12 Perfect Destinations for a Long Weekend in Oregon

It is said that variety is the spice of life, and Oregon truly embodies this notion with its diverse geography. From the spectacular coastline to the high desert, soaring mountains, and verdant valleys, you have your pick when planning a long weekend getaway. Hike among the towering waterfalls of Silver Falls State Park, sip wine in the renowned vineyards of Newberg, or stroll along the windswept beaches of Cannon Beach with Haystack Rock as your backdrop. With its rich history, vibrant small towns, and endless outdoor beauty, Oregon is the perfect place to visit on a long weekend.

Ashland

Located in the Rogue Valley in Southern Oregon, Ashland stands out for its culture and resplendent beauty. The Oregon Shakespeare Festival has been a fixture in town since 1935 and has grown to include over 800 performances in a season that runs from March through October. After a show, stop by Dana Campbell Vineyards, one of many local wineries. Wine Enthusiast has even ranked the Rogue Valley among the top five wine regions in the world.

If outdoor excitement is part of your plans, Mt. Ashland is just a few miles away. The highest peak in the Siskiyou Mountains at 7,500 feet offers alpine ski and snowboard trails for all levels, accessible Nordic skiing and snowshoeing trails, great hiking when the snow melts, and spectacular views year-round. After all your activity you will want a relaxing place to unwind, and the Lithia Springs Resort is just the place. The mineral rich waters from beneath the resort are provided for guests to soak in and enjoy in their own private tubs.

Sisters

Located on the eastern side of the Cascade Range, heading toward Central Oregon, Sisters is an outdoor paradise with refined western flair. Hiking and biking trails abound, with favorites including the Metolius River Trail and the Whychus Rim and Creek Loop.

Before setting out, fuel up downtown at Sisters Coffee with a breakfast sandwich and coffee, then stock up on outdoor supplies at Hike-N-Peaks. If history piques your interest, stop by the Sisters Museum for insights into the town’s past. For accommodations, Five Pines Lodge and Spa offers cozy cabins with miles of trails leading into the high desert. The lodge also boasts onsite dining at Three Creeks Brewpub, a local gastropub.

Cannon Beach

This coastal enclave is best known for iconic Haystack Rock, a dramatic 235 foot tall basalt sea stack so close to the beach you can access it at low tide. The beach itself is nearly four miles long and eminently walkable, so while you could spend your entire trip happily watching sunsets and the waves roll in, do not forget the town has much more to offer. Pack a lunch, head just a bit north to Ecola State Park and take the wooded hike along the coastline cliffs down to Indian Beach. You are likely to have it all to yourself to relax and enjoy.

The charming downtown contains an array of quaint businesses, such as C&R Mercantile and Dragonfly Gallery. To learn more about the town's history, visit the Cannon Beach History Center and Museum. The Surfsand Resort is an ideal spot to lay your head, only steps to the beach, and centrally located to restaurant options such as Wayfarer Restaurant & Lounge.

Newport

Newport is traditionally known more as a working town than a vacation spot, which adds to its charm and interest. The Yaquina Bay Bridge, opened in 1936, links U.S. Route 101 north to south and offers a dramatic spotlight into Neport’s historic bayfront. The marina here is fully accessible to the public, and is home to the commercial fishing fleet, research vessels, sailboats, and local sea lions sunning themselves on the docks. As you move over to the coast, start at the Yaquina Head Lighthouse on the north end of town. First put into service in 1873 and standing at 93 feet, it is the tallest of its kind in Oregon. Jutting nearly a mile out into the Pacific Ocean, spectacular views are at hand and it is a prime spot to catch sight of migrating Grey Whales.

Drive south over the bridge to the Oregon Coast Aquarium. Ranked as one of the best aquariums in the United States and dedicated to environmental stewardship, this home to over 350 species of sea life offers exhibits for all ages. The highlight is the Passages of the Deep, an underwater tunnel winding through varied ocean habitats replete with sharks, eels, rays, and more. Stay at the Inn at Nye Beach, which is centrally located right on the ocean in the quaint Nye District. It provides complimentary breakfast delivered to your room and has an outdoor infinity pool with panoramic views.

