Oregon Weekend Getaways
Relax on scenic sandy beaches, explore charming coastal towns or rejuvenate surrounded by nature in a national park.
Craving mountains, coastlines, and charming small towns? I get it, I was too. That’s why I started exploring Oregon one weekend at a time, and honestly, each trip felt like a breath of fresh Pacific Northwest air. In this post, I’ll share the unforgettable weekend getaways I’ve discovered across the state. Where rugged coastlines, misty forests, and cozy little towns make it easy to unplug and recharge. These weekend trips are packed with stunning scenery, inviting places to stay, and outdoor adventures that leave you feeling refreshed and inspired.
Best Oregon Weekend Getaways:
Cannon Beach Bliss at the Hallmark Resort & Spa - 1 hour 30 min from Portland, Oregon
We drove about an hour and a half northwest from Portland (80 miles on US-26) to Cannon Beach (population 1,500), a classic Oregon seaside town. I wandered the downtown streets lined with galleries and saltwater taffy shops, then stopped at the Cannon Beach History Center & Museum (free entry, featuring a replica of a 19th-century longhouse and artifacts from shipwrecks). Of course, the real highlight was Haystack Rock, a 235-foot sea stack rising from the beach, formed 15–16 million years ago.
“I didn’t know rest felt this spacious,” I thought that evening as I stepped into the airy lobby of the Hallmark Resort & Spa ($249). Outside, low clouds draped over Haystack Rock, softening the coastline’s edges; inside, wide windows curved toward the ocean like an embrace. Everything at the resort felt considered, light woods, sea-toned fabrics, and quiet music whispering in the hallways.
What I Loved Most: The gentle lull of waves outside my window, the sea-light shifting across the room like a living painting.
My highlights? For dinner, we ventured downstairs to The Bistro at the resort. I ordered the clam chowder served in sourdough bread bowl and a side salad bright with local greens and shaved carrots. The chowder was rich and creamy, flecked with tender clam pieces and sweet corn kernels, with just a hint of black pepper that balanced its warmth. The bread soaked up the soup beautifully, crust crisp at the edges but soft inside, the smell of toasted grain and brine filling the air around me.
Plan your Hallmark Resort & Spa vacation:
- Drive Time from Portland: ~1.5 hours northwest
- Vibe: Coastal elegance, restful, scenic
- Highlights: Hallmark Resort & Spa, Haystack Rock at sunrise, Ecola State Park hikes, tidepooling, Cannon Beach galleries
- Best Time to Visit: Late spring through early fall for clearer views and comfortable seaside weather
- Cost: Rooms ~$200–$300/night; chowder dinner ~$18–$25
- Hours: Hotel check-in after 4 pm; The Bistro open for lunch and dinner (seasonal hours apply)
Port Orford Quiet & WildSpring Calm - 4 hours 50 min from Portland
We drove about 40 minutes south from Bandon (28 miles on US-101) to Port Orford (population 1,100), the oldest town on the Oregon coast (incorporated 1856). I stopped at Battle Rock Wayside Park, where settlers first clashed with Indigenous people in 1851, then toured the Port Orford Lifeboat Station Museum (built 1934, free entry) with views over the ocean cliffs.
“This is where time feels like a breath held,” I thought as I stepped into my cabin at WildSpring Guest Habitat.I admired 100-foot trees, wooden floors and antique furnishings. The ocean was only half a mile away.
What I enjoyed: The hush in the Guest Hall as morning light spread across the ocean view. I listened to birdsong threading through eucalyptus and fir.
My highlights? Breakfast was a self-serve buffet in the hall. I had homemade granola, local fruit, and organic coffee. I layered bowls of creamy yogurt with crunchy granola and wild berries from Oregon farms.
Later, I relaxed in the hot tub. Steam curled into the chilly air.
Plan your stay:
- Drive Time from Bandon: ~30 minutes south
- Vibe: Forested, restorative
- Highlights: WildSpring Guest Habitat, labyrinth and sculpture garden, whale-watching from spa deck, nearby beach hunting for agates, Port Orford art galleries
- Best Time to Visit: Mid-May through early October for mild ocean breezes and clear skies
- Cost: Cabin stays ~$200–$250/night; breakfast included
- Hours: Guest Hall open daily; spa and grounds accessible anytime to guests
Bend Horizons & Tetherow Calm
We drove just 10 minutes west from downtown Bend (4 miles up Century Drive) to Tetherow (population ~1,200 in the surrounding community). This resort area blends history and modern luxury. Bend itself began as a logging town in 1905, and you can still see remnants at the Deschutes Historical Museum downtown ($6 admission).
“I could stay right here all day,” I thought, sitting on the balcony at Tetherow with a blanket around my shoulders and the smell of sagebrush drifting up from the golf course. The sun was just rising over the high desert, casting long gold shadows across the pines. Tetherow didn’t try too hard, it just let the view do the talking. Everything was modern but grounded, with stone and wood that felt like it belonged to the mountain.
