People walking by the river in Hood River, Oregon.

7 Romantic Small Towns In Oregon For A 3-Day Weekend

Oregon is a state with stunning geographical features, a fantastic yet generally underrated coastline, charming cities, access to the state's wine country, and warm, welcoming towns for people looking to recharge for a relaxing, three-day weekend full of promise. These communities welcome visitors with their unique attractions, access to the Oregon coast, exquisite dining and drink options, and lavish accommodations, perfect for spending an extended weekend. The state has some astonishing hidden gems for residents and out-of-towners alike to indulge their imagination and set the scene for a romantic weekend.

Newport

Fishing boat returning to shore in Newport, Oregon.
Fishing boat returning to shore in Newport, Oregon.

At the western end of U.S. Route 20 is the coastal city of Newport, where visitors are treated to majestic natural beauty, historical districts in town, and glorious coastlines. The Yaquina Bay State Recreation Area is the place to explore and enjoy during an extended weekend. The Yaquina Beach has miles of sand to explore and relax on, and waves to surf on. There are forested parks for the novice or experienced hiking enthusiast, and the Yaquina Bay Lighthouse is a treat to visit and is considered one of the oldest structures in the city. The Oregon Coast Aquarium is a wonderful place to spend the day, with a variety of exhibits to explore, showcasing diverse wildlife, including fish, sea mammals, and birds.

Just north of the recreation area is the Allred Hotel, which offers its guests rooms with alluring views of the Pacific Ocean and Nye Beach. This romantic hotel can host private events, and it has a pool, hot tub, deck, sauna, and an espresso bar in the lobby, making for a comfortable weekend. Not too far from the Allred Hotel and Nye Beach is Nana's Irish Pub, which serves patrons homemade fish n' chips in beer batter, which is only the start to their selection of exciting meals and drinks served in a quaint local setting.

Hood River

Lavender Farms in Hood River, Oregon.
Lavender Farms in Hood River, Oregon. Image credit: Victoria Ditkovsky / Shutterstock.com.

Just 60 miles east of Portland on the Columbia River is the city of Hood River. The city has gorgeous views of the river and landscapes, not to mention views of Mount Hood south of the city, wineries and breweries, and a cozy, warm, welcoming downtown. The Hood River Waterfront Park is a magical place to visit to begin the extended weekend. The park is situated right on the Hood River Waterfront Trail, features Luhr Jensen Beach for relaxation during the summer months, and the Port Marina Park is nearby for boat launches, allowing those who want to fish in the river to further explore it.

The Pines 1852 Winery is a must-see for wine enthusiasts, and its main tasting room is in the heart of the quaint downtown next to Georgiana Smith Park and behind the Hood River Public Library. The Pines 1852 hosts live music events, the space can be rented out, and it can host weddings at the estate. One of the best hotels to spend the long weekend in is the Horsefeathers Hotel, where guests are treated to a contemporary and timeless wonder in the heart of downtown. The Horsefeathers also hosts weddings, reunions, and other events, and provides guests with straightforward access to various restaurants and shops in town.

Brookings

The beautiful beach in Brookings, Oregon.
The beautiful beach in Brookings, Oregon.

On the southwestern end of the state is the coastal city of Brookings, renowned for its stunning coastal scenery and access to the Chetco River. Mill Beach is the spot to enjoy during a sunny day on the extra-long weekend. It's the best spot to enjoy the ocean, gather for a picnic, and visit Table Rock, which is right on the beach. Just north of the beach is the Chetco Brewing Company, which serves patrons world-class beer, tasty food, and hosts private events, making for a fun weekend near the beach.

Another stunning natural spot to visit is Chetco Point Park, a rocky peninsula with peaceful trails and spectacular views of the ocean and landscape for visitors and residents to enjoy during the long weekend. The Mermaid's Muse Bed and Breakfast is a charming place to spend an extended weekend, offering guests breathtaking views of the coast, a private hot tub, a hot breakfast each morning, and an ocean-inspired interior that pays tribute to the mythical sea beings.

Astoria

Overlooking Astoria, Oregon.
Overlooking Astoria, Oregon. Image credit Hrach Hovhannisyan via Shutterstock

Right on the Columbia River, on the very northern end of the state, and next to the Washington State Line, is the city of Astoria, which is the oldest city in the state and an astonishing place to inspire just the right tone when romance is on the itinerary. Right on the water is the Columbia River Maritime Museum, where its visitors can learn more about the river, the history of boating on the river, a 3D theater for people to enjoy, and the Warnock Model Boat Pond on display. The Bowline Hotel is a boutique hotel also right on the Columbia River, where guests can enjoy gorgeous views of the river and the adjacent landscape, comfortable rooms with incredible amenities for a relaxing weekend, and the Knot Bar for drinks for the evening.

