delicious meal first thing in the morning. The Dining Room delivered on both counts with an amazing avocado toast. At the other end of the day, the Dining Room bar served up great nightcaps before we made our way up to the room at the close of our evenings. It’s nice to stay in a hotel that’s got your back, no matter the time of day.

Thank you to the Hyatt Centric Downtown Portland for helping to sponsor this post!

Avocado Toast at a restaurant in downtown Portland — Breakfast at the Hyatt Centric’s restaurant in downtown Portland

What To Eat and Drink in Portland

The thing that always impresses me about Portland is the incredible diversity of the food scene. Some cities impress with their high-end dining choices, some shine by showcasing the regional cuisine, and others have ethnic enclaves that conjure up an alluring version of the faraway by highlighting back-home, back-then dishes in the here and now. Portland has ALL of this—and spans the entire budget spectrum so every palate can be pleased at every price point.

But Portland is too diverse, dynamic, and sizeable to do its full food footprint justice in just one Portland weekend getaway. Believe me, I’ve tried! These are just some of the most worthwhile places for fine food and fun drink that Portland is famous for.

Click to Check Out the Best Portland Food Tours

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Click to Check Out the Best Portland Food Tours *

Voodoo Doughnut is a legendary Portland institution serving an amazing, imaginative array of delicious, decadent doughnuts. Their famous Maple Bacon Bar lives up to the hype. Show up starving since selecting just one option is next to impossible—and a wasted opportunity.

Voodoo Doughnuts display — Voodoo Doughnut in Portland will make your weekend getaway a little sweeter.

Fried Egg I’m In Love makes incredible egg sandwiches with punny names at bargain prices. Their food cart at Pioneer Courthouse Square was just a 5-minute walk from our hotel. It’s a perfect example of Portland street food culture.

Where other cities do food trucks, Portland does food carts. While trucks often roll away, carts stay. In Portland, they also congregate in pods, often with shared seating, so you can go to one pod and have a variety of choices in a single location. Carts are such a big part of Portland food culture that Travel Portland has launched an app to help navigate all the city’s choices.

Eem has been a sensation since it opened in 2019. It serves amazing Thai food with Tiki bar drinks in a charming airy space. A collaboration between successful serial-Thai-restaurant-entrepreneur Earl Ninson (Lang Baan, Paadee, Hat Yai), Matt Vicedomini of Matt’s BBQ, and Eric Nelson of the roaming pop-up drinkery Shipwreck, this place tickled my taste buds, warmed my heart, and filled my belly. Try their signature White Curry with Brisket Burnt Ends—Yum!

Burn Brisket Ends, lunch at Eem in Portland — Smoked Pork Krapao at Eem

Nong’s Khao Man Gai is a one-dish wonder! And that’s a good thing! In Thailand, it’s not unusual for restaurants to focus on just one dish. To open just such a restaurant was Nong Poonsukwattana’s plan when she came to Portland from Thailand. Now people come from all over all day to enjoy Nong’s chicken and rice. Unless you love liver, ask for extra chicken if you order the Khao Man Gai Piset (large portion); there’s really nothing special about the liver.

Ox I’ve been a big fan of playing-with-fire cooking since going to Francis Mallmann’s Patagonia Sur Restaurant in Buenos Aires in 2008. So, I was excited to finally eat at this Argentine-inspired, James-Beard-Award-winning restaurant that makes magic with a giant wood-fired grill. The grill dominates the dining room view and dazzles diners’ palates. Dining with two friends, we managed to knock off 12 dishes, multiple bottles of wine, and some after-dinner cocktails. Every single thing was delicious! None of us can wait to go back!

Lamb chops at Ox — Lamb Chops at Ox Restaurant, one of the highlights of this Oregon weekend getaway

Tusk Awash in white, with a lovely outdoor deck, this Food & Wine Magazine Restaurant of the Year has been winning hearts and accolades since it opened in 2016. The kitchen masterfully melds the Mediterranean with the Middle Eastern. The beautiful dishes are not just a feast for the eyes, but add up to a genuine feast.

Serratto is a slow-food-focused Italian- and French-inflected restaurant whose focus on fresh local ingredients and skillful preparation in the kitchen translates to satisfaction at the table. We ate with the same friends from Ox, same MO: Order generously, course everything out, share each dish, then dish out the feedback. Every single selection was a winner—one fine meal!

