Oregon’s diverse landscapes offer a road tripper’s paradise, blending mountain peaks, high desert, alpine lakes and rugged coastlines. For those craving adventures, even my retired parents who think 3 miles is a LOT, check out this itinerary from Portland to Mount Hood and Bend, before Crater Lake and then back along the Oregon coast. We had the best time exploring the natural beauty of the Pacific Northwest.
I gotta give a shout out to Voyages with Val who gave us the beginning basis of our itinerary.
Day 1 Portland to Mount Hood to Bend
Portland to Bend Distance: 228 miles
Portland to Bend Driving Time: 4 hours 26 minutes
The trip actually starts the night before, arriving in Portland before your big road trip. We flew in and stayed downtown before picking up our rental car the next morning. We always find the best deals with RentalCars.com. As such, we got a later start than originally anticipated (leaving closer to 10 am) from Portland.
We headed out of Portland on the Historic Columbia River Scenic Highway. Our first stop was Vista House, one of the best places to view the Columbia River Gorge. The building is over 100 years old and is open by volunteers from 9 am to 5 pm. There is a small café, restrooms and a gift shop, but be sure to check out the old photographs of the area too.
Next up, you will have your choice of waterfalls, but we stopped next at Bridal Veil Falls. There are two small hikes to do here. From the parking lot, you can head to the left for a short loop that provides an overview of the highway, railroad track and mountains. Or you can continue straight (passing the bathrooms on your left) to a spectacular view of the two-tiered, 100-foot waterfall. Bear in mind, this out and back to the falls is not completely flat and has several sets of stairs. My father decided to stop on the first descent, but if you take your time and move slowly, it’s considered a fairly easy hike.
After this stop we continued on the Scenic Highway to Multnomah Falls. However, the only place to park along the Scenic Highway is at a private parking lot ($20/day). If you want to park for free, be sure to exit the Scenic Highway after Bridal Veil and continue on Hwy 84 to Multnomah Falls, with a short walk from the parking lot to entrance. This waterfall is the most popular and tallest waterfall in Oregon. It has a short 0.25-mile hike to the overlook bridge and a more difficult hike up to the top. You likely won’t need much time here, but they have some food on site and a souvenir shop.
After working up an appetite from the waterfall hikes, head to Hood River. We stopped at Gorge White House for some local ciders and lunch. The food truck operates seasonally so check their website before stopping. We loved the blueberry cider and cherry and sausage flatbread. Picnic tables line the farm with acres of wildflowers and fruit trees for picking.
Your next stops will give you amazing views of Mount Hood. If we had known our weather would be so amazing, we would have tried to spend more time in these spots. After leaving Gorge White House, head to Trillium Lake for some iconic views. You can walk the 2-mile loop around the lake or rent a kayak or paddleboard. Locals come to BBQ and relax on the weekends. Entry is $10/car. These views will be some of the best of Mount Hood but get up close and personal at Timberline Lodge.
Timberline Lodge was built during the Great Depression and was featured in “The Shining.” It offers year-around skiing and scenic hikes. It’s worth going into the lodge to see the historic pieces and watch the film on the making of the hotel.
You will still have a 2-hour drive from Timberline Lodge to Bend. With our later start, we headed to Bend for dinner. If you fly through the itinerary (or start earlier than we did), you may have time to stop at Smith Rock State Park for the sunset. Take Crooked River Trail a short distance to see the iconic views.
Bend has a large brewery scene; as such, we enjoyed dinner at Deschutes Brewery. The elk burger and artichoke dip were excellent. We spent the night in Bend at Waypoint Hotel. Their premium room offered 2 California king beds. They have a great outside patio with chairs fireside and a full bar. In their parking lot is Black Bear Diner, a great spot to refuel before setting out on day 2.
Day 2 Bend to Crater Lake
Bend to Crater Lake Distance: 189 miles
Bend to Crater Lake Driving Time: 4 hours 19 minutes
After breakfast at Black Bear Diner in Bend, we started the 90-mile trek to Crater Lake National Park. Be sure to fill up your rental car as fuel stations are limited around the park. We entered from the north entrance, but when we visited Crater Lake, the 33-mile Rim Drive was partially closed from Phantom Ship Overlook to Skell Head. We stopped at the Rim Village for snacks and bathrooms before driving to Pinnacle Overlook. As I was with my retired parents, we decided to stick to shorter hikes and trails. During our time at Crater Lake, we enjoyed the short walk to see the Pinnacles (definitely worth seeing and the only viewpoint NOT looking at the lake), the Sun Notch loop and the promenade trail from Rim Village to Discovery Point. Check out my post on the full itinerary of things to do in Crater Lake.
