So Much to See on the Road from Portland to Ashland

With seemingly endless mountains, valleys, and crisp air, an excursion from Portland, OR, to Ashland, OR, is one of the best road trips that you can take. Come with us now as we travel between these two wonderful places, and find out what you’ll see along the way! Once you arrive in the theater town of Ashland, be sure to enjoy the best of what the area offers. Download our free Ashland Vacation Guide for recommendations on the town’s top galleries, museums, entertainment, and more!

What to See on a Trip From Portland to Ashland

Evergreen Aviation and Space Museum

Our first stop on our road trip is the Evergreen Aviation and Space Museum. We could spend the entire day here, but let’s settle on a few hours. That’s still enough time to check out some of the Museum’s most fascinating exhibits! Explore the World War II Aircraft area and take a journey through wartime history. Or, alternatively, explore the Titan II missile from inside its missile silo, and simulate what a real missile launch would be like! The museum is constantly offering new things to see throughout the year, so you can always look forward to something new at this one-of-a-kind museum.

Silver Creek Falls

After your stop at the Evergreen Aviation and Space Museum, take your time to enjoy Oregon’s natural and beautiful scenery. Silver Creek Falls is right on the way! Called the “crown jewel” of Oregon State parks, this waterfall stands out for its breathtaking beauty and majesty. And if it’s lunchtime, the day-use area is perfect for an outdoor picnic. (If you are looking for more waterfalls to explore near Ashland, read our blog on Ashland waterfalls!)

Oregon Shakespeare Festival

The final stop on our trip is the Oregon Shakespeare Festival. Established nearly a century ago, it is one of the oldest and longest running theater companies in North America! There are three theaters: the Allen Elizabethan Theatre, the Angus Bowmer Theatre, and the Thomas Theatre. Between the three of them, they offer 11 incredible shows over an eight-month season. A classy theater show is a perfect way to end your incredible road trip and begin your vacation in the heart of Southern Oregon.

Enjoy the Best of What Ashland Offers

Situated at the edge of Ashland, Country Willows B&B Inn affords visitors the best of what the area offers. With onsite hiking trails along with proximity to a vibrant downtown, our guests have a unique opportunity to enjoy Ashland’s natural beauty by day and the vibrant city by night. 

When you book any of our elegant countryside rooms, like The Sunrise Suite, you can always look forward to the best amenities, packages, and top-notch service. A daily farm-to-table breakfast, made with the freshest local herbs and produce, is always included in your stay! If you are ready for your next Southern Oregon getaway, check our availability and book your stay today. We can’t wait to hear about your adventures from Portland to Ashland!

If you are looking for more fun things to do during your road trip from Portland to Ashland, remember to download our free vacation guide!