Seared Sea Scallops at Serratto Restaurant during our weekend getaway to Portland

Olympic Provisions started out as Portland’s first salumeria and now serves brunch, lunch, and dinner in its restaurant in a restored industrial building in the Southeast Neighborhood. Plenty of charcuterie, sure, but also eclectic snack, salad, sandwich, small and large plate offerings, including some unexpected seafood choices like manila clams, branzino, and octopus. We went for the salumi but couldn’t stop there, and found all of our surf and turf choices quite satisfying.

St. Jack is a restaurant that pays homage to the cuisine of Lyon, France, and what we saw when we snatched glances at nearby tables looked incredibly appetizing. But even we can eat only so much, so we just stopped in for creative cocktails. Great vibe, great drinks, great service!

Scotch Lodge and the bar at Takibi were two bars that came highly recommended by Portland people in the know while we were there, but we couldn’t get to them. You can only drink so much, right? Scotch Lodge is known for its inventive cocktails, extensive whisky selection, and food menu that goes well beyond tasty bar bites. Esquire Magazine just named Takibi as Portland’s best bar, but it’s also a fire-centric Japanese restaurant in a beautiful space that offers an expansive outdoor deck as well. I look forward to checking out both of these spots when next in Portland.

Craft Breweries and Pubs Needless to say, Portland is also one of America’s beer capitals. The city is packed with great craft breweries, tap rooms, and pubs offering a truly stupendous variety of locally made draughts. You won’t have any problem finding plenty to fall in love with while you visit. For IPA fans, Stormbreaker has a great selection of award winners. Breakside brews a slew of creative choices, many of them fruity.

If you’ve read my Mendocino restaurant article, you’ll know I prefer Belgian beers, and one of the best places for those is the Prost! Pub.

Enjoying a beer by the fire at the Prost Marketplace food cart pod

Things To Do in Portland When You’re Not Eating

Portland is a city with a population of over 650K. Its attractions are diverse and numerous enough to pack itineraries for at least a dozen Portland weekend getaways. Mike and I dedicated our most recent trip to updating our knowledge of the food scene while catching up with friends after a long absence from a city we’re quite fond of.

Whether you’re celebrating a couples getaway in Oregon, touring with your friends, or getting back out on the road with the family, you know best what you like to do between meals when visiting a city worth visiting.

What follow are just some suggestions of things we’ve really enjoyed doing in Portland. Let your personal interests guide you to find those things that you think will most satisfy you in this quirky, inventive, interesting, endearing city.

Pioneer Square in Portland — Pioneer Courthouse in downtown Portland, Oregon

Portland people love the outdoors, and one great place to do three great things outdoors is Washington Park. The first is to visit (for free) the International Rose Test Garden, which comprises acres and acres of almost endless varieties of roses in a near-story-book setting.

The second is to check out the Portland Japanese Garden, which actually offers 8 different styles of Japanese gardens. Each reflects various elements of Shinto, Taoist, or Buddhist philosophy. The on-site Kashintei Tea House is a beautiful structure in which to take part in a traditional tea ceremony.

The third thing is to explore the vast expanse of Washington Park that you still haven’t seen while enjoying the first two options. Trust me, Portland knows how to do greenery.

Another open-air activity that is a Portland staple is the Portland Saturday Market. It offers over 250 booths of locally made art, clothing, toys, and other crafts. If you work up a hunger shopping, know that there are plenty of food booths to offer a quick fix for your predicament. Keep in mind that, despite its name, the market is open both Saturdays and Sundays, from 10 am to 5 pm.

Portland is a city of diverse neighborhoods, so it’s fun to get a feel for at least a couple by just walking them. We hit Mississippi this trip, and it was definitely happening. Technically North Mississippi Avenue, this long stretch of vibrant shops, music venues, breweries, brick-and-mortar restaurants, and a sizeable cart pod offered a nice walk, punctuated by shop stops, beer breaks, and some actual in-person chat sessions with a number of friendly locals.

Strolling down Mississippi Street is a fun way to spend a few hours in Portland — Strolling down Mississippi Avenue is a fun way to spend a few hours in Portland.

In addition to the aforementioned Pearl District, some other areas you might want to stroll and investigate are the Alberta Arts District, Nob Hill with its impressive Victorian and Craftsman mansions, and Hawthorne, a vegan hub dotted by vintage shops and clothing boutiques.