Another museum in town is the Oregon Film Museum, where visitors can learn about the legacy of film and television production in the state. The museum is housed in what used to be the Clatsop County Jail, and has galleries honoring the jail, the hit movie "The Goonies" (which was filmed in the state), and guests can get their mug shots taken in the museum. On the western end of town, near the Astoria-Megler Bridge, is the Bridgewater Bistro, where patrons can enjoy a lovely dinner with immaculate views of the landscape and river, get served tasty and sustainable meals, and is an awesome spot to enjoy live music and other various events during the weekend.

McMinnville

An iron horse in McMinnville, Oregon.
An iron horse in McMinnville, Oregon. Image credit Cynthia Liang via Shutterstock

In between the cities of Salem and Portland is the city of McMinnville, also known as the heart of the state's wine country. The Roshni Vineyard is on the western end of town, allowing its visitors to walk through the vineyard, have picnics, and purchase and enjoy wine tastings in the owner's home. Another lively place for drinks in town is the Conservatory Bar, where patrons can enjoy tasty meals and well-crafted drinks in a cozy setting.

Just north of the Conservatory Bar is the Atticus Hotel, a luxurious place to spend the long weekend in style. The rooms are spacious and lush for guests to enjoy, with fireplaces and local coffee and tea, and guests can enjoy a lovely meal in the Cypress Restaurant and Bar in the hotel's lobby. The City Park in town is a relaxing place to enjoy a sunny day during the extended weekend, as visitors and residents have access to the Aquatic Center, access to tennis courts/pickleball courts, and cozy views of the North Branch Cozine Creek.

Dundee

Gravel road and vineyard in Dundee.
Gravel road and vineyard in Dundee.

Just north of McMinnville is the city of Dundee, another astonishing destination in the state's wine country. The Fox Farms Vineyards is a family-owned winery, which has a cozy wine-tasting room in downtown, and has a wine club for people looking to join, and the vineyard hosts private and lavish events in the downtown tasting room or in the Estate Vineyard Party Barn. Another winery to explore in town is the Hyland Estates, which has been open since 1971, has over 185 acres of vineyard vines, relaxing tasting rooms, and also hosts immaculate events to enjoy during the extended weekend.

Nearby, stay at La Bastide Bed and Breakfast, a very relaxing Inn established in 2014 that is inspired by European inns, intending to create a luxurious experience in the state's wine country. The rooms are very comfortable, with a fireplace and views of the vineyards in select rooms, and a freshly prepared breakfast is served at 8:00 a.m. local time. On the northern end of town is the Harvey Creek Trail, a 1.5-mile-long trail giving people spectacular views of the vineyards, the forests all around, and people can enjoy the shallow waters of the Harvey Creek.

Pendleton

The serene town of Pendleton, Oregon.
The serene town of Pendleton, Oregon.

In the northeastern corner of the state, on the Umatilla River, is the city of Pendleton, renowned for its Old West history and outdoor activities. The Pendleton Roundup Grandstand is the place to be in town to enjoy a rodeo, concerts, and much more for a wild and memorable weekend. Just nearby is the Pendleton River Parkway, a three-mile-long walk, giving walkers and bikers pleasant views of the Umatilla River, the landscape around the city, and it is a perfect place to go birdwatching and view wildlife in the river.

On the north side of the river is the Pendleton House Historic Inn Bed and Breakfast, a very friendly and elegant place to visit in the eastern end of the state. The rooms are gorgeous and lovely, it has an in-house loner library, and the Inn can also host lavish weddings for a remarkable three-day weekend. A western-style restaurant to enjoy on Main Street is the Hamley Steakhouse and Saloon, which serves mouth-watering prime steaks, along with other tasty meals for a romantic night out on the town. Hamley also has a western store that sells apparel for people to dress as their inner cowboy and cowgirl, and has home decor and gifts to cherish the memories of Pendleton.

Romance and Relaxation in Oregon

Each of these fascinating communities in the "Beaver State" offers natural wonders to explore, wineries to indulge in, calm and quaint hotels and bed and breakfasts to experience, and history to delve into. These towns have their own unique stories to tell, and are a treat to unwind in as an escape. Whether the towns are coastal or inland, Oregon is a magical state to enjoy a unique and memorable three-day weekend, and it may just be the perfect place to make memories that last forever.

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