Astoria

Located at the confluence of the Columbia River and the Pacific Ocean, Astoria exudes old-town charm in the relatively young Pacific Northwest. Founded in 1811 by John Jacob Astor as a fur trading hub, it became the first American settlement west of the Rockies. One of its most notable features is the Columbia Bar, a vast system of shifting sandbars and shoals known as the "Graveyard of the Pacific." This treacherous stretch of water has claimed countless ships, making it one of the most dangerous waterways in the United States. Another highlight is Fort Clatsop in Lewis and Clark National Historic Park, where you can explore a reconstruction of the 1805-1806 winter encampment of the famous expedition. The buildings, based on William Clark’s original sketches, offer a glimpse into the explorers' challenging stay.

To round out your long weekend, take a twenty-minute drive to Fort Stevens State Park, where you can stroll along a wide, windswept beach, explore a historic shipwreck, and walk among World War II gun batteries. The park also preserves a Civil War-era earthen fort, adding yet another layer of history to your visit. If you prefer a scenic drive, you may even spot an elk herd that calls the park home. After a day of exploring, unwind at the Cannery Pier Hotel & Spa, perched atop a pier jutting into the Columbia River.

Hood River

Just an hour east of Portland, Oregon, along the striking Columbia River Gorge, lies the water sports mecca of Hood River. On most days, you’ll see windsurfers, kiteboarders, and wing foilers gliding across the Columbia River, taking advantage of the powerful winds that funnel through the gorge. If you want to join in on the action, Big Winds offers lessons and equipment rentals to help you get started. For a more laid-back experience, Hood River has plenty to explore. Take a scenic stroll through Hood River Waterfront Park, which features a two-mile paved path along the riverbank. If you prefer a drive, the Fruit Loop offers a delightful route through 27 farm stands, wineries, and orchards, where you can sample fresh produce, local wines, and homemade treats.

When it’s time to unwind, check in at the Hood River Hotel, a charming downtown property built in 1911 and listed on the National Register of Historic Places. The hotel’s restaurant, Broder Øst, serves a fantastic Scandinavian-style brunch, perfect for a relaxing morning. For a casual lunch or dinner, stop into the tasting room at pFriem Family Brewers and try their German-style Pilsner, which won gold at the prestigious 2024 World Beer Cup.

Pendleton

If you are visiting Pendleton in September, chances are you’ll witness the world-famous Pendleton Round-Up, now in its 115th year. But even if rodeos aren’t your thing, there’s plenty to explore in this historic town. Pendleton is famous for its wool blankets; you may even own one. Take the free Pendleton Woolen Mills tour to see how they’re made for a unique behind-the-scenes experience.

For those interested in the area’s rich history, the Heritage Station Museum, Tamástslikt Cultural Institute, and Pendleton Air Museum offer fascinating exhibits. The nearby Umatilla and Wallowa-Whitman National Forests provide excellent hiking opportunities if you're up for a challenge. Prefer something more laid-back? For a stay that transports you to another era, check in at The Pendleton House Historic Inn, a charming bed-and-breakfast built in 1917.

Joseph

Tucked in the northeastern corner of Oregon at the base of the Wallowa Mountains, Joseph is remote but well worth the journey. Known as the "Alps of Oregon," this breathtaking region is best seen from above. Visitors can ride on the Wallowa Lake Tramway, the steepest gondola in North America, ascending 3,700 vertical feet to the summit of Mt. Howard. Once at the top, grab a bite at Alpine Grill while soaking in the panoramic views.

The town itself is steeped in Native American history, named after Chief Joseph of the Nez Perce Tribe. You can explore this heritage at the Wallowa Band Nez Perce Interpretive Center, Wallowa County Museum, and Maxville Heritage Center. If the weather is nice, take a 6.5-mile drive to Wallowa Lake Marina to rent a boat, paddleboard, or kayak, or try your luck fishing for trout and kokanee. For accommodations, the Mt. Joseph Lodge sits conveniently between Main Street and Wallowa Lake, offering everything from cozy single rooms to a spacious four-bedroom cabin.

