15 days in Oregon Itinerary

15 days in Oregon Itinerary

Created using Inspirock Oregon travel planner

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Route & dates

15 days in Oregon Itinerary

Start: Winnipeg
Fly + Drive:  9​h 45​min
1
Hood River
— 4 nights
Drive:  3​h
2
Cannon Beach
— 4 nights
Drive:  1​h 30​min
3
Portland
— 6 nights
Fly:  8​h
End: Winnipeg

4
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. Escape the urban bustle at Timberline Lodge and Ski Area and Mt. Hood National Forest. Satisfy your inner culture vulture at Western Antique Aeroplane & Automobile Museum and Springhouse Cellar. Step out of Hood River with an excursion to Fire Museum in City Hall in The Dalles--about 36 minutes away. And it doesn't end there: explore the activities along Columbia River Gorge National Scenic Area, contemplate the geological forces at Mount Hood, see the interesting displays at Columbia Gorge Discovery Center & Museum, and view the masterpieces at Art on Oak.

For where to stay, ratings, photos, and other tourist information, read Hood River trip planner .

Winnipeg, Canada to Hood River is an approximately 10-hour flight. You can also drive. You'll gain 2 hours traveling from Winnipeg to Hood River due to the time zone difference. Traveling from Winnipeg in September, expect somewhat warmer with lows of 16°C in Hood River. Finish up your sightseeing early on the 1st (Tue) so you can go by car to Cannon Beach.

Things to do in Hood River

Nature Parks Outdoors

Side Trips

The Dalles, Starvation Creek State Park, Columbia River Gorge National Scenic Area, Timberline Lodge and Ski Area, Mt. Hood National Forest
Highlights from your plan

4
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. Your cultural itinerary includes sights like Fort Clatsop National Memorial and Lightship Columbia. We've included these beaches for you: Cannon Beach and Haystack Rock. Explore Cannon Beach's surroundings by going to Astoria (Astoria Column & Columbia River Maritime Museum) and Rockaway Beach Wayside (in Rockaway Beach). There's much more to do: immerse yourself in nature at Ecola State Park, see the interesting displays at Seaside Inverted Experience, appreciate the history behind Seaside Beach Lewis and Clark Monument, and kick back and relax at Manzanita Beach.

For more things to do, ratings, photos, and other tourist information, go to the Cannon Beach attractions planner .

Traveling by car from Hood River to Cannon Beach takes 3 hours. Alternatively, you can take a bus; or do a combination of train and bus. October in Cannon Beach sees daily highs of 20°C and lows of 10°C at night. Finish up your sightseeing early on the 5th (Sat) so you can go by car to Portland.

Things to do in Cannon Beach

Parks Nature Outdoors

Side Trips

Astoria, Seaside, Manzanita Beach, Rockaway Beach Wayside
Highlights from your plan
Cannon Beach ©
Cannon Beach
Haystack Rock ©
Haystack Rock
Ecola State Park ©
Ecola State Park

6
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.
Visiting Sokol Blosser Winery and Hyland Forest Park will get you outdoors. Get some cultural insight at Evergreen Aviation & Space Museum and Oregon Museum of Science and Industry. You'll find plenty of places to visit near Portland: Domaine Serene (in Dayton), Willamette Valley Vineyards (in Turner) and The Historic Carousel and Museum (in Albany). And it doesn't end there: contemplate the long history of Pittock Mansion, take in the dramatic scenery at Multnomah Falls, stop by Powell's City of Books, and take a stroll through Ladd's Addition.

To see ratings, photos, traveler tips, and other tourist information, refer to the Portland driving holiday app .

Getting from Cannon Beach to Portland by car takes about 1.5 hours. Other options: take a bus. In October, plan for daily highs up to 22°C, and evening lows to 11°C. Wrap up your sightseeing by early afternoon on the 11th (Fri) to allow enough time to travel back home.

Things to do in Portland

Wineries Museums Parks

Side Trips

McMinnville, Domaine Serene, Carlton Winemakers Studio, The Historic Carousel and Museum, Keeler Estate Vineyard
Highlights from your plan
Portland Japanese Garden ©
Portland Japanese Garden
Multnomah Falls ©
Multnomah Falls
Sokol Blosser Winery ©
Sokol Blosser Winery

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