10 Day Oregon Journey
- drwalker4
- Oct 17
- 8 min read
Many of you have been asking for a road trip itinerary of Oregon — and since I’m always encouraging movement and physical activity, our family decided to take a trip to celebrate just that!
Day 1: San Jose → Shasta City (5 hours 30 minutes)
Play in the river at Castella, CA — Castle Crags State Park Campground.---Hike to Heart Lake 2.2 mile hike round trip – park at Castle lake parking.
Hike to Heart Lake (2.2 miles round trip). Park at the Castle Lake parking lot.
Day 2: Lava Beds National Monument → Crater Lake
Explore the caves at Lava Beds National Monument — we did all the beginner caves and a few of the more challenging ones. (1.5-hour drive)
Drive to Mazama Campground at Crater Lake (1.5 hours).
Day 3: Crater Lake
Crater Lake boat tour – Hike down the 1-mile Cleetwood Cove Trail full of switchbacks to the boat dock. It’s a 700 ft climb back up, so make sure you’re at least moderately fit! Give yourself at least 40 minutes to get down. I recommend booking an early morning boat for easier parking.
Swim in Crater Lake after your tour — bring a swimsuit and save plenty of time to hike back up!
Drive 1 hour to Umpqua’s Last Resort (a lovely glamping and RV spot near waterfalls).
Day 4: Umpque Hot Springs, Toketee Falls & Blend
We started the morning exploring the Umpqua Hot Springs and Toketee Falls, just a quick 20-minute drive apart.
Umpqua Hot Springs – These natural hillside pools overlook the river and are clothing optional, so if you’d prefer fewer “free spirits,” go early in the morning. The highest pool is the hottest, and they gradually cool as you move down toward the river — such a unique experience!
Toketee Falls Hike – This short 0.8-mile round-trip trail leads to one of Oregon’s most iconic waterfalls. The view from the main lookout is stunning, but if you’re adventurous, you can scramble down a very steep side path to the base of the falls (definitely proceed with caution).
After soaking and hiking, we drove about 2 hours to Bend — one of our favorite stops of the trip.
In Bend, we spent the afternoon floating down the Deschutes River, which takes around two hours depending on the current. Be sure to do the rapids section — it’s mild but so much fun! We rented our gear from Tumalo Creek, which includes bus service back to your car — super convenient.👉 Tumalo Creek Rentals
Afterward, we checked into our lovely hotel right on the river, the Riverhouse on the Deschutes — perfect for a hot shower and some relaxing downtime.👉 The Riverhouse
We ended the evening with dinner at Spork, a Vietnamese-inspired restaurant concept that’s both creative and delicious — one of our favorite meals of the trip.👉 Spork Bend
Day 5: Smith Rock Hike
We had a nice breakfast in Bend and drove 35 minutes to Smith Rock State Park. We hiked the Misery Ridge Trail (3.6 miles, 908 ft elevation gain), which passes the famous Monkey Face climbing spot. It’s exposed, so go early if it’s hot.
We stayed halfway to Mt. Hood in Madras, OR at the charming Inn at Cross Keys Station — clean, great breakfast, and a pool for the kids. We did laundry here too! Dinner was a simple hotel meal after a Safeway run — fried chicken, salad, and fruit. Cheaper, lighter, and easier than eating out.
Day 6: Mount Hood
We woke up, ate breakfast at our historic hotel, and hit the road for Mount Hood — a day full of easy hikes, a little wild foraging, and family-friendly thrills.
Trillium Lake loop — About 2 miles around the lake. We wandered the shoreline, picked thimbleberries and huckleberries (best in summer), and just enjoyed the reflections of Mount Hood on the water. Wild foraging was a highlight — so yummy and so simple.
Umbrella Falls — A short, sweet 1-mile round-trip hike that’s perfect if you want something quick and scenic.
Alpine Slide / Rollercoaster — We went for a few runs on the alpine slide (the Skibowl alpine slide is basically a summer rollercoaster) and the kids — and adults — loved it. Pure silly-family fun.
Lunch / Pub: We grabbed a bite at the famous Ratskeller in Government Camp — great local pub food and drinks after a morning of activity.
We actually had a campsite reserved, but it poured all afternoon, so we opted for a hotel that night instead (worth it since we needed to be up early the next day for an adventure that required tickets and a specific start time).
On the drive toward our hotel near the gorge, the sun finally came out — perfect timing to stop at Oxbow Regional Park. We pulled out a camping-style dinner (meat, noodles, fun drinks), let the kids wade and play on the sandy beach, and relaxed before bed.👉 https://www.oregonmetro.gov/parks/oxbow-regional-park
Day 7: Columbia River Gorge
We had breakfast at our hotel near the gorge, just about ten minutes from Multnomah Falls. It was a simple Comfort Inn, but super convenient. We got up early to eat since our check-in time at the falls was 9 a.m., which is a great time to go — your permit through Recreation.gov gets you in, but it doesn’t guarantee parking, so being in the first group really helps. Make sure to get your permit at least a month ahead since they fill up fast.👉 https://www.recreation.gov/timed-entry/10089144
We did the 2-mile round-trip hike to the top of Multnomah Falls and back down — it’s as iconic and beautiful as it looks in pictures, and totally worth the climb.
