There’s nothing like a summer road trip to bring me joy! I’m back after a ten-day getaway through Northern California to the Oregon-Washington border and back again — a total of approximately 1450 miles — and thought I’d share some highlights.
Days 1 – 2: Mount Shasta:
Driving about 5 hours north from San Francisco, our first destination was Mount Shasta, a cute outdoorsy town at the foot of (you guessed it) Mount Shasta! The mountain is easily visible (i.e., unavoidable) from highway 5, but this was the first time we’d ever stopped to explore.
A small but fun main street (with a party atmosphere for the 4th of July) features shops, craft beer, and restaurants. Our favorite food experience was a nursery (gardens, not babies) next to our hotel with a pizza kitchen/beer garden in the evenings.
We drove up Mount Shasta to a turnaround point at about 6000 feet, with stops at viewpoints and a couple of short hikes. Beautiful views everywhere we looked!


Days 3 – 4: Ashland, Oregon:
One of my very favorite places! This was our third time visiting Ashland — a fantastic destination for so many reasons, especially the Oregon Shakespeare Festival. The town of Ashland offers a funky mix of boutiques, bookshops, everything from takeout windows to fine dining, and a beautiful park right in the midst of it all.
My highlights (of course) were the two plays we saw. First, in a smaller indoor theater, a gorgeous production of A Midsummer Night’s Dream:
Beautiful lighting, sets, and production design, an incredibly talented cast, and terrific costumes brought this play to glorious life. Loved it! (Read more about the production, here)
The following evening, we saw The Taming of the Shrew in the large, open-air Elizabethan Theater. What a blast! Funny and creative, bawdy, and absolutely engaging. I wasn’t sure that I liked the play when I read it — but experiencing a modern director’s take on the story made me see it in a whole new light.



Check out the very fun trailer:
… or read more about the production, here.
Days 5 – 6: Bend, Oregon via Crater Lake National Park:
Departing Ashland, we drove to Crater Lake National Park, about 2 hours away via twisty back roads. After a very pretty drive, we took in the breathtaking views. We’d been there once before, over ten years ago, and had very overcast weather the whole time. This time around, the skies were clear and the lake’s stunning shades of blue were on full display. We enjoyed a short-ish hike along the rim, had a picnic lunch, drove the perimeter a bit more, then headed on for another 2 hours drive to Bend.
Bend is a town (well, probably more of a city) of about 100,000 people, located along the Deschutes River. The river flows through the center of everything and is surrounded by beautifully maintained parks and walking trails. We did a couple of great walks through town and along the river, and enjoyed our stay in a cute cabin-style motel.


With one full day in the area, we drove to Mt. Bachelor — a winter ski resort open for hiking and mountain biking in the summer. We took the chairlift up to the top, then walked a 4.5 mile trail back down. My husband and I agree — this was our favorite hike of the trip!



We wrapped up our stay in Bend with more picnicking, neighborhood walks, and another stroll along a river path.
Days 7 – 8: Hood River, Oregon:
Our northernmost destination in Oregon! A nice drive led us to the Columbia River Gorge, starting at The Dalles eastward along the river, then working our way west to the town of Hood River, with a few stops to take in the views along the way.


Our hotel in Hood River was situated right along the river. Not only did we have a great view from our balcony, but the property’s gardens offered lovely places to sit and take it all in as well. Our full day in the area was spent chasing waterfalls — simply amazing! One very tough hike was especially memorable: we didn’t quite realize until we were fully committed that it was a much steeper, intense climb than we’re used to! All the falls were gorgeous. What a day!



Day 9: Hood River to Vancouver, Washington:
Leaving Hood River, we drove through the area known as the “Fruit Loop” – a section of northern Oregon with tons of farms stands, shops, and wineries. We stopped at an amazing lavender farm, did a bit of sampling (yum, cherries) at an adorable farm store, and made a few other spontaneous stops before getting back on the road. Leaving that area, our next stop was the Timberline Lodge, an historic ski location on Mount Hood. And yes, there were people skiing on a small-ish patch of snow up on the ridge! In July!



From there, we continued onward to Vancouver, Washington, just across the Columbia River from Portland. We stayed in a waterfront hotel and enjoyed the town’s waterfront park (despite very intense heat!). It was a nice, relaxing way to spend a night before two longer driving days
Day 10: Back to Ashland:
Another five-and-a-half hours of driving took us back to Ashland, where we had the chance to enjoy one more show! This time, we saw Emma, written by playwright Kate Hamill — an incredibly fun re-imagining of the Jane Austen novel. Such a great production, and as always, such a delight to be in the open-air Elizabethan Theater.
For more about the show, including director’s notes and production photos, see here.



The show, plus a pre-show dinner and a night at a sweet little inn, made a perfect final vacation night!
Day 11: Homeward bound
We wrapped up the trip with the long, uneventful drive back to San Francisco. It was good to get home, unpack, unwind, and sleep in our own bed!
And now, it’s time to dream up our next adventure!
Some highlights, for anyone interested in checking out these amazing destinations:
STAY:
- Oak Hill Bed & Breakfast (Ashland)
- Winchester Inn (Ashland)
- Strawberry Valley Inn (Mt. Shasta)
- Wall Street Suites (Bend)
- Westcliff Lodge (Hood River)
EAT:
- Larks (Ashland)
- Hearsay (Ashland)
- The Garden Tap (Mt. Shasta)
SEE & DO:
- Hiking/trails/waterfalls:
- Views & scenery:
- Vista House at Crown Point
- Rowena Crest Overlook
- Timberline Lodge
- Hood River Fruit Loop (farms, fruit stands, orchards, wineries)
- Theater:





I’m glad you had a good time. 🙂 Time well spent.
Thank you!
Wow, what a fun trip! The scenery is beautiful, and it’s so strange to see snow on the tops of mountains in the summer. I also love seeing all the different Shakespeare venues and stages. And I’ll remember this post with all the links if I ever head that way😁
It was so much fun! I couldn’t believe there were people skiing way up there — it was so bizarre walking through the parking lot in 80+ degree weather and seeing people carrying skis and snow gear.
What a fantastic trip. The scenery looks absolutely stunning. Glad that you enjoyed the plays too. It sounds like a great vacation.
Thank you! It was so great to get away and go to new (beautiful) places!
Wow, this looks like an absolutely amazing trip!! Now I want to visit Ashland! I’m not really into Shakespeare, but I think it’s way more interesting in play format than reading it, lol. I’m glad you got to see Crater Lake. We tried to on our honeymoon in July and it was not visible due to cloud cover…they were even calling for snow that day!
I think Crater Lake is very hit or miss in terms of weather — it definitely was not cooperative the first time we tried going there years ago! It’s really different seeing Shakespeare on stage, especially when the production is so creative and dynamic. Ashland is such a great town (and the Shakespeare festival always includes a mix of non-Shakespeare plays, so there’s something for everyone!)
Thanks for sharing your gorgeous photos, the lodging, and all the stops! Checks all the boxes of a perfect road trip! Planning trips could be your side hustle!
Oh wow you took some truly incredible pictures of breathtaking nature scenes on your trip, thank you for sharing! I’ve never been to Oregon but it looks absolutely gorgeous. And also that Elizabethan theater looks like so much fun, I’d love to see an Emma play since I love that book! (& movie adaptations too!)