8 days in Oregon Itinerary

8 days in Oregon Itinerary

Created using Inspirock Oregon route planner

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Route & dates

8 days in Oregon Itinerary

Start: Pierre
Fly + Drive:  12​h
1
Hood River
— 2 nights
Bus:  1​h 15​min
2
Portland
— 3 nights
Drive:  2​h
3
Cannon Beach
— 1 night
Drive + Fly:  12​h 30​min
End: Pierre

2
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. Start off your visit on the 13th (Sun): examine the collection at Western Antique Aeroplane & Automobile Museum, learn about winemaking at Phelps Creek Vineyards, and then explore the activities along Columbia River Gorge National Scenic Area.

Plan my trip to Hood River with suggested itineraries provided by Inspirock.

Pierre to Hood River is an approximately 12-hour flight. You can also drive. The time zone difference when traveling from Pierre to Hood River is minus 2 hours. While traveling from Pierre, expect slightly colder days and about the same nights in Hood River, ranging from highs of 64°F to lows of 48°F. Finish your sightseeing early on the 14th (Mon) so you can drive to Portland.

Things to do in Hood River

Nature Wildlife Parks

Side Trip

Columbia River Gorge National Scenic Area
Highlights from your plan
Phelps Creek Vineyards ©
Phelps Creek Vineyards

3
nights
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.
Popular historic sites such as Pittock Mansion and Eastbank Esplanade are in your itinerary. Take a break from the city and head to Multnomah Falls and Sokol Blosser Winery. Change things up with a short trip to Evergreen Aviation & Space Museum in McMinnville (about 56 minutes away). There's still lots to do: admire the natural beauty at Portland Japanese Garden, see the interesting displays at Oregon Museum of Science and Industry, stop by Powell's City of Books, and make a trip to Pioneer Courthouse Square.

To see where to stay, reviews, photos, and tourist information, go to the Portland trip site .

You can drive from Hood River to Portland in 1.5 hours. Other options are to take a bus; or take a train. When traveling from Hood River in May, plan for a bit warmer days and about the same nights in Portland: temperatures range from 70°F by day to 51°F at night. Finish your sightseeing early on the 17th (Thu) to allow enough time to drive to Cannon Beach.

Things to do in Portland

Parks Museums Nature

Side Trips

Multnomah Falls, Sokol Blosser Winery, Evergreen Aviation & Space Museum
Highlights from your plan
Evergreen Aviation & Space Museum ©
Evergreen Aviation & Space Museum
Multnomah Falls ©
Multnomah Falls
Sokol Blosser Winery ©
Sokol Blosser Winery

1
night
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. On the 17th (Thu), stroll through Cannon Beach and then take in the dramatic natural features at Haystack Rock. Get ready for a full day of sightseeing on the 18th (Fri): explore the striking landscape of Fort Clatsop National Memorial.

To see more things to do, other places to visit, ratings, and more tourist information, use the Cannon Beach road trip planning app .

Traveling by car from Portland to Cannon Beach takes 2 hours. Alternatively, you can take a bus. Traveling from Portland in May, expect nights in Cannon Beach to be about the same, around 47°F, while days are a bit cooler, around 61°F. Finish your sightseeing early on the 18th (Fri) so you can travel back home.

Things to do in Cannon Beach

Parks Nature Historic Sites

Side Trip

Fort Clatsop National Memorial
Highlights from your plan
Haystack Rock ©
Haystack Rock
Cannon Beach ©
Cannon Beach
Fort Clatsop National Memorial ©
Fort Clatsop National Memorial

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