Weekend Trips from Bend, OR

Living in Bend means being surrounded by some of Oregon’s most breathtaking landscapes, but even locals enjoy taking a short getaway now and then. From high desert trails to mountain lakes and historic towns, there are plenty of destinations within a few hours’ drive that make for memorable weekend trips. Each spot offers its own flavor, whether you are looking for outdoor adventure, quiet relaxation, or a mix of both.

Just 30 minutes from Bend, Sisters is a town that feels like stepping into another era. Its Western-themed downtown is lined with boutique shops, art galleries, and cozy cafés. The town is also a gateway to the Three Sisters Wilderness, where hiking and horseback riding trails provide a chance to explore the region’s rugged beauty. Each August, the Sisters Folk Festival draws visitors with live performances and community events, while the annual quilt show in July is a long-standing tradition. For a quick weekend escape that combines charm and natural scenery, Sisters is a favorite.

About 40 minutes north of Bend sits Smith Rock State Park, one of the world’s premier climbing destinations. The park’s dramatic cliffs rise above the Crooked River, creating a striking and inviting landscape. Even if climbing is not on your agenda, the park has hiking trails that range from easy riverside walks to challenging routes like Misery Ridge, which rewards hikers with sweeping views. Photographers are especially drawn to Smith Rock during sunrise and sunset, when the rocks glow in shades of gold and red. A weekend here can be as active or as relaxed as you want it to be.

Located just 20 minutes south of Bend, Sunriver is a popular choice for families and couples alike. This planned resort community has bike trails, golf courses, and easy access to the Deschutes River. In winter, many use Sunriver as a base for skiing at Mt. Bachelor, while summer brings opportunities for kayaking, rafting, and horseback riding. The Sunriver Nature Center and Observatory is a highlight, offering stargazing nights and wildlife exhibits. With a range of vacation rentals and resorts, Sunriver makes it easy to plan a laid-back weekend close to Bend.

A little over two hours southwest of Bend lies Crater Lake National Park, one of the most remarkable natural sights in the country. Formed by the collapse of Mount Mazama thousands of years ago, the lake is known for its intense blue color and incredible depth. The Rim Drive, a 33-mile loop around the crater, provides multiple viewpoints that showcase the lake from different angles. In summer, visitors can take boat tours to Wizard Island, while winter brings opportunities for snowshoeing and cross-country skiing. Though a bit of a drive, Crater Lake is a must-see for those planning weekend trips from Bend, OR.

Roughly three hours north, Hood River sits along the Columbia River Gorge and combines outdoor adventure with a thriving food and wine scene. Thanks to steady winds that funnel through the gorge, the area is a hub for windsurfing and kiteboarding. For those who prefer to stay on land, the Hood River Fruit Loop offers a scenic drive through orchards, vineyards, and farm stands. Local wineries and breweries add to the appeal, making Hood River a great destination for those who want to mix recreation with culinary experiences.

Just over two and a half hours from Bend, Eugene is a city that balances college-town energy with outdoor opportunities. The University of Oregon adds cultural attractions such as museums, theaters, and sports events, while the surrounding Willamette Valley provides easy access to hiking and wine country. The Saturday Market, one of the oldest open-air markets in the state, is a favorite stop for food, crafts, and live music. Eugene’s combination of arts and outdoor living makes it an appealing weekend getaway.

For a trip that is more about the journey than the destination, the Cascade Lakes Scenic Byway offers one of Oregon’s most picturesque drives. The route begins in Bend and winds past alpine lakes, volcanic landscapes, and mountain peaks. Stops along the way include Elk Lake, Sparks Lake, and Cultus Lake, each with boating, fishing, or hiking opportunities. Many travelers choose to camp or stay in rustic lodges along the byway, turning the drive into a weekend-long experience surrounded by nature.

About an hour northeast of Bend, Prineville Reservoir is a hidden gem for those who enjoy water activities. The reservoir is popular for boating, water skiing, and fishing, while the surrounding hills offer hiking and wildlife viewing. The park’s remote location also makes it one of the best places in Central Oregon for stargazing, with clear night skies far from city lights. For campers and RV travelers, the state park has well-equipped sites that make for a comfortable weekend retreat.

A longer trip, but still manageable for a weekend, Ashland is about four hours south of Bend. Best known for the Oregon Shakespeare Festival, this town combines theater, dining, and outdoor adventure. Lithia Park, designed by the same landscape architect who created Golden Gate Park in San Francisco, is a peaceful place for walking and picnicking. Surrounding mountains offer hiking trails and scenic drives, while the town itself has a mix of art galleries, boutique shops, and restaurants. Ashland is well worth the drive for those who enjoy culture alongside natural beauty.

One of the best things about living in Bend is how many destinations are within a short drive. Whether you want to spend your time hiking dramatic cliffs, enjoying small-town charm, or exploring Oregon’s wine country, the options are endless. Weekend trips from Bend, OR, allow residents to experience the variety of landscapes and communities that make the state so distinctive. Each destination offers something unique, creating opportunities for both relaxation and adventure.

Exploring weekend destinations is just one of the many benefits of living in Bend, but finding the right home here takes local expertise. Amanda Johnson brings knowledge of the Bend real estate market, along with a deep understanding of the lifestyle that draws people to Central Oregon. Whether you are searching for a home close to downtown, a property with mountain views, or a place near the region’s trails and lakes, Amanda helps guide clients with personalized support. Reach out to Amanda Johnson today to get started on your home-buying journey.

_{*Header image courtesy of Unsplash}