9 days in Oregon Itinerary

9 days in Oregon Itinerary

Created using Inspirock Oregon trip itinerary builder

Plan created by another user. Make it yours
Fly
1
Portland
— 3 nights
Drive
2
Cannon Beach
— 2 nights
Drive
3
Hood River
— 3 nights
Fly

S M T W T F S
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30
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2
3
4
5
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8
9
10
11
12
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14
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3
nights
Portland

City of Roses

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.
Explore the numerous day-trip ideas around Portland: Multnomah Falls (in Bridal Veil) and Evergreen Aviation & Space Museum (in McMinnville). The adventure continues: admire the natural beauty at Portland Japanese Garden, admire the landmark architecture of Pittock Mansion, get to know the resident critters at Oregon Zoo, and stroll around Tom McCall Waterfront Park.

To find where to stay, maps, ratings, and more tourist information, go to the Portland online trip itinerary planner.

Chicago to Portland is an approximately 7.5-hour flight. You can also drive; or take a train. Traveling from Chicago to Portland, you'll gain 2 hours due to the time zone difference. In October, daytime highs in Portland are 66°F, while nighttime lows are 49°F. Finish your sightseeing early on the 8th (Tue) to allow enough time to drive to Cannon Beach.

Things to do in Portland

Parks · Tours · Wineries · Museums

Side Trips

Highlights from your trip
Powell's City of Books ©
Gift & Specialty Shop
Powell's City of Books
4.8

2
nights
Cannon Beach

Cannon Beach is a city in Clatsop County, Oregon, United States. Kick off your visit on the 9th (Wed): take in the dramatic natural features at Haystack Rock, immerse yourself in nature at Ecola State Park, and then snap pictures at Astoria-Megler Bridge. Keep things going the next day: examine the collection at Seaside Inverted Experience, pause for some photo ops at Astoria Column, then pick up some new knowledge with Columbia River Maritime Museum, and finally stroll through Cannon Beach.

To see photos, reviews, traveler tips, and other tourist information, you can read our Cannon Beach day trip planning website.

You can drive from Portland to Cannon Beach in 1.5 hours. Alternatively, you can take a bus. In October, plan for daily highs up to 63°F, and evening lows to 48°F. Wrap up your sightseeing on the 10th (Thu) early enough to drive to Hood River.

Things to do in Cannon Beach

Parks · Nature · Beaches · Outdoors

Side Trips

Highlights from your trip
Haystack Rock ©
Geologic Formation
Haystack Rock
4.8
Cannon Beach ©
Beach
Cannon Beach
4.8
Columbia River Maritime Museum ©
Lesson / Workshop
Columbia River Maritime Museum
4.8

3
nights
Hood River

The city of Hood River is the seat of Hood River County, Oregon, United States. Kick off your visit on the 11th (Fri): examine the collection at Western Antique Aeroplane & Automobile Museum, contemplate the waterfront views at Columbia River Gorge National Scenic Area, and then take in the views from Bridge of the Gods. Get ready for a full day of sightseeing on the 12th (Sat): fly down the slopes at Timberline Lodge and Ski Area and then trek along Historic Columbia River Highway State Trail.

For photos, more things to do, reviews, and other tourist information, use the Hood River trip itinerary maker site.

Traveling by car from Cannon Beach to Hood River takes 3 hours. Alternatively, you can take a bus; or do a combination of bus and train. In October, daily temperatures in Hood River can reach 67°F, while at night they dip to 45°F. Wrap up your sightseeing by early afternoon on the 13th (Sun) to allow time for travel back home.

Things to do in Hood River

Parks · Nature · Wildlife · Museums

Side Trips

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