Newberg

Newberg is a short distance southwest of Portland and is a gateway to one of Oregon's heralded wine regions. Located in picturesque Yamhill County, with over 60 wineries and 120 vineyards, it has the most wine makers and growers of any county in the state. Start at award-winning Domaine Supreme for a guided tasting and vineyard tour.

Newberg also boasts a charming historic downtown. Explore the Hoover-Minthorn House and Museum, the childhood home of U.S. President Herbert Hoover, or visit the Chehalem Cultural Center, featuring an art gallery and exhibition hall. When it’s time to unwind, The Allison Inn & Spa offers luxurious accommodations, rejuvenating spa treatments, and scenic walking trails. Don’t miss the multi-course tasting menu at Jory Restaurant for a true farm-to-table dining experience.

Coos Bay

Coos Bay is set along Oregon’s Adventure coast, so be ready to partake in some exhilarating fun. It is located just south of the Oregon Dunes National Recreation Area, North America's largest expanse of sand dunes, extending for 40 miles along the coast. It is spectacular and must be seen to be believed. The dunes contain a network of hiking options, such as the John Dellenback Trail, or if you want to get some adrenaline flowing you can rent an ATV and cruise up and down dunes reaching 500 feet in height.

After all of your activity in the sand, take to the water by booking a fishing trip with Sharky’s Charters or one of the many other charters available. They will guide you to some of the best spots in the Oregon Pacific to catch halibut, salmon, tuna, and more. Keeping in the spirit of adventure, book a stay at Bay Point Landing, which has Scandinavian-inspired cabins and Airstream suites. Both accommodations include fire pits on which to cook your freshly caught fish!

Silverton

Nicknamed Oregon’s "Garden City," Silverton is a paradise for nature lovers. The Oregon Garden, an 80-acre botanical wonderland featuring native plants from the Willamette Valley and Pacific Northwest, is a must-visit. You can take a leisurely stroll or hop on the 25-minute guided tram tour.

Nearby, Silver Falls State Park offers the famous Trail of Ten Falls, a scenic 7.2-mile loop through lush forests with breathtaking waterfalls. If you prefer a shorter hike, there are cutoff points and a newly paved one-mile walkway for easier access. Architecture enthusiasts shouldn’t miss the Gordon House, the only Frank Lloyd Wright-designed structure in Oregon. After a day of exploration, dine at Fin+Foul Kitchen or Oso, which serves Spanish and Mediterranean-inspired cuisine. For a cozy retreat, book a stay at the centrally located Oregon Garden Resort.

Westfir

Nestled in the heart of the Willamette National Forest and the Cascade Range, the tiny town of Westfir is an outdoor enthusiast’s dream. Once a company-owned lumber town, many of its old mill structures remain in use today, adding to its rustic charm. One of its most iconic features is the Office Bridge, the longest covered bridge in Oregon, which spans the North Fork of the Middle Fork of the Willamette River.

Hiking and mountain biking trails abound in the surrounding forest. The Moon Falls Trail offers a short, scenic walk past a 100-foot waterfall, while the Tire Mountain Trail takes hikers through meadows bursting with wildflowers in the spring. If you’re drawn to water, nearby Odell Lake and Waldo Lake are perfect for fishing, swimming, and kayaking. Keep in mind that Waldo Lake is motor-free, preserving its status as one of the clearest lakes in Oregon. Stay at the Westfir Lodge for direct access to trail systems right from your doorstep.

Wrapping Up

Oregon is blessed with natural wonders. Mountain towns, coastal villages, high desert escapes, and idyllic valley hamlets are all on the menu. Deciding on a destination for your perfect long weekend may be the most difficult part of your journey. But rest assured, whichever town you choose, your time will be filled with adventure, culture, and relaxation. So pack your bags and start exploring, Oregon is ready to share all it has to offer.