Can I pack skydiving, hiking, camping and paragliding into 10 days in Oregon?

Ten days is the perfect amount of time to have the greatest vacation, ever.

If you’re starting in Portland, I’d recommend taking a day to check out the city. It sounds like you and I like all of the same things, so I’m going to give you a hot and fast list of what I would do.

Day 1: Portland

  • Voodoo Doughnuts
  • Stumptown Coffee
  • The International Rose Garden at Washington Park
  • Pittock Mansion

Day 2-3: Skydiving, then the Oregon Coast

  • Check out Skydive Oregon in Molalla. I’ve jumped here before and on a clear day, you can see every volcano on the horizon from Mt. Rainier, to Mt. Hood, St. Helens, Thielsen, Shasta, St. Helens and Bachelor.
  • After your nerves settle, I’d head for the Coast. Lincoln City, to be specific.
  • Check out Devil’s Lake State Park, set up camp and then hit the beach. Lincoln City has great beaches and a lot of fun things to do.
  • You can go glass blowing, paragliding, surfing (get a wet suit- it will be cold-but fun!) and my favorite, hiking!
  • Check out Cascade Head. If you don’t and you see a photo of it at any other point in your life, you’ll seriously regret not going.
  • Camp for a night or two or just stay here the whole time because it’s awesome.

Day 4: More Coast

Just under two hours driving, if you head south on the 101 toward Florence, you’ll find plenty, and I mean PLENTY, of things to keep you occupied. From lighthouses to more paragliding outfitters and surf shops, to Cape Perpetua and the Hobbit Trail to Seal Rock and the Newport Historic Bay District, this drive won’t disappoint. I’d recommend finding a crab shack somewhere along the way to feast more than just your eyes. Yum!

One of my favorite places to camp on the Coast is Honeyman State Park just South of Florence, OR.

Day 5: Southern Oregon

Get some coffee. You might need it by now.

From Florence, I’d head South down the Coast toward Reedsport and then start heading SE toward Roseburg. This little town (Roseburg) is adorable. It’s a great place to check out and a good place to stop for lunch before you continue heading East toward Crater Lake National Park. You’ll drive through Umpqua National Park to get there, which is phenomenal in itself, but also has one of the most beautiful hot springs in the entire state (in my opinion), the Umpqua Hot Springs. From here, you can head south toward Crater Lake, passing Mt. Thielsen and Diamond Lake.

You should definitely stop at the hot springs. And then decide to stay at Diamond Lake campground or drive the extra 12 miles to Crater Lake National Park.

…Honestly, I’d probably check out Diamond Lake first. And, if you’re feeling salty, the hike to the top of Thielsen isn’t bad. It’s long but even if you don’t make it to the top, the views are unbeatable and the air is crisp enough to get you recharged from all the driving.

Day 6: Crater Lake National Park

Okay. This place. Woofta. It’s hard for me to explain in words just how amazing this place is. I actually started crying the first time I saw it. I don’t know why. I don’t know how. I just don’t know. It was beautiful. It was insanely blue. It was huge. And now I tell everyone I can to go visit it and explore the trails and fire lookouts and cliff jumping and camping this place has to offer because I think it seriously changed me. I think I’m going back this weekend.

Day 7:  Maybe stay in Crater Lake another night?

Day 8: Drive North toward Bend. 

Alright, next up, Beertopia, USA. aka Bend, Oregon. Just under a 2 hour drive from Crater Lake National Park and along a windy, emerald green tunnel through Umpqua National Forest, you’ll get to Bend and wonder why you’ve never been here before. You can also stop at the hot springs again if you want! Bend has everything from the Deschutes River running through the middle of town, to more micro breweries and beer than you’ll know what to do with. There’s also Mt. Bachelor, the Cascade Lakes and Smith Rock. If you’re into rock climbing or want an awesome day hike, head to Smith Rock State Park and head up the Misery Ridge trail. It’s about 4 miles round trip but gives you unbeatable views of the area with a handful of (yep, you guessed it) more volcanoes on the horizon.

Not into climbing? Check out Tumalo Falls, the lava fields (and caves) and/or check out downtown Bend.

Day 9: Columbia River Gorge OR Mt. Hood 

This one’s up to you. I love them both and they’re both in the way of you getting back to Portland.

  • If you’re looking for waterfalls, paddle boarding, kite surfing or wineries… I’d head towards Hood River and then drive through the Gorge.
  • If you camp here, check out Eagle Creek Campground.
  • If you’re looking for killer mountain views, a walk through the hotel they filmed The Shining at or pristine alpine lakes, I’d head toward Mt. Hood National Forest.
  • If you camp here, check out Frog Lake, Lost Lake or stay in Government camp and rent a cabin.

Day 10: WHOAH!

What a trip, huh? Sounds like you might be ready for a hot shower and your own bed.