Haystack Rock in Cannon Beach, Oregon.

9 Best Oregon Towns For A Weekend Trip

Oregon is one of the most geographically diverse states in the United States. Many of its cities are filled with mountainous terrains, lush forests, and quaint historical backdrops. Here, you can enjoy activities such as hiking, fishing, and sandboarding without the noise of the city. Hood River, Astoria, Joseph, Sisters, and more, are a few examples of the nine best Oregon towns for a weekend trip. Want to capture the beauty of Oregon’s wonderful atmosphere? Then plan your weekend trip! You can relax in fine resorts like SurfSand and chat with locals while exploring museums like the Three Sisters Historical Society & Museum.

Jacksonville

Jacksonville, Oregon
Jacksonville, Oregon. Editorial credit: Underawesternsky / Shutterstock.com

Established in the mid-1850s during Oregon’s gold rush era, Jacksonville is a quaint area at the foothills of Miller Mountain that draws the attention of tourists far and wide. Formerly known as the primary financial hub of South Oregon, Jacksonville feels like a step back in time as its historic district comprises a collection of 19th-century landmarks that continue to be preserved by recent community efforts. Places like the Jacksonville Cemetery and Beekman House Museum are examples of ancient structures that have stood the test of time. Peter Britt Gardens and the Beekman Native Plant Arboretum are good spots to see during the cool of the day, exploring the community’s flora and fauna while using the scenery as backdrops for photographs. Wine Country Inn is a fine accommodation option that will keep you relaxed and at ease.

Cannon Beach

Cannon Beach, Oregon
Cannon Beach, Oregon. Cannon Beach. Editorial credit: quiggyt4 / Shutterstock.com

Cannon Beach is a dreamy getaway in Oregon, known for its breathtaking scenery and artistic charm. Its iconic Haystack Rock, a towering sea stack standing 235 feet tall, is a must-see and is part of the Oregon Islands National Wildlife Refuge. The golden beaches stretch for miles, offering perfect conditions for long walks, tidepool explorations, and even birdwatching. Just north of town, Ecola State Park provides panoramic ocean views, lush hiking trails, and a glimpse of the Tillamook Rock Lighthouse.

For a dose of culture, visit the Cannon Beach History Center & Museum to learn about its maritime past, or browse the many art galleries featuring works from talented Pacific Northwest artists. Whether you are indulging in fresh seafood, enjoying live theater performances, or simply soaking in the riverine atmosphere, Cannon Beach makes for a fantastic weekend retreat. Book a stay at SurfSand Resort, an oceanfront hotel with stunning views and top-tier amenities that will have you feeling like you are home.

Sisters

Sisters, Oregon
Sisters, Oregon. Editorial credit: Bob Pool / Shutterstock.com

Set at the base of the Three Sisters Mountains, the idyllic Sisters is filled with Old West heritage and outdoor adventure. Its lively downtown, set along Cascade Avenue is brimming with boutique shops, cozy cafes, and galleries like Hood Avenue Art Gallery and Sisters Arts Association which put the spotlight on regional art.

Nature lovers will appreciate the easy access to the Deschutes National Forest, where hiking, biking, and horseback riding trails lead to picturesque spots like Suttle Lake and Peterson Ridge Trail. It is famous for its lively events, including the Sisters Rodeo, the world-renowned Sisters Outdoor Quilt Show, and the Sisters Folk Festival, drawing tourists year-round. History buffs can explore the Three Sisters Historical Society Museum before unwinding at The Cottage Inn at Sisters which is a boutique lodge that perfectly captures its rustic charm.

Hood River

Windsurfers in the Columbia River at Hood River, Oregon.
Windsurfers in the Columbia River at Hood River, Oregon. By EncMstr - Own work, CC BY-SA 3.0, Wikimedia Commons.

Often dubbed the “Windsurfing Capital of the World,” Hood River is an adventure-seeker's paradise right at the heart of the Columbia River Gorge. With its prime location at the confluence of the Columbia and Hood Rivers, it has outstanding conditions for windsurfing, kiteboarding, and paddleboarding. Beyond water sports, Hood River is also the gateway to the Mount Hood Scenic Byway leading to breathtaking alpine landscapes and year-round fun.

For a taste of history, visit the Western Antique Aeroplane and Automobile Museum which is home to an impressive collection of vintage planes and cars that will blow your mind. Art lovers can check out local galleries like the Columbia Center for the Arts and take part in the Hood River Art Walk. For a relaxing stay, book a room at the Columbia Gorge Hotel and Spa, famous for being an elegant retreat with spectacular views and world-class hospitality.

Joseph

Chief Joseph sculpture in Joseph, Oregon.
Chief Joseph sculpture in Joseph, Oregon. Editorial credit: benedek / iStock.com

Surrounded by the stunning Wallowa Mountains and rich in Native American heritage, Joseph was once known as Lake City, it was renamed in honor of Chief Joseph of the Nez Perce tribe. Joseph’s downtown district is known for its striking bronze sculptures, a result of its deep connection to metalwork through the Valley Bronze foundry.

ou may enjoy the Joseph Center for Arts and Culture where exhibits celebrate local artists and the region’s indigenous chronicles. Wallowa Lake State Park is a must-see and it is open for activities like fishing, boating, and hiking, all in a picturesque alpine setting. Travelers can take a ride on the Wallowa Lake Tramway to the top of Mount Howard for panoramic views or explore the rugged beauty of the Iwetemlaykin State Heritage Site. After a day of adventure, unwind at the cozy Bronze Antler Bed and Breakfast which has a good reputation for its complimentary breakfast and is located near art studios and restaurants.