For a more structured option, the Portland Art Museum is a fine choice. It’s the oldest art museum in the Pacific Northwest, with a large collection of European, Asian, and American works. However, it is perhaps most proud of its Native American Gallery, which houses more than 5,000 ancient and modern objects produced by more than 200 tribes.

Lastly, no trip to Portland would be complete without a visit to world-famous Powell’s Books. It’s the largest independent bookstore in the world and is open 365 days a year, selling new, used, and rare books. It’s so big you get a map of the store upon entry. Be sure to check out its calendar for when you plan to be in town. They have so many author events, you might be shocked by who you’ll have a chance to see in person when you visit.

Hood River

Just an hour east of Portland, Hood River is a city at the scenic crossroads of the Columbia River Gorge and the Cascade Mountain Range. The city derives its name from the actual Hood River, which flows through town before emptying into the Columbia River.

At this point along its course, the Columbia flows along the bottom of the gorge that shares its name. This stretch of water flanked by high walls of cliffs is home to strong, almost constant winds, making it a magnet for windsurfers, kiteboarders, and sailing enthusiasts.

Just south of the city of Hood River is Hood River Valley, a fertile agricultural region best known for its abundant fruit orchards. Besides providing picture-postcard landscapes as fruit trees blossom in spring and turn color in fall, the valley supplies a steady stream of fresh produce to area markets and restaurants.

This combination of natural beauty, abundance of outdoor-activity options, and flavorful ingredients is complemented by a restaurant scene eager to transform the local agricultural bounty into memorable meals. As a result, Hood River is the perfect place for incredible weekend trips in which you work up a mighty appetite playing in the outdoors all day, then satisfy your hunger in style at a welcoming eatery once you’ve put all your toys away.

Historic buildings in downtown Hood River, Oregon

Where To Stay in Hood River—Best Western Plus Hood River Inn

Situated on the bank of the Columbia River and an easy walk from the Hood River Waterfront Park, the Hood River Inn is a perfectly located home base for those who want to get out onto the river to engage in their favorite water sport or just sit back and soak up the gorgeous river views.

A full range of rooms is available, many with a private balcony that looks right out onto the river. And if water sports on the Columbia aren’t enough for you, the hotel’s fitness center, large outdoor pool, hot tub, and sauna provide plenty of exercise and relaxation opportunities right on the property.

Less than a mile from the heart of downtown, the Hood River Inn is also conveniently close to all the eating, drinking, and shopping offerings of Hood River. But it’s also nice to know that the hotel has a restaurant of its own that is well worth sticking around for.

The pool at the Best Western Plus Hood River Inn

Where To Eat and Drink in Hood River

Riverside I was very pleasantly surprised by how thoroughly Mike and I enjoyed the Hood River Inn’s own restaurant, Riverside. But we’re not alone. In a recent article in Sunset Magazine, the author ranks her meal there as one of the top 5 of her life. Like her, we enjoyed not only the scrumptious food, but the spectacular setting as well. Luckily, no one needs to choose between the breathtaking views of the Columbia and the mouthwatering menu offerings; just savor it all.

The sun reflects off the Hood River alongside the patio at Riverside Restaurant.

3 Rivers Grill Perched high on a hill at the corner of Oak and 6th Streets, 3 Rivers Grill serves up high-end meals in a relaxed atmosphere. Top-quality American classics come out of the kitchen, while the deck offers vistas of the Columbia River down below. Combining great food with fine service in a charming location is the time-tested recipe that has long made this restaurant one of the most popular spots in town.

Mike’s Ice Cream Housed in a picture-book pastel cottage on a charming stretch of Oak Street, Mike’s Ice Cream is a Hood River institution. It opened in 1986 as a place where youngsters could not only get delicious ice cream but chill in a safe, wholesome hang out. All these years later, Mike’s remains one of the town’s favorite places in warm weather. The ice cream is still delicious, still draws a crowd, and still can be paid for only in cash.

Patrons line up for tasty, cold treats at Mike’s Ice Cream in downtown Hood River.

