Take a day to explore Portland. Stop at the famous Voodoo Doughnuts! Consider planning a day trip to Willamette Valley for an afternoon of wine tasting.
Drive the historic Columbia River Highway and set aside time to explore the Columbia River Gorge. Remember this area is popular during the summer months, so you'll want to arrive early.
Heading south to Bend perhaps detour to see Oregon's most famous volcano Mt. Hood to enjoy some beautiful views. While in Bend, the High Desert Museum is worth a visit.
Smith Rock State Park is about 40 minutes from Bend. This is one of the prettiest state parks you've probably never heard of. Don't miss the hiking trails along the Crooked River.
The Painted Hills are best viewed/photographed in the late afternoon right before sunset. There's also a scenic drive to take through the park and a few short trails.
Crater Lake
You'll want to get to Crater Lake National Park early. Enjoy viewpoints, a hike to the lakeshore, or boat tours. Plus try the beautiful Castle Crest Wildflower Trail.
Drive Oregon's stunning coastline! Stop at Cannon Beach, with its famous Haystack Rock and nearby Ecola State Park. You can enjoy fresh seafood in Newport and visit Cape Mears.
Consider an overnight stay in Pacific City, known for its laid-back vibe. Visit Oceanside Beach State Park to Tunnel Beach where you can explore a rock tunnel.