9 days in Oregon Itinerary

9 days in Oregon Itinerary

Created using Inspirock Oregon tour itinerary builder

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Route & dates

9 days in Oregon Itinerary

Start: Los Angeles
Fly:  4​h 30​min
1
Portland
— 2 nights
Drive:  2​h
2
Cannon Beach
— 2 nights
Drive:  3​h
3
Hood River
— 2 nights
Drive:  1​h 30​min
4
Gresham
— 2 nights
Fly:  5​h
End: Los Angeles

2
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.
Get outdoors at Sokol Blosser Winery and Oregon Zoo. Do some cultural sightseeing at Evergreen Aviation & Space Museum and Portland Art Museum. You'll find plenty of places to visit near Portland: Natalies Estate Winery (in Newberg) and Carlton Winemakers Studio (in Carlton). There's still lots to do: stop by Powell's City of Books, see the interesting displays at Oregon Museum of Science and Industry, admire the natural beauty at International Rose Test Garden, and steep yourself in history at Pittock Mansion.

To find more things to do, traveler tips, reviews, and other tourist information, you can read our Portland travel route planner .

Los Angeles to Portland is an approximately 4.5-hour combination of train and flight. You can also fly; or drive. Traveling from Los Angeles in December, you will find days in Portland are cooler (45°F), and nights are little chillier (35°F). Finish your sightseeing early on the 19th (Wed) so you can drive to Cannon Beach.

Things to do in Portland

Museums Parks Wineries

Side Trips

Natalies Estate Winery, Carlton Winemakers Studio, Evergreen Aviation & Space Museum, Sokol Blosser Winery
Highlights from your plan
Powell's City of Books ©
Powell's City of Books
Evergreen Aviation & Space Museum ©
Evergreen Aviation & Space Museum
Oregon Zoo ©
Oregon Zoo

2
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. Kick off your visit on the 20th (Thu): stroll through Cannon Beach, explore the striking landscape at Haystack Rock, then look for gifts at Bruce's Candy Kitchen, and finally examine the collection at Seaside Inverted Experience. On your second day here, examine the collection at Columbia River Maritime Museum, examine the collection at Flavel House Museum, and then admire the majestic nature at Ecola State Park.

To find traveler tips, photos, maps, and tourist information, go to the Cannon Beach tour builder app .

Traveling by car from Portland to Cannon Beach takes 2 hours. Alternatively, you can take a bus. In December, daytime highs in Cannon Beach are 49°F, while nighttime lows are 37°F. Finish your sightseeing early on the 21st (Fri) to allow enough time to drive to Hood River.

Things to do in Cannon Beach

Parks Nature Beaches

Side Trips

Astoria, Seaside Inverted Experience
Highlights from your plan
Cannon Beach ©
Cannon Beach
Ecola State Park ©
Ecola State Park
Columbia River Maritime Museum ©
Columbia River Maritime Museum

2
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. On the 22nd (Sat), see the interesting displays at Western Antique Aeroplane & Automobile Museum, then do a tasting at Marchesi Vineyards, and then explore the activities along Columbia River Gorge National Scenic Area. On the 23rd (Sun), you'll have a packed day of sightseeing: do a tasting at Maryhill Winery, then learn about winemaking at Sunshine Mill Winery, then see the interesting displays at Columbia Gorge Discovery Center & Museum, and finally indulge your thirst for a good beer at Full Sail Brewing Company.

For other places to visit, more things to do, and other tourist information, go to the Hood River trip builder website .

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. Traveling from Cannon Beach in December, things will get little chillier in Hood River: highs are around 41°F and lows about 30°F. Finish your sightseeing early on the 23rd (Sun) so you can travel to Gresham.

Things to do in Hood River

Wineries Wildlife Nature

Side Trips

The Dalles, Maryhill Winery, Columbia River Gorge National Scenic Area
Highlights from your plan

2
nights
Gresham

Gresham ©
Gresham is a city located in Multnomah County, Oregon, in the United States, immediately east of Portland. On the 24th (Mon), steep yourself in history at Columbia River Highway, then take in the dramatic natural features at Oneonta Gorge, and then admire the striking features of Vista House.

For maps, other places to visit, and other tourist information, you can read our Gresham trip planning site .

Drive from Hood River to Gresham in an hour. Traveling from Hood River in December, expect a bit warmer with lows of 36°F in Gresham. Wrap up your sightseeing by early afternoon on the 25th (Tue) to allow enough time to travel back home.

Things to do in Gresham

Shopping Outdoors Trails

Side Trips

Vista House, Oneonta Gorge, Columbia River Highway, Clackamas Town Center, Terra Casa
Highlights from your plan
Clackamas Town Center ©
Clackamas Town Center
Oneonta Gorge ©
Oneonta Gorge
Vista House ©
Vista House

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