Broder Øst This eastern outpost of Portland’s Broder restaurant group serves up Scandinavian breakfast and lunch favorites in its cozy spot inside the Hood River Hotel downtown. The Danish pancake balls known as Aebleskivers are a fluffy delight, and the Swedish Hash is a hardy breakfast wake-up call. Swedish Meatballs and Gravlax Smørrebrød (a house-cured salmon and shrimp-salad tartine) are two sure-fire winners at lunchtime. The full bar offers a long list of Aquavits and Nordic cocktails.

Evoke Winery & Tasting Room Dating back to 2005, Evoke has been producing wines from the best Pacific Northwest grapes. Their hand-crafted approach to award-winning winemaking can be tasted in every glass. And what better place to enjoy such tastes than in their downtown tasting room, which offers a winning blend of stylish elegance and let-your-hair-down comfort. Whether inside or on the charming deck, Evoke is a great place to toast the delicious offerings of Hood River.

The Evoke Tasting Room in Hood River — Evoke Tasting Room in Hood River

Things To Do in Hood River When You’re Not Eating

Hood River’s location makes it the ideal place to explore and engage with the dramatically beautiful natural area of which it is a part. For those who already enjoy wind-powered water sports, Hood River is no secret. For those who are eager to try out these sports, Hood River offers the perfect opportunity to get started.

Waterfront Park offers multiple launch points and The Hook—a specially designed protected area for beginners to take lessons and build their skills. In addition, the Port of Hood River provides an extensive list of certified instructors eager to expertly teach you what you need to know to safely get going in your sport of choice.

The Hood River Marina, with the Hood River–White Salmon Interstate Bridge and Washington in the background

Cyclists also have many choices in the area. Post Canyon, minutes from Hood River, is a mountain biking favorite. With lots of different terrains and difficulty levels, it has something to satisfy every type and level of mountain biker.

Road riders love the Hood River County Fruit Loop—a 30-mile spin through the rolling hills of the Hood River Valley. The scenic splendor of orchards, farms, meadows, forests, and myriad views of Mount Hood are really all you need. But the 36 members of the Fruit Loop also offer stops at wineries, fruit stands, a country store, a lavender farm, and many other interesting attractions where one can pause, indulge, and refresh along the way.

Hood River’s location within the Columbia River Gorge National Scenic Area means some of the easiest and best things to explore in the area are its waterfalls. Multnomah Falls, Oregon’s tallest waterfall, is also one of its biggest tourist attractions. At its base is Mulnomah Falls Lodge, a gorgeous national historic landmark. Bridal Veil, Shepherd’s Dell, Horseshoe, Wahkeena, and Latourel Falls are a few other water wonders to check out in the area. In total, there are more than 90 waterfalls in Columbia River Gorge!

Upper and lower Multnomah Falls and Benson Bridge in the Columbia River Gorge National Scenic Area

Ashland

Ashland is one of the best weekend trips from Portland, or pretty much anywhere in the Pacific Northwest. And since it’s just 15 miles from the California border, Ashland is also one of the best weekend getaways Oregon has for folks like me from the Golden State. The landscape is gorgeous no matter which direction you’re driving from. Or catch a flight to Medford International Airport (MFR), about 30 minutes north of town.

Since Ashland is best known for its annual Oregon Shakespeare Festival, it comes as no surprise that the town finds itself among The Top 100 Best Small Art Towns in America.

And as one of the notable places on the Rogue Valley Food Trail, it’s also one of the best foodie destinations in Oregon. Of course, everything else is gravy:) (Sorry. Sometimes I just can’t help myself!)

Charming Ashland, one of the best getaways in Oregon

Where To Stay in Ashland—Ashland Springs Hotel

Located in the heart of Ashland, the Ashland Springs Hotel stands tall as a historic downtown landmark. With roots dating back to 1925, the hotel has changed hands and undergone renovations numerous times.

Yet, the hotel has managed to retain its old-world charm and even some of the original fixtures. In the ballroom, six original chandeliers hang from the ceiling, and the original lobby bathroom sinks have been restored and are still in use.

While complete with modern amenities like Wi-Fi, AC, mini-fridges, and flat screen TVs, guest rooms have a cozy elegance reminiscent of European boutique hotels.

The historic Ashland Springs Hotel in downtown Ashland, Oregon

Where To Eat and Drink in Ashland (and Nearby)

For a small town, Ashland restaurants and eateries offer an eclectic mix of dining experiences, from casual vegan options to haute-cuisine wine-pairing dinners.

Additionally, since Ashland lies within the Rogue Valley, some not-to-miss foodie experiences are just a short drive away.