What I Loved Most: The silence between the trees. The kind that isn’t empty, but full of birdsong, soft footsteps, and wind brushing across dry grass.
My highlights? Breakfast at The Row, their casual clubhouse restaurant. I had the huckleberry pancakes, thick and warm with crisped edges, dotted with sweet berries that bled purple into the butter. The syrup smelled faintly of pine and vanilla, and every bite was sweet without being heavy, like summer camp mornings grown up.
Plan your vacation at Tetherow :
- Drive Time from Salem: ~3.5 hours southeast
- Vibe: High-desert luxury, scenic, restful
- Highlights: Tetherow Resort, Deschutes River Trail, Old Mill District, Cascade Lakes Scenic Byway
- Best Time to Visit: Summer for hiking, fall for crisp air and golden light
- Cost: Resort rooms ~$250–$400/night; breakfast ~$14–$20
- Hours: The Row open 7am–9pm; trails open daily
Astoria Waters & Cannery Pier Quiet - 1 hour 50 minutes
The 40-minute drive from Cannon Beach dropped us at the mouth of the Columbia. I walked along the Astoria Riverwalk (6 miles, free access), stopping to watch sea lions barking on the docks, then crossed the 4.1-mile Astoria-Megler Bridge (the longest continuous truss bridge in North America). A side trip took us to Fort Stevens State Park (4,300 acres, $5 day pass) to see the rusting wreck of the Peter Iredale (1906).
“I’d never felt so anchored and adrift at once,” I thought as I stood on the private balcony, watching container ships slide under the Astoria-Megler Bridge. Cannery Pier Hotel & Spa stretched 600 feet into the Columbia River, its bold red façade echoing the old canneries that once stood where I now sat. Inside felt like a warm memory, fireplace lounges, heavy blankets, and the perfect hush of river and fog settling around me.
What I Loved Most: The morning ritual of scanning the river for incoming ships, wrapped in a Pendleton throw with binoculars at hand, it felt like watching time unfold slowly, chapter by chapter.
My highlights? For breakfast I moved down to the lounge where the hot offerings smelled of melted butter and savory sausage. I had an omelette filled with Oregon cheddar and wood-roasted vegetables, steaming beside a plate of waffle squares dusted with powdered sugar. The coffee smelled rich and earthy; each bite and sip was comforting, simple, thoughtful, just right before stepping out to explore.
Plan your stay at Cannery Pier Hotel & Spa:
- Drive Time from Portland: ~2 hours northwest
- Vibe: Maritime history, refined relaxation, river-front calm
- Highlights: Cannery Pier Hotel & Spa, Hall of History exhibit, Astoria Riverwalk trail, Astoria Column climb, Columbia River Maritime Museum
- Best Time to Visit: Late spring through early fall for clearer skies and river activity
- Cost: Rooms ~$300–$500/night; breakfast included; spa treatments and chauffeur rides extra
- Hours: Check-in after 4pm; breakfast served most mornings starting around 7 am; spa and hot tub open evenings
Ashland Springs & Lithia Waters
We drove about 25 minutes south from Medford (16 miles on I-5) to Ashland (population 22,000), a mountain town known for its arts and history. Downtown, I walked to the Ashland Plaza with its 19th-century buildings, then popped into the Schneider Museum of Art (free admission on SOU’s campus). A highlight was the Lithia Fountain, bubbling with mineral water since the 1910s. In the evening, we caught a play at the Oregon Shakespeare Festival (tickets from $40).
“I could feel the centuries in the water,” I thought later as I slid into the deep soaking tub filled with mineral-rich spring water. The air smelled faintly of earth and medicine, the kind of scent that carries history. Lithia Springs Resort felt like a retreat held in the hush of gardens and trees, soft koi pond ripples, fire pit sparkles at dusk, and the quiet rhythms of forest and spring weaving through every corner.
What I Loved Most: Morning tea in the Tea Room, sunlight through wisteria vines, fresh-baked scones waiting on porcelain plates, and the gentle murmur of footsteps outside in the gardens.
My highlights? For breakfast I joined the buffet in the main hall. The air smelled of melted butter, fresh fruit, and pastries. I layered creamy yogurt with granola and berries picked from local farms, the fruit bright and slightly tart, the granola toasted and nutty. Later I lounged by the outdoor saline pool, steam rising from the hot tub under tall trees, and felt the mineral water ease into me like warm light.
Plan your stay at Lithia Springs Resort:
- Drive Time from Portland: ~4 hours south via I-5
- Vibe: Forested, restorative, subtly luxurious
- Highlights: Lithia Springs Resort, Waterstone Spa, Ashland’s Lithia Park, Oregon Shakespeare Festival shows, downtown galleries and eateries
- Best Time to Visit: Spring and fall for garden blooms and moderate temperatures; quieter winter stays for true solitude
- Cost: Rooms ~$200–$300/night; breakfast buffet ~$18; spa treatments additional
- Hours: Check-in after 4 pm; breakfast buffet served 7:30–10 am; afternoon tea 3–5 pm; pool/hot tub open 9 am–10 pm
Arch Cape Inn & Retreat
We drove just 10 minutes south from Cannon Beach (5 miles on US-101) to Arch Cape (population 250), a tiny village tucked against the ocean and forest.
