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An hour of Googling and visiting various winery websites later, I figured out that this was the Sokol Blosser winery, one of the oldest and most famous in the Willamette Valley! We went for a wine tasting and some nibbles, and it was even prettier than in that guide book photo. Total drive time: hours, depending on how many wineries you want to visit.

Where to stay in the Willamette Valley: You can still use Portland as your base for Day 3 since the Willamette Valley isn't that far away. The Eagle Creek Fire was large and dangerous, and parts of the Historic Columbia River Highway and many area hiking trails still remain closed as of November You can visit Vista House at Crown Point and a couple viewpoints, but the rest of the highlights along the highway remain closed.

Multnomah Falls Lodge which was thankfully saved from the fire is also open again via the Interstate 84 parking lot, and this is the best way to visit Multnomah Falls. Check for updates at the Forest Service site. I'm still going to write this section though, because hopefully these areas will be cleared and safe again for visitors and hikers soon! Put on your hiking shoes and make sure your camera is charged on Day 4 of your Oregon road trip, because today you're going to explore the Columbia River Gorge.

This is a river-carved canyon that stretches for more than 80 miles, with the Columbia River forming the boundary between Washington state and Oregon. Seeing Multnomah Falls a foot double waterfall is probably the highlight for most people who visit the Columbia River Gorge, though there are plenty of other beautiful spots to stop and see, too. Be aware that the Highway is very popular during the summer months, and parking at viewpoints and trailheads fills up fast — be sure to pack plenty of patience with you!

In The Dalles, consider the Celilo Inn. I personally recommend staying in Hood River simply because it makes for a cooler drive on Day 5. Hood is considered one of the 7 Wonders of Oregon and is home to the only year-round ski resort in North America yup, on the slopes of a volcano! You probably won't have enough time to hit the slopes, but you can still enjoy the beautiful views.

Then it's time to continue south to Bend , the outdoor recreation mecca of Oregon. Elliot's sister lives in Bend, so that was our main motivation for visiting — but I think this cool little city definitely deserves a spot on any Oregon road trip itinerary. If the weather is clear this evening, head up to Pilot Butte — an extinct volcano in the center of town — for sunset. If you want to be right in the middle of the action, check out The Oxford Hotel , which is right downtown.

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So if you hit one, definitely spend today outdoors! If the weather isn't ideal it happens — it was cloudy, rainy, and cool the whole time I was in Bend in June! And if you want to hit the road again today? Bachelor, Broken Top, South Sister, and 14 different alpine lakes. Total drive time: hours if you drive the entire Cascade Lakes Scenic Byway; about an hour if you just go as far as Mt. Otherwise, Bend Mountain Coffee is a great way to start your morning.

On Day 7, let's head out to some parts of Oregon that you might not find on other road trip itineraries. This is one of the prettiest state parks you've probably never heard of. Elliot and I tackled the Misery Ridge trail it's challenging, but not as awful as its name makes it sound , which took us about two hours to complete.

If a vigorous hike doesn't sound like a great way to spend your morning, there are easier trails along the Crooked River to check out, too. Try the buffalo nachos!

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From Terrebonne, you'll keep going east into Eastern Oregon. This part of the state is woefully overlooked by most tourists my Fodor's guide dedicates only 38 pages to the entire eastern half of Oregon! You know those photos of the Rainbow Mountain in Peru that are popping up all over the internet? Yeah, well you can see essentially the same thing in Eastern Oregon — but minus the strenuous hike, high elevation, and huge crowds! There's a scenic drive to take through the park, as well as a handful of short trails to hike around the hills.

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Where to stay: I would recommend spending another night in Bend. Read reviews on TripAdvisor Book a room here. You'll want to make Day 8 an early one so you can head to Oregon's most famous national park: Crater Lake! It's only about 1. Coming from the north entrance station of the park, you'll skirt Crater Lake for a while on your way to the Steel Visitor Center, where you can watch a film about the lake and get park information.

From there, you can either backtrack the way you came to drive the full mile scenic loop drive, or continue on from the visitor center and go counter-clockwise around Crater Lake. The top thing to do at Crater Lake in the summer is to take a two-hour park ranger-led boat tour around the lake. You can get tickets at the historic Crater Lake Lodge which is also worth visiting. But note that getting to the boat dock requires you to hike down and eventually back up the Cleetwood Cove Trail, which is 1.

This is the only trail that leads down to the lakeshore. If the strenuous hike isn't going to work for you, don't worry — there are plenty of lookouts and shorter hikes around the lake that you can still enjoy. So if you definitely want the full Crater Lake experience, you'll want to plan your Oregon summer road trip in July or August. Where to stay at Crater Lake: The historic Crater Lake Lodge would be a great splurge, but rooms book up months sometimes a year in advance.

Today it's time to head to the coast, because no Oregon road trip would be complete without a day or two spent driving up Oregon's stunning coastline. This route will spit you out in Reedsport, near the bottom of the Oregon Dunes National Recreation Area, which stretches all the way up to the town of Florence.

Spend some time exploring the dunes, and then begin your drive north up the coast on the Some stops you might want to make this afternoon include the sea lion caves in Florence, the small town of Yachats, and the Yaquina Head Lighthouse the tallest lighthouse on the Oregon Coast in Newport, which is where I recommend stopping tonight. Where to stay: I recommend staying tonight in Newport, a little more than halfway up the Oregon Coast.

Today will be a more leisurely drive up the rest of the Oregon Coast, with plenty of time to stop at beaches and eat lots of seafood. Of these spots, Cannon Beach and Astoria are really the must-visits. Cannon Beach is the beach you see on all the postcards, and Astoria was founded in the early s and named after John Jacob Astor. Meanwhile, historic hotel lovers might enjoy Hotel Elliott. If you have extra time to spend, I would probably dedicate it to the Oregon coast — you could do an entire Oregon Coast road trip, there's so much to see.

From Astoria, it's only a 2-hour drive back to Portland. If your flight leaves later in the day, spend a few more hours enjoying the coast, or maybe head back to Portland for one more food cart meal. You step onto the road, and, if you don't keep your feet, there's no telling where you might get swept off to. Join the ADB Community! Sign up here to get exclusive travel tips, deals, and other inspiring goodies delivered to your inbox.

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Wonderful read! Oregon has been on my bucket list for some time now. Smith Rock looks amazing! I feel like certain parts of Oregon get lots of love like the coast and the Columbia River Gorge , but the entire state is so diverse and so pretty! Smith Rock and the Painted Hills were virtually empty compared to some other places we visited.

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Amazing place! Wonderful photos!

I would love to visit Portland, especially because one of my teachers were from Portland and she told us a lot of stories about this magnificent place. What a great itinerary. I have been to most places though on various trips. I think one but road trip sounds amazing but a decent amount of driving as well.