Larks Home Kitchen Cuisine Uber enthusiastic about farm-to-table cuisine, Chef Franco Console creates upscale comfort food with seafood off the Oregon coast, foraged mushrooms, and cheese from local creameries.

Greenleaf A 20-plus-year Ashland institution for good reason. For the outdoor lover, Greenleaf has two great spaces: one on their deck and one on their creekside patio. It will be hard to pick between the two. And with a large international menu that includes favorites from Japanese, Italian, and Indian cuisines, making your entrée choice will not be much easier.

Louie’s is another Ashland restaurant on the main plaza in downtown on the creek. Louie’s probably has the largest menu of all Ashland eateries, with extensive vegan, vegetarian, and gluten-free options among the myriad picks available.

The extensive offerings at Louie’s require separate vegan, vegetarian, and gluten-free menus.

MÄS For the ultimate foodie meal in Ashland, dine at MÄS, just off the main drag. Chef Josh Dorcaka prepares a multi-course tasting menu of innovative Cascadian cuisine (AKA Pacific Northwest cuisine) using seasonal local ingredients. Budget 2 hours for the full gastronomic extravaganza, plus $70/person for lunch or $185/person for dinner.

The Rogue Creamery Make no mistake, this is no small-town cheese shop! The first time I stepped into this creamery and sampled the Rogue River Blue, I knew the cheese was remarkable. A few years later, in 2019, I was rewarded with validation when this blue was awarded the “World’s Best Cheese” title in Bergamo, Italy. If you’re a cheese lover like me, you know you need to make the short trip from Ashland to Central Point (just north of Medford) to check out this creamery.

The best place for wine tasting in Southern Oregon, The Urban Cork

The Urban Cork Want to taste all the best Rogue Valley wines under one roof? Head to the Urban Cork in Medford, Oregon, on Friday or Saturday between 3:00 and 7:00 pm. Order a charcuterie board and sip a flight, a glass, or share a bottle while listening to a local band. With 130 wines from the Rogue Valley and other Oregon appellations, you’ll wish they were open longer!

I must make the full disclosure that the Urban Cork’s owner, winemaker Linda Donovan, has been my best friend since high school. But I assure you, this is an amazing wine tasting room and the only one of its kind in Southern Oregon!

Wine mural at the City Center Wine District in Medford, Oregon, home to the Urban Cork

Things To Do in Ashland When You’re Not Eating

As I said, the Oregon Shakespeare Festival is the number one draw for tourists in Ashland. The season begins in April, with performances through October, and will recommence in 2023. Multiple venues and plays run concurrently, with tickets from $35 to $100. Purchase your tickets ahead of time.

Stroll through quaint downtown Ashland and peak in the boutique shops on Main Street. Circle the main plaza and make your way to the back side, where the creek babbles slowly by. The flowers, the old buildings, the deer you pass on the way there—all add a certain romanticism and make Ashland one of the best couples getaways Oregon has to offer!

Legend has it that the waters of the Lithia Fountain in the main square in downtown Ashland have special healing powers.

Adjacent to the downtown area, you’ll find the 93-acre Lithia Park. With miles of trails, pickle ball and volleyball courts, picnic areas, and a swimming reservoir, you could spend the whole day here (no dogs allowed).

If that’s not enough outdoorsyness for you, visit Crater Lake, the deepest lake in the U.S. Or go river rafting down the Rogue River or Klamath River. We rafted with our winemaker friend, and it was one of our best day trips from Ashland! Or hike up one of the many area mountains for a spectacular view.

View of the Rogue Valley after a mountain hike — View of the Rogue Valley from a mountain hike

Brookings

Admittedly, I have only been to Brookings once, and it was last month. So, why do I consider it one of the best Oregon weekend getaways? Two reasons: the natural scenic beauty and the Dungeness crab (not necessarily in that order).

In the coastal corner of Southern Oregon, we saw an eagle, an otter, seals, egrets, and herons—all from the comfort of our hotel room (more on that later.)

The town itself is very laid back amid its rural surroundings. It’s the kind of place where you see more cows than cars on any commute. I loved it so much I immediately started looking at housing prices to see if I could afford to live there—true story. (For the time being, I’m not moving.)

