Quick Getaways from Portland, Oregon: Long Weekend Road Trips

Outside Portland, Oregon, you'll find a whimsical Pacific Northwest setting with numerous activities and spots to explore. Whether you're a Portland local itching to get out of town or flying in for a retreat, we've compiled some of the best destinations near Portland, OR for the perfect weekend getaway.

1. BEND, OREGON

Located about 3 hours southeast of Portland, you will find the town of Bend. This vibrant mountain town on the edge of the Cascade Mountain Range has both natural beauty and urban amenities, making it an ideal destination for those who want a variety of activities.

THINGS TO DO IN BEND

Bend is your ideal escape for adventure and quirky attractions, making it a perfect weekend getaway.

Start your day with an invigorating hike along the Deschutes River Trail, where you can enjoy stunning river views surrounded by ponderosa pines. Refuel at the cozy Wildroots Coffee House, where you can savor locally roasted coffee and homemade pastries in a warm, inviting atmosphere. For water activities, you can head to the serene Hosmer Lake for a unique kayaking experience, gliding across crystal-clear waters that mirror the surrounding mountains.

As you work up an appetite, prepare to taste some of the best food you can find in Oregon. Indulge in globally inspired street food at Spork, a local favorite known for its farm-to-table delights, or cool off with artisanal flavors at Bontà Natural Artisan Gelato.

To taste Bend’s culture, stroll along the Roundabout Art Route, where you'll discover over 20 captivating public art installations throughout the city. As evening approaches, cap off your Bend experience by visiting the iconic Tower Theatre downtown. Catch a live performance, from music concerts to comedy shows, in this historic art deco venue, providing the perfect balance of entertainment and local exploration to end your weekend escape.

WHERE TO STAY IN BEND

For your place to call home during your trip, stay with the highly respected Bend Vacation Rentals by Arrived. The 100 Collection™ proudly partners with this outstanding company, offering meticulously cared-for properties tailored to every need. Arrived Owner Jennifer Mucha sets a gold standard of going the extra mile for those who stay in her rentals. They have cozy townhomes perfect for couples or small families, providing an intimate retreat with all the comforts of home. For groups of 4-6, check out their mid-size escapes, which often feature outdoor spaces like decks or patios to enjoy Bend's beautiful weather.

2. CANNON BEACH, OREGON

About one and a half hours northwest of Portland, Cannon Beach is an iconic coastal town known for its expansive shores, substantial rock formations, and charming downtown.

THINGS TO DO IN CANNON BEACH

Beach exploration is a must in Cannon Beach. Visit the famous Haystack Rock, or go beachcombing during low tide for something more interactive. Take a horseback ride along the beach for a different coastline experience. If you're traveling with kids, Cannon Beach has the perfect sand for building sandcastles or flying kites on breezy days.

Cannon Beach has a thriving art scene worth exploring, with numerous galleries and annual art shows. Nature lovers should visit Ecola State Park for stunning ocean views and wildlife spotting opportunities. The town is also a sweet spot for food lovers, offering artisanal coffee shops, fresh seafood restaurants, and local wine tasting.

Cannon Beach is also a haven for food lovers. Start your day with artisanal coffee and pastries at Sleepy Monk Coffee Roasters, a local favorite. Enjoy fresh seafood at local restaurants like The Wayfarer, where ocean views complement the delicious cuisine. End your day by sampling local wines at the Wine Shack, featuring bottles from Oregon's wine country.

WHERE TO STAY IN CANNON BEACH

For your Cannon Beach vacation rentals, we recommend Beachcomber Vacation Homes. They offer a variety of comfortable and well-appointed properties for any group size or preference. Their beachfront cottages allow you to fall asleep to the sound of waves, providing an authentic PNW experience. Pet owners will appreciate Beachcomber's pet-friendly options, allowing you to bring your furry friend along for the adventure! Regardless of which property you choose, Beachcomber ensures all their rentals are impeccably maintained and stocked with essentials for a comfortable stay, allowing you to focus on making memories in Cannon Beach.

3. ARCH CAPE, OREGON

Located about 1 hour and 40 minutes from Portland, Arch Cape is a hidden gem south of Cannon Beach that offers a more secluded coastal experience. This small community between the Pacific Ocean and the coastal forest is a perfect retreat away from busier tourist areas.

THINGS TO DO IN ARCH CAPE

Must-visit attractions include Hug Point State Recreation Site, where you can explore sea caves and a seasonal waterfall, and Oswald West State Park, offering hiking through old-growth coastal forest.

Take a short drive to the Pilot House Distilling to taste local craft spirits. Here, you can sample artisanal spirits featuring unique botanicals and local ingredients. Learn about the distilling process and the art of crafting small-batch spirits from knowledgeable staff.

Arcadia Beach State Recreation Site, just south of Arch Cape, offers a less crowded beach experience with ample room for long walks. This stretch of coastline is perfect for picnicking and beachcombing, with interesting rock formations to explore.

WHERE TO STAY IN ARCH CAPE

Beachcomber Vacation Homes extends their excellent selection of vacation rentals to Arch Cape, providing comfortable and scenic accommodations for your coastal getaway. For those who want to be as close to the water as possible, their beachfront bungalows offer direct access to the sand. For a more secluded experience, consider their forest cabins tucked away in the coastal woodland.

4. SUNRIVER, OREGON

Located about 3 hours and 20 minutes from Portland, Sunriver is a quaint town along the Deschutes River, offering year-round adventures.

THINGS TO DO IN & Around SUNRIVER

Mount Bachelor is just a short drive from Sunriver, with plenty of things to do year-round. With over 4,300 acres of lift-accessible terrain, it's a popular resort during the ski season. Come summer, the same slopes offer excellent hiking and mountain biking opportunities, including scenic chairlift rides for gorgeous views of the Cascade Range. Families with children will enjoy summer tubing or the thrilling zip-line courses.

The Sunriver Nature Center & Observatory is a must-visit attraction, combining education with entertainment. Here, you can learn about local flora and fauna, enjoy stargazing sessions, and attend raptor programs. Don't miss the chance to explore natural and cultural history with the whole family at High Desert Museum.

WHERE TO STAY IN SUNRIVER

For your Sunriver vacation rentals, we highly recommend Cascara Vacation Rentals. Families or groups looking to be close to Sunriver's amenities will appreciate the family-friendly homes, which offer easy access to the resort's extensive network of paved bike paths and community facilities. This family-owned business understands the importance of doing the extra work to make your rental feel like home. Whether visiting with your significant other, family, or a large group of friends, you'll feel cared for in any Cascara space.

These quick getaways from Portland offer a different experience to suit every taste. Whether you're seeking outdoor activities, cultural experiences, or simply a change of scenery, these destinations near Portland have something for everyone!