Astoria

Astoria-Megler bridge over the Columbia River near Astoria, Oregon.
Astoria-Megler bridge over the Columbia River near Astoria, Oregon.

The oldest town in Oregon, Astoria is a treasured destination for travelers as it is known for its coastal beauty. Perched along the Columbia River, where it meets the Pacific Ocean, it boasts an iconic landmark called the Astoria Column, a 125-feet-tall tower with breathtaking panoramic views of the river and the coastline. It was originally modeled to be an electric tower to rival the Eiffel Tower in France but now forms a significant part of Astor Park with green spaces for outdoor activities. For those who want to know about Astoria’s development, check out the Columbia River Maritime Museum which provides fascinating insights into its seafaring past while the Heritage Museum explores Astoria’s Native American and pioneer history.

Film lovers will enjoy a visit to the Oregon Film Museum, housed in the old Clatsop County Jail which doubles as a filming location for "The Goonies." Take a scenic stroll along the Astoria Riverwalk, hop on the Astoria Riverfront Trolley, or see the bustling downtown famous for being home to the charming Blue Scorcher Bakery and Cafe. End the day with a stay at the Cannery Pier Hotel and Spa where riverfront views meet luxury comfort or cross the enormous Astoria-Megler bridge over the Columbia River on your way to Washington state.

Mosier

A vineyard in Mosier, Oregon.
A vineyard in Mosier, Oregon.

Though small in size with a population of about 500 people, Mosier is packed with natural beauty, vineyards, and plentiful activities that make it a fantastic weekend getaway. Located along the Columbia River, this peaceful place is overlooked by breathtaking views and thrilling outdoor activities beginning with a scenic hike or bike ride along the Mosier Twin Tunnels Trail, a paved path that winds through cliffs and shows off spectacular sights of the river below.

Nature lovers will be drawn to Mosier Creek Falls where a short, one-mile round-trip trail leads to a stunning waterfall and a serene swimming hole perfect for hot summer days. You may see Totem Plaza, home to a striking 29-feet-high totem pole that symbolizes key moments in the town’s past. After a day of exploring, enjoy authentic Mexican cuisine at La Vaquita Taqueria before settling in for the night at Mosier House Bed and Breakfast which was formerly known as the Jefferson Mosier House but has now been converted to an inn that captures its warm and welcoming spirit.

Florence

People walk along the boardwalk in Florence, Oregon.
People along the boardwalk in Florence, Oregon. Editorial credit: Manuela Durson / Shutterstock.com

On the mouth of the Siuslaw River, you will encounter Florence, which is just perfect for a weekend getaway. It is dubbed as Oregon’s playground despite being a historic district on the coasts of the Pacific. For those fascinated by history, landmarks such as the Heceta Head Lighthouse which is 56-feet tall, and the Siuslaw Pioneer Museum are ideal destinations to begin your trip. Here you can find exhibits about its pioneers while getting scenic views of the coast. Interestingly, the lighthouse has now been transformed into a bed and breakfast where you can get good accommodation.

For adventurers, the Sea Lions Caves are just perfect to start the trip. The Sea Lion Caves in Florence are the largest in the United States with a height close to that of a twelve-story building. The best time to visit this cave is during the winter months when the sea lions are gathered for breeding. Other places to see include the Oregon Coast Military Museum which has life-sized exhibits devoted to real-life events, and also the River Gallery which has magnificent pieces that you would just want to buy for your homes.

Yachats

Yachats, Oregon
Yachats, Oregon

Known as the "Gem of the Coast" thanks to its unique location at the base of Oregon’s coast and its many stunning ocean vistas, Yachats is a scenic coastal village with a name that is derived from the Indigenous Siletz language which means “dark water at the foot of the mountain.” The community’s coastline is dotted with many landmarks such as Thor’s Well which is a circular rock formation that has been rumored to drain the ocean away.

You can also go to the bay area which has parking spaces and a seafood restaurant. If the coastline has brought out the explorer in you, be sure to see the 804 Trail which runs through the entire stretch of the beach and links with Amanda’s trail. From here, you can easily access Cape Perpetua which is a hotspot for tourists during the summer. Other monuments you will not want to miss include the Smelt Sands State Recreation Site, Yachats Ocean Road State Natural Site, and Yachats State Recreation Area which are good to spend the afternoons. After a day of touring, rest comfortably at Yatel Motel which is well known for its hospitality and amazing rooms.

What more can you ask for when looking for a weekend trip, these relaxing towns in Oregon have it all. From state parks in Astoria to beaches in Yachats and districts in Mosier, you are not short of things to do in these cities. All you have to do is clear your schedule, create a list of places you must see, and take a camera along, or better still, use your phone to document the memories. When you look back at them, you would be glad you took the time off.

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