“I hadn’t expected a castle on the coast,” I thought, stepping through the front door of Arch Cape Inn & Retreat ($259). The shingled turret rose above manicured gardens, and inside, the Common Room’s fireplace glowed softly. The building felt like a quiet storybook, wood paneled, softly lit, heavy with thoughtful details. Arch Cape itself was hushed: secluded beaches, fog drifting in through trees, the ocean just steps away.
What I Loved Most: The way the garden and terrace wrapped you in forest shadows and ocean breeze, making the whole place feel private and utterly calm.
My highlights? Breakfast was served each morning in the dining room, chef-made dishes that changed daily. I ordered a vegetable frittata with fresh herbs, seasonal mushrooms, and local greens, served alongside sourdough toast and fruit from nearby farms. The eggs were fluffy and warm, the mushrooms earthy and fragrant, the fruit tangy-sweet. The coffee brewed from Sleepy Monk beans smelled rich and woody. Each bite felt gentle, elegant, and like a soft invitation to slow down.
Plan your stay at Arch Cape Inn & Retreat:
- Drive Time from Cannon Beach: ~10 minutes south
- Vibe: Romantic, forest-tinged, secluded-chic
- Highlights: Arch Cape Inn & Retreat, Arch Cape Beach, Hug Point State Recreation Site, Oswald West State Park, Cannon Beach galleries and Haystack Rock
- Best Time to Visit: Late spring through early fall for longer days and coastal clarity
- Cost: Rooms ~$270–$320/night (based on season); breakfast included
- Hours: Check-in after 4 pm; breakfast daily ~8:30–9:45 am; common areas open throughout day
Portland Pause at the Kimpton Vintage
We flew about 4 hours nonstop from Austin to Portland (this is where we usually start our road trip) and touched down in Oregon’s biggest city (population 635,000). Downtown, I toured the Oregon Historical Society Museum ($10 admission) and climbed up to Pittock Mansion (built 1914, $12 entry) for sweeping views of the city framed by Mount Hood. Powell’s City of Books (a full city block of shelves) was a must before dinner.
“This feels like a tucked-away story,” I thought as I walked into the lobby of Kimpton Hotel Vintage Portland. The city outside was gray and flickering with drizzle, but inside was all velvet chairs, mural walls, and soft lighting that made everything look like evening even at noon. It was stylish without being showy, like someone confident in their own weirdness.
What I Loved Most: The view from our window: rooftops, water towers, and that moody Portland light that turns even parking lots into poetry.
My highlights? I wandered down to Mother’s Bistro & Bar nearby for breakfast. The scent of brown butter and cinnamon greeted me at the door. I ordered the wild salmon hash, crispy at the edges, dotted with red onion, paired with poached eggs and a hollandaise that smelled faintly of lemon zest. It was rich but clean, like comfort food made by someone who knows restraint. I ate slowly, watching streetcars roll past the window, the whole city waking up in layers.
Plan your stay at Kimpton Hotel Vintage Portland:
- Drive Time from Newberg: ~45 minutes northeast
- Vibe: Urban, artistic, quietly luxe
- Highlights: Kimpton Hotel Vintage, Powell’s City of Books, Pioneer Courthouse Square, Director Park, Art galleries nearby
- Best Time to Visit: Late spring through early fall for mild weather and walking-friendly days
- Cost: Rooms ~$180–$280/night; breakfast ~$15–$22
- Hours: Hotel check-in after 3pm; Mother’s Bistro open 8am–2pm daily
Leaving Oregon, But Not Really
As we packed the car for the final stretch, I looked back one last time, at the pines swaying in the coastal wind, at the distant curve of a trail we hadn’t walked, at the places that had opened slowly and stayed with me long after. Oregon didn’t dazzle with spectacle. It gave me quiet magic: a steaming waffle by a foggy window, the hush of a river path, the sudden clarity of a mountain after days of mist.
Each town offered something gentle, a way to slow down, to look closer, to listen. And each meal, each morning view, each road between was part of that rhythm. The state never rushed me. It simply waited, steady as its trees, soft as its beaches, ready to be noticed.
I left Oregon with a fuller breath. Not everything needs to be loud to be unforgettable.
More to explore...
Booking Checklist
1. Book Your Flight - I use Expedia because I like their mobile app with my itinerary. They've helped me re-book flights on many occasions. Once you reach their Gold tier, support is especially good.
2. Book Your Hotel - I use Booking.com or Expedia, depending on my destination.
3. Book Your Rental Car - I use Expedia.
4. Book your tours on Viator or Get Your Guide.
