I would put forth the idea that for an active, outdoor vacation, Oregon might be the best state in the country. Why? Geographic variety.
Portland
Oregon’s main city – despite what you sometimes hear in the news – is fun and vibrant. Start here. It really doesn’t matter whether you stay in the downtown area west of the Willamette River, to the neighborhoods to the east, or near the airport – it is easy to get around via light rail. For food and drink lovers, the city has ton of great restaurants, wineries, and breweries.
Willamette Valley
Once you have seen Portland, rent a car and start your real vacation. The famous Willamette Valley is long and often is the focus of Oregon visits for wine lovers. We suggest you prioritize just the northern end of the valley, in the area around Newberg and McMinnville. Spend a couple nights here and visit not only the well-known, larger wineries but smaller outfits you spot along the side of the road.
The Oregon Coast
Your next adventure is to drive west on Highwayt 6 to the Pacific Ocean and then travel north and south on Highway 101. Visit the quaint village of Seaside. Tour the cheese factory in Tillamook. Stop at the Sea Lion Caves where you can watch (and listen to) these massive beasts. The coast is long and wonderful, well worth a few days to explore the various parks.
Eugene or Ashland
If you love the coast, continue all the way south towards California before heading inland to the quaint small city of Ashland. Ashland is sort of a hippy town, famous for its Shakespeare festival but also just a fun place to spend a night. In that area it is also worth visiting Oregon Cave National Monument. Alternatively, jump off from the coast much earlier and head east to Eugene, home to the University of Oregon and a super fun small city. Eugene is a great place to wander, eat, and engage in the many cultural activities the town offers.
Crater Lake
Then, travel further east, up and over the Cascades to Crater Lake, an absolutely stunning lake that fills the crater of an extinct volcano. Definitely spend a night in the national park if you can and make sure to hike on the local trails. Nearby is the Upper Rogue River, which is seemingly swallowed by the earth as it travels through hollow lava tubes.
Bend & the High Desert
Head north to Bend, outdoor recreation capital of the state. This is such a cool, fun small town that we created an entire multisport tour based in Bend. Great food, great breweries, and great outdoor activities. With the Deschutes River running through town, the Cascades just above, and Mount Bachelor as the nearby ski area, Bend seemingly has everything for outdoor adventurers. The city is located in the “high desert” and there is a lot more exploring to do in eastern Oregon but, if you are short on time, at least spend a night in the historic Hotel Condon on the way back to Portland.
Photo credit Visit Bend