What happens when two Seattlelites want more than anything to see the world famous Oregon Shakespeare Festival, but it’s over eight hours of a drive away? The easiest solution, we found, was to add stops along the way to break up the length of the trip, and not pass up the numerous beautiful sites the west coast has to offer.

Here is our road trip guide of what we did and where we stopped to make the most of our trip down to Southern Oregon. We also made a easy Google Maps for you to plan out your trip and add some of your favorite activities.

Seattle to Vancouver, WA ( 3 hours )

To begin our trip we drove to Vancouver, which lies just across the Columbia River from Portland, Oregon.

There is many things to do and see here, including the beautiful five mile waterfront renaissance trail where you can find places to dine and shop on this boardwalk while enjoying the views.

The Pearson Field and Air Museum is popular spot for aviation enthusiasts since the 1900s. Today is remains a popular spot to see historic planes and even have the chance to take one for a drive.

Near Pearson Field lies Fort Vancouver which is filled with historic intrigue.  This park is a former trading post and fort, with lantern tours, many historic buildings and 19th-century blacksmith demonstrations. During the Fourth of July celebration, Fort Vancouver is home to the largest fireworks celebration in the Portland-metro area.

If you are looking for lodging in the Vancouver area, the Hilton Vancouver is the premiere place to stay and right in the center of downtown. The lobby is extensive with high ceilings and three elevators, and is connected to Gray’s Restaurant right next door.

Oregon Coast

Vancouver to Astoria, OR ( 1 hr, 40 mins )

Astoria rests on the coast, right at the mouth of the Columbia River. This was where Lewis and Clark, the famous explorers, finally found the outlet to the Pacific Ocean, so it’s also a site of great historical significance.

With that being said, one of our top spots is the Lewis and Clark National Historical Park. The visitor center includes a replica of Fort Clatsop similar to the one built by the explorers, an interpretive center offering an exhibit hall, bookstore, and two films.

On the waterfront of the town is the expansive Columbia, often filled with large tanker ships ready to set out across the Pacific. There’s a beautiful dock to walk on during the summer days, with the Columbia River Maritime Museum next to it, and an original lightship ‘Columbia’ that you can walk on. Together with the port of the American Pride cruise liner steamships, it’s a marvelous sight. There’s even a vintage style Riverfront Trolley you can take if you have a spare hour, to get any view of the water you could want.

Near the water is the former County Jail, today the Oregon Film Museum, inspired out of the large amount of films that have been filmed in the area. Oregon has had such a large role in use as a location for American filmmaking that it’s gained the nickname of ‘Hollywood North,’ and if you don’t believe us, just look up the list of movies that have been shot there. Most notable is the eighties classic ‘The Goonies,’ of which the opening scene used the jail as a set and allows you to see, looking the same as it did in the film!

Outside the town at Hammond Marina is the site of the ending scene of Free Willy, a can’t miss spot for anyone nostalgic for that film. The museum isn’t only educational, you can even shoot mini scenes on small sets and download them later from the website. Lights, Camera, Action!

Oregon Coast

Astoria to Seaside, OR ( 40 minutes )

Seaside is a small town on the Oregon Coast. Without the frequent traffic of tankers going through the river and any large seaport many miles off, the town is isolated in all the right ways. Sweeping views of the coast on the beach and a small town vibe make this the prime image when you think ‘getaway.’

Within just a few minutes from pretty much every hotel or venue you can find yourself with miles of beautiful coastline. The beaches are incredibly beautiful and remind me so much of the beaches at home with white sand and swimmable turquoise water. The beach next to our hotel was filled with families enjoying the sunshine and children playing outdoor sports, laughing and even some kite flying.

This is a good spot to kick up your feet, enjoy the views and relax. We recommend staying at the lovely Hillcrest Inn and House which is located just one block from the beach. It features 26 units ranging from cozy rooms for 2, to spacious two bedroom cottages for the family. Some of the rooms are pet friendly and others offer Jacuzzi tubs and/or fireplaces, perfect for those romantic getaways.

If you enjoy marine life, or just want some place to take the kids, the Seaside Aquarium is one of the oldest aquariums on the West Coast and offers many fun, educational ways for you to interact with marine life.

Another fun thing that we loved is the Inverted Experience. It’s a cute hole in the wall museum where you can enjoy taking selfie after selfie where everything is turned upside down!

Seaside to Newport, OR ( 3 hours )

Newport sits roughly in the middle of Oregon’s Pacific Coast and is an attractive Victorian tourist favorite and offers many sightseeing attractions.

If you are one to search for the ‘Biggest’ anything or just enjoy a beautiful lighthouse, you can find Oregon’s tallest lighthouse here. It sits 93 feet above a basalt headland that was once lava. One of my favorite things, it there is guided tours where you can walk up the many, many, many steps to see the views and this historic piece.

For more aquatic fun, the Hatfield Marine Science Center is a research facility operated by the Oregon State University. It offers many activities for both kids and adults including octopus feeding, exhibits and educational projects.

Of course, since this is a coastal town, we need to feature our favorite beach. Nye Beach looks west and is a photo-perfect spot to watch the sunset. In addition to the blue water, white sand and sunsets, many shops and restaurants line the streets near the shore, which is great for the beachfront dinner view.

Lastly, one of the most popular tourist sites along the Oregon coast is the Devil’s Punch Bowl. It’s a neat sight to see, because when the waves hit the coast it sends water into the ‘punch bowl’ (naturally carved in a rock headland).

This is another good spot to take a break and rest up, you have a big day ahead of you tomorrow! We recommend staying at the Inn at Nye Beach, they offer pet friendly, beachfront rooms right in the heart of Newport.

“You kiss by the book.” Romeo (William Thomas Hodgson) and Juliet (Emily Ota) fall in love at first sight. Photo by Jenny Graham

Newport to Ashland ( 4 hours )

In southern Oregon lies the small town of Ashland, there you will find one of the greatest celebrations of Shakespeare the world knows today. Every year the Oregon Shakespeare Festival in Ashland runs four classic plays written by the Bard himself, augmented with six or so more non-Shakespeare plays or musicals to beef up the bill. There’s nothing like sitting under the stars, in temperatures that are just right, while world class actors recite Shakespeare in front of you on a stage just like the ones in Shakespeare’s time.

There is many plays to see here so I’d be sure to set up at least two to three days to catch a good handful of them. Some plays are only offered on certain days, so plan wisely.

When attending the festival we highly recommend staying in the Ashland Springs Hotel. It is located in the heart of downtown and within a block away from the festival’s theaters. The hotel itself was built in the 1920’s and after an extensive restoration, looks nearly the same as it looked back then. The opening contains an ornate lobby with a full two story tall ceiling, and color and decor choices that evoke Egyptian hotels from a century ago. Stairs to the upper floors are available, but there is also a small elevator that also puts you right in the period.

Look at that, we made it to Ashland! Here is our full article on the Oregon Shakespeare Festival for your enjoyment. We do hope you make your trip out to Ashland in the near future to enjoy these festivities.





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