9 days in Oregon Itinerary

9 days in Oregon Itinerary

Created using Inspirock Oregon journey maker

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Route & dates

9 days in Oregon Itinerary

Start: Madison
Fly:  8​h 30​min
1
Portland
— 1 night
Drive:  2​h
2
Cannon Beach
— 2 nights
Drive:  3​h
3
Hood River
— 1 night
Drive:  2​h 45​min
4
Redmond
— 1 night
Drive:  3​h
5
Crater Lake National Park
— 3 nights
Drive + Fly:  10​h 15​min
End: Madison

1
night
Portland

Portland ©
A big city with a small-town feel, Portland is home to the country's biggest rose test garden, perched on a hill overlooking downtown.
Start off your visit on the 13th (Tue): hike along Forest Park.

To find ratings, traveler tips, maps, and tourist information, refer to the Portland vacation planner .

Madison to Portland is an approximately 8.5-hour flight. You can also do a combination of bus and flight; or drive. Due to the time zone difference, you'll gain 2 hours traveling from Madison to Portland. In August, daytime highs in Portland are 85°F, while nighttime lows are 60°F. Wrap up your sightseeing on the 14th (Wed) early enough to drive to Cannon Beach.

Things to do in Portland

Parks Nature Trails

Side Trip

Multnomah Falls
Highlights from your plan
Portland Japanese Garden ©
Portland Japanese Garden
Multnomah Falls ©
Multnomah Falls
Powell's City of Books ©
Powell's City of Books

2
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. Kick off your visit on the 15th (Thu): take in the dramatic natural features at Haystack Rock, admire the majestic nature at Hug Point State Park, and then immerse yourself in nature at Ecola State Park. Here are some ideas for day two: admire the majestic nature at Oswald West State Park.

To find ratings, reviews, traveler tips, and more tourist information, go to the Cannon Beach day trip site .

You can drive from Portland to Cannon Beach in 2 hours. Alternatively, you can take a bus. Traveling from Portland in August, things will get slightly colder in Cannon Beach: highs are around 71°F and lows about 55°F. Finish your sightseeing early on the 16th (Fri) so you can drive to Hood River.

Things to do in Cannon Beach

Parks Nature Beaches
Highlights from your plan
Ecola State Park ©
Ecola State Park
Oswald West State Park ©
Oswald West State Park
Hug Point State Park ©
Hug Point State Park

1
night
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. Kick off your visit on the 17th (Sat): take in the dramatic scenery at Starvation Creek State Park and then explore the activities along Columbia River Gorge National Scenic Area.

For where to stay, ratings, traveler tips, and tourist information, go to the Hood River trip planner .

You can drive from Cannon Beach to Hood River in 3 hours. Other options are to take a bus; or do a combination of bus and train. Traveling from Cannon Beach in August, expect nights in Hood River to be about the same, around 60°F, while days are a bit warmer, around 81°F. Cap off your sightseeing on the 17th (Sat) early enough to travel to Redmond.

Things to do in Hood River

Wildlife Parks Nature

Side Trips

Columbia River Gorge National Scenic Area, Starvation Creek State Park
Highlights from your plan
Starvation Creek State Park ©
Starvation Creek State Park

1
night
Redmond

Redmond ©
Redmond is a city in Deschutes County, Oregon, United States. To find more things to do, reviews, ratings, and tourist information, read our Redmond trip builder site .

Drive from Hood River to Redmond in 2.5 hours. Expect a bit warmer weather when traveling from Hood River in August: highs in Redmond hover around 87°F, while lows dip to 48°F. On the 18th (Sun), wrap the sightseeing up by early afternoon so you can travel to Crater Lake National Park.

Things to do in Redmond

Parks Nature
Highlights from your plan
Smith Rock State Park ©
Smith Rock State Park

3
nights
Crater Lake National Park

Crater Lake National Park ©
Reaching a depth of 592 m (1,943 ft), Crater Lake is the deepest lake in the United States.
On the 18th (Sun), hike along Pinnacles Trail and then identify plant and animal life at Rogue River Gorge Viewpoint. On the 19th (Mon), you'll have a packed day of sightseeing: explore the striking landscape of Crater Lake National Park.

To find where to stay, more things to do, photos, and other tourist information, read Crater Lake National Park road trip planner.

Getting from Redmond to Crater Lake National Park by car takes about 3 hours. In August, Crater Lake National Park is somewhat warmer than Redmond - with highs of 93°F and lows of 60°F. You'll have a few hours on the 21st (Wed) to wrap things up before traveling home.

Things to do in Crater Lake National Park

Parks Nature Outdoors

Side Trip

Rogue River Gorge Viewpoint
Highlights from your plan
Crater Lake National Park ©
Crater Lake National Park
Rim Dr ©
Rim Dr
Rogue River Gorge Viewpoint ©
Rogue River Gorge Viewpoint

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