The view from our room during our weekend getaway in Brookings, Oregon

Where To Stay in Brookings, Oregon—Lowden’s Beachfront B&B

Our room at Lowden’s Beachfront B&B was really more like a one-bedroom apartment, just without an oven or stove. We had a spacious bedroom, a huge bathroom with 2 sinks, a living room, a dining table, a large fridge, coffee pot, and many extras in addition to coffee, like hot chocolate, tea, and oatmeal. Since the onset of COVID, they discontinued the breakfast portion of the B&B, but you can make your own.

The corner room upstairs provided the beauty I fell in love with. Our view out one sliding glass door was the Pacific Ocean. Out the other, we saw the Winchuck River. It rained our first day there, but we didn’t mind. It was so peaceful, we just gawked at all the wildlife and our incredible views.

Our host made us feel very welcomed and comfortable. This truly is one of the best places to stay in Oregon, especially for the price. The only downside—no online reservations. To book a room, call 800-453-4768.

Lowden’s Beachfront B&B, one of the best places to stay in Oregon

Where To Eat and Drink in Brookings

This is where the second part of why I love Brookings comes in: the Dungeness crab. There are 6 major crab ports in Oregon, and Brookings is one of them. Brookings is also one of the biggest Chinook Salmon harbors on the Pacific Coast. So, if you’re a foodie here for the weekend, make sure you try both of these Oregon seafood specialties. And really, like some of the other coastal cities we’ve visited recently in California such as San Francisco, Santa Barbara, and enchanting Mendocino, the seafood in general is fresh and plentiful.

Catalyst Seafood Restaurant My number one pick for best restaurant in Brookings doesn’t take reservations, so you may have to wait for a table when you walk in, or enjoy your meal at the bar. They serve Dungeness crab in so many ways—crab cakes, on pizza, on steak—but I ordered the Whole Dungeness Crab two nights in a row. It was that good! So were the Steamer Clams with andouille sausage. And as a nice bonus, the meals were surprisingly affordable! About half the price I pay for Dungeness crab in SoCal—when I can find it.

Dungeness crab, a must-eat on this foodie weekend getaway in Oregon

Black Trumpet Bistro If you are looking for options other than crab, try Black Trumpet Bistro. If you read my post on what a bistro is, you may be expecting certain traditional French foods at this Brookings restaurant. However, you are just as likely to find classics of Italian cuisine, and some good old American dishes.

Pacific Sushi and Grill Everyone we talked to in Brookings recommended Pacific Sushi for the freshest sushi in town. But sushi’s not the only menu item worth coming for. Other popular items include tempura, veggie rolls, grilled fish, and even the burger.

Chetco Brewery Tap Room Looking for a place to hang out with the locals? Chetco Brewing Company has a taproom for you. This hand-crafted beer house is committed to making vegan beers “without any additives, extracts, or artificial anythings.” There are 20 beers on tap, including IPAs, Lagers, Browns, Reds, Porters, Stouts, and Hefeweizens. They don’t serve food, but food trucks come by regularly.

Steamed Clams, another foodie favorite in Brookings, Oregon

Things To Do in Brookings When You’re Not Eating

Enjoy the natural wonders of Brookings, Oregon. Rivers, beaches, parks, redwood forest—Brookings has it all.

The stunning coast of Harris Beach State Park, along with its large bird sanctuary (aptly named Bird Island), make it a wonderful place to spend a few hours or a day.

Surf or fish on the sandy beach at Crissey Field State Park or walk the trail to Whale Head Beach, 7 miles north of Brookings. Or for more of a hike, take the Oregon Redwoods Trail.

If you fall in love with this area like I did, you may want to visit Chetco Valley Historical Society Museum to learn more about the history of the Chetco River and its people.

The beautiful Oregon coast at Harris Beach State Park

What’s Your Oregon Weekend Choice?

Without a doubt, Oregon has much to offer. With its gorgeous coast, towering redwoods, scenic mountains, Columbia River Gorge, cultural offerings, and culinary bounty, there is plenty to explore and enjoy. A weekend trip to Oregon gives you a wonderful opportunity to indulge in at least some of its treasures.

Whether on the water, in the foothills, or among the attractions of the state’s biggest city, the best getaways in Oregon can be enjoyed in small bites. Or, you can course them out and make your very own moveable feast. Either way, Oregon awaits. It’s time to dig in.

6 Best Oregon Weekend Getaways for Foodies in 2024