Rim Village offers a small café, but we were less than impressed with all the frozen food offered. The Lodge has meals but are quite expensive. I’d suggest bringing snacks or a picnic for the day.
After having our fill of Crater Lake National Park, we stopped at Diamond Lake Resort for dinner. Sitting outside, drinking a local beer with views of the lake and ducks was a great way to end the day. I found a great cabin along Hwy 138 at Umpqua’s Last Resort. It was quite the bougie cabin with air conditioning, electric car charging, a king bed with queen bed in the loft. They offer RVs, glamping and other cabins. They have a wonderfully relaxing atmosphere, and the location helps shave some driving time off the next day’s adventure.
Day 3 Crater Lake (Umpqua) to the Oregon Coast
Crater Lake to the Oregon Coast Distance: 213 miles
Crater Lake to the Oregon Coast Driving Time: 4 hours 20 minutes
Make sure you have things for breakfast at the cabin or you can stop at the country store next door for a few snacks. You will backtrack 15 minutes this morning to make a quick stop at Toketee Falls. It’s a beautiful short hike (with some stairs) to the overlook of a 113-foot-tall waterfall. We really enjoyed this morning walk in the cool air and there are several benches along the way for a break. After the stop, you will continue along Hwy 138 to Roseburg and scenic 101. I would suggest stopping for lunch in Roseburg as your food options are somewhat limited for a little while on the journey.
The rest of the afternoon will be spent driving up the 101 along the coast. Our final stop was Newport for the night. Along the way, we stopped at the Oregon Dunes Recreational Park (Day Use) and took in the views. There is a 4-mile loop you can do that goes along the dunes, or you can just enjoy the viewpoints near the parking lot.
After the dunes, explore the awesome scale of the Sea Lion Caves and the next door Heceta Head Lighthouse. The privately owned cave houses hundreds of sea lions for 9 months out of the year. When we arrived in mid-September, most of the sea lions had migrated for the feeding season. Tickets are $18 for adults and $12 for children. They are opened 9 to 5 pm daily.
As you make your way to Newport, be sure to pull off to some of the beach spots for some great views. If you have time, stop in Yachats for a little stroll through town. In Newport, we stayed at The Whaler, a great spot with beach views near Nye Beach. We couldn’t decide from the many restaurants on offer in town, so decided to have a little progressive dinner – starting with chowder at the Chowder Bowl and moving to Shepard’s pie at Nana’s Irish Pub.
Day 4 Newport to Portland
Newport to Portland Distance: 189miles
Newport to Portland Driving Time: 4 hours 5 minutes
Enjoy some breakfast in Newport before you continue the drive along Hwy 101. Just 15 minutes out of town, you will come to Devil’s Punchbowl – a natural arch off the Oregon coast. If you can time it with high tide, the waves are more dramatic. Google Maps may offer you alternative routes, but the scenic highway has some good views. We stopped and spent several hours at the Tillamook Creamery. They offer tours several times a day for $15 per person, but the self-guided walking tour is amazing and also comes with some free cheese tasting. This co-op, farmer-owned operation has grown dramatically in the last 20 years, and I have to say their ice cream is amazing! The creamery has a large grocer and great food, like mac’n’cheese and cheese curds. Enjoy lunch on site and save room for a scoop of ice cream too. Open daily from 10 to 7 pm.
Spend the afternoon relaxing at Cannon Beach, your next stop and home to The Goonies! The long stretch of beach has the famous Haystack Rock, a 235-foot basalt rock rising out of the water. Enjoy at beer at Pelican Brewing and shop along the main street. Make your way back to Portland and perhaps a few more days in your itinerary.
An Oregon road trip from Portland to Mount Hood, Crater Lake and the coastline is nothing short of magical. Each day offers a unique slice of Oregon’s natural beauty. Whether you are hiking around Crater Lake or marveling at the dunes along the coast, the memories will stay with you long after the journey ends. Pack your bags, hit the road and let Oregon’s wilderness capture your heart.
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