After that, we headed to Sugar Pine Drive-In for lunch before our next activity — their food is amazing and it’s right on the river, perfect pre-ride fuel.👉 https://sugarpinedrivein.com/
Next up was Biking the Gorge with this company:👉 https://bikethegorge.org/
Our check-in time was originally 3 p.m., but since we didn’t camp at Trillium the night before, we got there early. I called, and they were able to bump us up to a 1:30 start, which worked out perfectly since we planned to head to Portland for dinner. The ride takes you past four waterfalls, and you can stop and walk to each one — it was amazing biking through all that scenery. If you don’t bike regularly, definitely get an e-bike; the route is about 12 miles round trip.
After our ride (they recommend 2–3 hours so you have time to stop, explore, and pick a few blackberries along the way), we drove to Portland and grabbed dinner at one of the city’s famous food truck pods — Hawthorne Asylum was our favorite.👉 https://hawthorne-asylum.res-menu.com/
We stayed that night at a Best Western near the airport, which was great because the kids could swim and it made it easy to pick up my mother-in-law, who joined us for the next leg of the trip.
Day 8: Oregon Coast - Seaside Beach, Cannon Beach and Rockaway Beach
We wanted to have a lovely breakfast before hitting the coast, so we got up early and headed to Proud Mary Café in Portland. It’s well known for its amazing coffee, and I had a delicious chai that totally hit the spot.👉 https://proudmarycoffee.com/pages/portland-cafe
After breakfast, we drove about two hours toward the coast. Along the way, we stopped to pick wild blackberries — we ended up with four bowls full and snacked on them for the next few days. So yummy!
Our first stop was Seaside Beach, Oregon, which is known for its boardwalk. It’s got that classic beach-town energy — kind of reminded me of the Santa Cruz Boardwalk. Fun to see, but not totally our vibe, so after walking around for a bit, we continued south.
Next was Cannon Beach, and it was absolutely beautiful. We stopped for lunch — there are so many great fish and chips places, it’s hard to choose just one — and then explored the town, which really reminded me of Carmel with its cute shops and beachy charm. The highlight, of course, was Haystack Rock, which did not disappoint.
Bring binoculars if you can — I couldn’t see the puffins with my naked eye and was so bummed!👉 https://www.cannonbeach.org/
A little farther down the road, we stopped at Hug Point, which was such a fun surprise — little sea caves and a small waterfall right on the beach.
The waterfall is pretty tiny in the summer, but still worth a stop.👉 https://stateparks.oregon.gov/index.cfm?do=park.profile&parkId=137
We ended the day in Rockaway Beach, staying at the Surfside Resort. It’s an older motel, but it’s right on the beach, and the location couldn’t be better. Walking along the sand at sunset was the perfect way to end the day.👉 https://surfsideocean.com/
For dinner, we went to El Trio Loco, a local Mexican spot where the fried whole fish was incredible.👉 https://www.eltrioloco3.com/
Day 9: Oregon Coast – Tillamook Creamery, Heceta Head Lighthouse, Sea Lion Caves & Coos Bay
We woke up and had a cozy breakfast in our suite at the Surfside Resort, then packed up and headed out for another day exploring the Oregon Coast.
Our first stop was the Tillamook Creamery, where we did the self-guided walking tour, watched the cheese being made, and of course tried the cheese curds and ice cream — both so good!👉 https://www.tillamook.com/visit-us/creamery
Next, we made our way to the Heceta Head Lighthouse. If you can, try to get there earlier in the day — there’s often traffic and the parking lot is small. We spent a while playing on the beach below and then walked up to the lighthouse. The views were beautiful and it felt like such a classic Oregon Coast moment.👉 https://stateparks.oregon.gov/index.cfm?do=park.profile&parkId=86
Just down the road is the Sea Lion Caves, which ended up being one of my favorite stops. You take an elevator 150 feet down to sea level, where you can view the cave through large windows — there are usually anywhere from 25 to 150 sea lions lounging and barking inside. It’s definitely smelly but so incredible to see up close! You can also look out through another opening in the cave and see the Heceta Head Lighthouse from a completely different perspective.👉 https://sealioncaves.com/
That evening, we drove down to Coos Bay, where we stayed the night. It’s a small lumber town and we didn’t spend much time exploring, but we had a delicious dinner at EZ Thai, which had lovely service and really good food.👉 https://ezthaior.smiledining.com/
Day 10: Oregon Coast – Bandon Beach, Tree of Mystery and Eureka
We had breakfast at our hotel in Coos Bay before heading out to Bandon Beach, which ended up being one of my favorite beaches on the Oregon Coast.
The rock formations are incredible — I especially loved the one shaped like a wizard’s hat. At low tide, you can explore the base of the rocks and find tons of sea anemones and starfish; it’s like walking through a vertical tide pool. Definitely try to go at low tide if you can — it makes the experience even better.
After exploring the beach, we drove south into California to visit the Trees of Mystery — a beautiful redwood park where you can walk along elevated canopy trails and ride a gondola through the treetops. It was such a fun and unique experience! Plan for about 2–3 hours here depending on how quickly you explore.👉 https://treesofmystery.net/
Afterward, we continued our drive and spent the night in Eureka, ready for the next day’s adventures.
Day 11: Drive Home
Drive home day — 5 hours and 30 minutes. No sightseeing this day, just a stop in Healdsburg, CA for lunch. This was our only event, but I have to share this restaurant since they had a wonderful tea menu, which was so exciting for me.👉 https://thetasteoftea.com
And that was the last thing on our trip — all the way home.
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