10 Perfect Destinations for a LOVE Weekend in Oregon 1063 Likes18 Inquiries

Oregon is a land of endless variety. From rugged coastlines and snow-capped mountains to lush forests and high desert vistas, it offers something for every type of adventurer. Whether you’re craving a peaceful retreat or a lively outdoor experience, these 12 destinations will make your long weekend unforgettable. From hiking in the shadow of towering waterfalls to sipping fine wine in scenic vineyards, let’s explore some of the best places to experience in Oregon this weekend.

1. Ashland: A Cultural Haven

Ashland is a charming gem in Southern Oregon’s Rogue Valley. Famous for the Oregon Shakespeare Festival, Ashland offers a perfect blend of culture, natural beauty, and relaxation. With over 800 performances annually, the festival runs from March to October, making it an ideal time to enjoy top-tier theater. After catching a show, visit Dana Campbell Vineyards for some of the region’s best wines. And if you’re craving some outdoor adventure, head to Mt. Ashland for skiing, snowboarding, or scenic hikes in the warmer months. Relax afterward at Lithia Springs Resort, where the mineral-rich waters will help you unwind.

2. Sisters: Western Charm Meets the Outdoors

Nestled in Central Oregon’s Cascade Range, Sisters is a haven for outdoor enthusiasts. Known for its picturesque western flair, this small town boasts miles of trails, including the popular Metolius River Trail. After a day of hiking or biking, refuel with a warm cup of coffee and breakfast at Sisters Coffee, then head to the local museum to learn about the town’s rich history. Five Pines Lodge offers cozy cabins surrounded by beautiful scenery, with on-site dining at Three Creeks Brewpub for the perfect ending to your day.

3. Cannon Beach: A Coastal Paradise

Famous for its iconic Haystack Rock, Cannon Beach is a must-visit for anyone who loves coastal beauty. Spend your days walking the beach or exploring Ecola State Park, where quiet trails lead to stunning views. The town’s quaint shops and galleries provide the perfect opportunity to pick up a unique souvenir. For a luxurious stay, the Surfsand Resort offers beachside access and a great selection of local restaurants like Wayfarer Restaurant & Lounge.

4. Newport: Oregon’s Historic Seaside Town

Newport is a blend of history and natural beauty. A visit to the Yaquina Bay Bridge offers stunning views of the marina, where you’ll find commercial fishing boats and playful sea lions. History buffs will enjoy exploring the Yaquina Head Lighthouse, while animal lovers should visit the Oregon Coast Aquarium, one of the top-rated in the U.S. For a cozy retreat, stay at the Inn at Nye Beach, offering spectacular ocean views and a relaxing infinity pool.

5. Astoria: Step Back in Time

Astoria offers a rich blend of history and scenic beauty. Located at the mouth of the Columbia River, this town is home to Fort Clatsop, where Lewis and Clark spent their 1805-1806 winter. Visit the Columbia Bar, notorious for shipwrecks, and take a scenic drive to Fort Stevens State Park to explore beaches, shipwrecks, and WW2 history. Stay at the Cannery Pier Hotel & Spa, offering unparalleled views of the river and a peaceful retreat after a busy day of exploration.

6. Hood River: A Thrill-Seeker’s Dream

Located in the Columbia River Gorge, Hood River is a mecca for windsurfers and kiteboarders. You can take a lesson or simply watch the action unfold as adrenaline seekers glide across the river. For a more relaxing day, stroll through Hood River Waterfront Park or explore the Fruit Loop, a scenic route through vineyards and orchards. End your day at the Hood River Hotel with a delicious Scandinavian-style brunch at Broder Øst.

7. Pendleton: A Glimpse of the Old West

Famous for its rodeo, Pendleton is an iconic Western town that offers more than just the Pendleton Round-Up. Visit the Pendleton Woolen Mills to see how the famous wool blankets are made, or check out the Heritage Station Museum to learn about the town’s history. For a unique stay, check in to The Pendleton House Historic Inn, where you can experience the charm of this historic town firsthand.

8. Joseph: Oregon’s Hidden Alpine Gem

In the northeastern corner of Oregon lies Joseph, a town surrounded by breathtaking mountain views. Ride the Wallowa Lake Tramway to the summit of Mt. Howard, and soak in panoramic views of the Wallowa Mountains. This area is rich in Native American heritage, so don’t miss the Wallowa Band Nez Perce Interpretive Center to learn more about the region’s history. Stay at the Mt. Joseph Lodge, offering comfortable accommodations in a truly scenic setting.

9. Newberg: Wine Country at its Best

Just outside Portland, Newberg is situated in the heart of Oregon’s wine country. With over 60 wineries and 120 vineyards, this town offers some of the best wine tasting experiences in the state. Start your wine journey with a guided tour at Domaine Supreme, and explore the charming downtown area. For the ultimate relaxation, enjoy a stay at The Allison Inn & Spa, where you can indulge in luxurious treatments while surrounded by vineyards.

10. Coos Bay: Adventure Awaits

Coos Bay, located on Oregon’s Adventure Coast, offers visitors a perfect mix of excitement and tranquility. Head to the Oregon Dunes National Recreation Area to explore miles of sand dunes or rent an ATV for some thrilling adventure. Afterward, book a fishing charter and try your luck at catching halibut or tuna. For a unique stay, book a Scandinavian-inspired cabin at Bay Point Landing, where you can unwind after an action-packed day.

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11. Silverton: A Garden Escape

Known as Oregon’s “Garden City,” Silverton is a nature lover’s dream. The Oregon Garden, a botanical paradise, offers a stunning 80-acre space filled with native plants. Just outside town, you’ll find Silver Falls State Park and the famous Trail of Ten Falls, where you can hike through lush forests and see breathtaking waterfalls. Stay at the Oregon Garden Resort, nestled right next to the garden, for the perfect nature retreat.

12. Westfir: A Peaceful Escape

Tucked away in the Willamette National Forest, Westfir offers a tranquil escape for nature lovers. This small town is home to Oregon’s longest covered bridge and offers scenic trails through the forest, including the Moon Falls Trail. For a peaceful retreat, stay at the Westfir Lodge, where you can access the surrounding trails and enjoy the serene natural surroundings.

Wrapping Up Your Oregon Weekend

Oregon’s diverse landscapes are perfect for any type of traveler, whether you’re seeking adventure, culture, or relaxation. From coastal towns and mountain getaways to wine regions and historic landmarks, the possibilities are endless. No matter where you choose to spend your long weekend, Oregon will captivate you with its beauty, charm, and endless activities. So, pack your bags and prepare for an unforgettable adventure in one of the most diverse and scenic states in the U.S.