Fall in Love in Oregon: 8 of the State's Most Romantic Weekend Destinations

Home to Southern Oregon University and the Tony Award-winning Oregon Shakespeare Festival, Ashland, Oregon sits in the shadows of the Siskiyou and Cascade mountain ranges, just fifteen miles north of the California border.

Listed on the National Register of Historic Places and a landmark building in downtown Ashland since 1925 is the luxurious Ashland Springs Hotel.

A destination retreat in great part due to the full-service Waterstone Spa, reserve a couples’ treatment room and experience the healing benefits of the region’s naturally occurring lithia mineral water. Catering to weddings, anniversaries, and special occasions, hotel lodging packages for couples at Ashland Springs Hotel feature spa and dining credits, wine and chocolate, and even movie tickets at the local theater.

Less than a half mile stroll to the city’s shopping and entertainment corridor, leave time to explore the Japanese garden and duck ponds at Lithia Park, a 93-acre green space running along both sides of Ashland Creek.

A fairy tale destination for honeymoons and anniversaries, Cannon Beach, Oregon is a quintessential seaside village nestled along the Pacific Coast. Cannon Beach is perhaps best known for Haystack Rock, one of Oregon’s most iconic natural landmarks. Named for its appearance, similar to a stack of hay piled in a mowed field, the monolithic sea stack stands 235-feet over beachgoers at low tide.

A popular Cannon Beach lodging destination for couples is the Stephanie Inn, a premiere oceanfront hotel. The balcony of an ocean-view suite is the ideal excuse to order room service; sleep in late and then request a gourmet chef’s breakfast. Take a bubble bath for two in a Jacuzzi suite or book a side-by-side massage at the resort’s Aveda exclusive spa.

Each room at the Stephanie Inn features a gas fireplace and lanterns for late night walks on the beach. In warmer weather, borrow a beach cruiser bicycle and head into town to explore the shops, galleries and local restaurants. You won’t find any chain stores or restaurants in Cannon Beach – the city actively seeks to support local businesses and preserve the local economy and hometown feel.

Each spring and fall, grey whales make their migration along the Oregon Coast heading towards the warm waters of Mexico in the summertime from the northern waters where they live during the rest of the year. The quaint fishing village of Depoe Bay is well-known as a destination for whale watching all year round, thanks an abundant food supply. Boasting the world’s smallest navigable harbor, the 6-acre fishing port is the heart of Depoe Bay.

At the Whale Cove Inn, each room has a private deck overlooking the stunning Whale Cove Habitat Refuge where you can unwind in a luxurious outdoor soaking tub. The decadence continues with rain-head showers, gas fireplaces, King-sized TempurPedic sleep systems and Tesla charging stations. Guests are also offered complimentary breakfast featuring quiche, homemade pastries, sausages and bacon.

To get up close and personal with whales, sea lions and seals, head out on a whale-watching charter or go deep sea fishing and catch your own meal. For a calmer adventure, visit the shops and restaurants along Highway 101; you can’t go wrong with a burger and bowl of clam chowder at the Chowder Bowl.

Considered the finest luxury boutique hotel in Eugene, the Inn at the 5^th is conveniently located in the heart of the classy downtown district. Welcomed with wine upon arrival, couples can expect the same upscale service throughout their stay.

Rooms feature contemporary design with Italian linens, fireplaces, reading nooks and even places for your pet. Book a massage, body treatment or facial at the property’s full-scale Aveda spa. Later, order a meal featuring French cuisine made with local and seasonal ingredients at Marché, one of Eugene’s most decorated dining establishments.

With sweeping views of the mountains in the distance, couples staying in a balcony suite often enjoy a bottle of regional wine, cider or beer to the backdrop of local musicians performing on the outdoor terrace at the 5th Street Public Market. Hop on the fourteen-seat pub cycle to embark on a two-hour pedal-powered tour of the cities many breweries, wineries and craft distilleries. During football season, Inn at the 5th is also a perfect place to unwind on game day.

Located on the banks of the majestic Columbia River, the Columbia Gorge Hotel & Spa in the heart of Hood River is an easy hour drive from Portland. Seven acres of gardens, an on-site spa, Simon’s Cliffhouse and Valentino Bar are just four of the reasons to book a room at this romantic destination. In colder weather, cuddle up to your special someone in front of the crackling fire in the main lounge.

Described as a boutique hotel within a historic manor, the Columbia Gorge Hotel & Spa is a popular wedding and honeymoon destination. Wineries, orchards and Multnomah Falls, Oregon’s tallest waterfall, draw visitors to the Columbia River Gorge all year round. Plan to spend a morning or afternoon exploring downtown Hood River or watch the kite surfers catching air while walking or biking on the paved paths at Hood River Waterfront Park.

Once a 1936 Catholic schoolhouse, the McMenamins Old St. Francis School has been converted into a 60-room hotel with a pub and brewery, movie theater and live music/event venue. An oasis in winter months, an ornate heated saltwater soaking pool is the property’s gem with an open ceiling for stargazing with your significant other.

At McMenamins, no two rooms are the same and include optional amenities ranging from patios to suites to kitchenettes. Displaying historical photos, memorabilia and students’ artwork, the property is a gallery and museum of sorts. In the newer Art and Ed houses, look for secret hallways and rooms – even a secret bar.

Centrally located in downtown Bend, McMenamins Old St. Francis School is an easy walk to the Bend Brewing Company or Mirror Pond at Drake Park, 13-acres known for community events and the city’s annual 4^th of July celebration.

Running Y Ranch Resort is a full-service resort community located within a 9,600-acre operational ranch. Located eight miles outside of Klamath Falls in the heart of south-central Oregon, Running Y is one hour south of Crater Lake National Park and thirty minutes north of California’s Lava Beds National Monument.

Blending luxury with the many conveniences of home, couples staying at Running Y can enjoy a fully-sorted vacation without needing to venture off the property. With seasonal activities like golf, horseback riding, ice skating and bicycle rentals, there’s no shortage of ways to spend the day together.

Unwind at the Sandhill Spa and fitness center before a romantic yet casual meal at the Ruddy Duck Restaurant. If you feel like staying in, pick up a bottle of wine and fresh ingredients from the shops at The Village and cook together in your suite or private vacation home.

Reputed as of one the finest hotels in downtown Portland, The Benson Hotel has welcomed celebrities, dignitaries, CEOs and other visitors for well over a century. The historic building has preserved its stately elegance, inspired by a romantic European style of architecture.

In the hotel lobby, guests can listen to live jazz music and entertainment every Wednesday through Sunday—making this spot the longest continuously running jazz venue in Portland. Located between Downtown Portland and the Pearl District, couples have many options for dinner reservations, including the property’s on-site restaurant, The Palm Court, or the El Gaucho steakhouse just next door.

During the day, stroll through the Portland Rose Gardens to see why Portland has earned the nickname as The City of Roses. After the sun sets, ride the elevator to the top of the US Bancorp Tower building to toast a nightcap and panoramic views of the city at the Portland City Grill. Time your visit between 6 and 9 pm, when the restaurant doubles as a piano bar.

Many couples celebrating a special anniversary enjoy The Benson’s specially priced packages that include sparkling wine and chocolate dipped strawberries.