14 days in Oregon Itinerary
Created using Klarna Trips Oregon travel route planner
Start: Toronto
Drive
1
Hood River
— 4 nights
Drive
2
Portland
— 3 nights
Drive
3
Newport
— 2 nights
Drive
4
Cannon Beach
— 2 nights
Fly
End: Toronto
Fri, Feb 10 - Thu, Feb 23
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Hood River — 4 nights
Do some cultural sightseeing at Timberline Lodge and Ski Area and Columbia Gorge Discovery Center & Museum. Museum-lovers will appreciate Fort Dalles Museum and Anderson Homestead and Fire Museum in City Hall. Change things up with these side-trips from Hood River: Mt Hood Cultural Center and Museum (in Government Camp), Cascade Cliffs Vineyard & Winery (in Wishram) and Goldendale (Stonehenge Memorial & Maryhill Winery).
For reviews, other places to visit, traveler tips, and more tourist information, read Hood River trip builder app.
Toronto, Canada to Hood River is an approximately 38-hour car ride. The time zone difference moving from Eastern Standard Time (EST) to Pacific Standard Time (PST) is minus 3 hours. Traveling from Toronto in February, expect Hood River to be somewhat warmer, temps between 9°C and 3°C. Finish your sightseeing early on the 15th (Wed) so you can drive to Portland.
more
For reviews, other places to visit, traveler tips, and more tourist information, read Hood River trip builder app.
Toronto, Canada to Hood River is an approximately 38-hour car ride. The time zone difference moving from Eastern Standard Time (EST) to Pacific Standard Time (PST) is minus 3 hours. Traveling from Toronto in February, expect Hood River to be somewhat warmer, temps between 9°C and 3°C. Finish your sightseeing early on the 15th (Wed) so you can drive to Portland.
Side Trips
The Dalles, Government Camp, Goldendale, Columbia River Gorge National Scenic Area, Cascade Cliffs Vineyard & Winery
Find places to stay Feb 11 — 15:
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Portland — 3 nights

City of Roses
For shopping fun, head to Powell's City of Books or Northwest (Nob Hill). Do some cultural sightseeing at Live Laugh Love Art and Wine Tours & Tastings. There's much more to do: examine the collection at Portland Art Museum, contemplate the long history of Fort Vancouver | National Historic Site, learn the secrets of beer at a beer tour and tasting, and take in nature's colorful creations at Lan Su Chinese Garden.
For more things to do, traveler tips, other places to visit, and other tourist information, go to the Portland route builder app.
Drive from Hood River to Portland in 1.5 hours. Alternatively, you can drive; or take a bus; or take a train. In February in Portland, expect temperatures between 12°C during the day and 3°C at night. Wrap up your sightseeing on the 18th (Sat) early enough to drive to Newport.
more
For more things to do, traveler tips, other places to visit, and other tourist information, go to the Portland route builder app.
Drive from Hood River to Portland in 1.5 hours. Alternatively, you can drive; or take a bus; or take a train. In February in Portland, expect temperatures between 12°C during the day and 3°C at night. Wrap up your sightseeing on the 18th (Sat) early enough to drive to Newport.
Side Trips
Find places to stay Feb 15 — 18:
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Highlights from your trip
Newport — 2 nights
Kick off your visit on the 19th (Sun): get curious at Hatfield Marine Science Center, enjoy the sea views from Yaquina Head Lighthouse, then take in the exciting artwork at Lincoln City Glass Center, and finally stroll around Whale Park. On the 20th (Mon), you'll have a packed day of sightseeing: take a leisurely stroll along Newport's Historic Bayfront, stop by The Kite Company, visit a coastal fixture at Heceta Head Lighthouse, then take in the waterfront at Yachats coastline, and finally appreciate the history behind Bazalgette the Whale at Whale Park.
To find photos, more things to do, where to stay, and more tourist information, read our Newport trip itinerary builder.
Getting from Portland to Newport by car takes about 2.5 hours. Other options: drive; or take a bus; or do a combination of train and bus. In February, daytime highs in Newport are 12°C, while nighttime lows are 5°C. Wrap up your sightseeing on the 20th (Mon) early enough to drive to Cannon Beach.
more
To find photos, more things to do, where to stay, and more tourist information, read our Newport trip itinerary builder.
Getting from Portland to Newport by car takes about 2.5 hours. Other options: drive; or take a bus; or do a combination of train and bus. In February, daytime highs in Newport are 12°C, while nighttime lows are 5°C. Wrap up your sightseeing on the 20th (Mon) early enough to drive to Cannon Beach.
Side Trips
Find places to stay Feb 18 — 20:
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Cannon Beach — 2 nights
Start off your visit on the 21st (Tue): immerse yourself in nature at Ecola State Park, then explore the striking landscape at Haystack Rock, then stroll through Cannon Beach, and finally get a taste of the local shopping with Cannon Beach Gallery. Get ready for a full day of sightseeing on the 22nd (Wed): hike along Cedar Wetlands Preserve, stop by Blue Heron Cheese & Wine Company, then see the interesting displays at Tillamook Air Museum, and finally identify plant and animal life at Nevor Shellfish Farm.
For maps, more things to do, traveler tips, and tourist information, you can read our Cannon Beach vacation planning website.
Drive from Newport to Cannon Beach in 3 hours. Alternatively, you can take a bus. In February, daily temperatures in Cannon Beach can reach 12°C, while at night they dip to 4°C. Finish up your sightseeing early on the 22nd (Wed) so you can catch the flight back home.
more
For maps, more things to do, traveler tips, and tourist information, you can read our Cannon Beach vacation planning website.
Drive from Newport to Cannon Beach in 3 hours. Alternatively, you can take a bus. In February, daily temperatures in Cannon Beach can reach 12°C, while at night they dip to 4°C. Finish up your sightseeing early on the 22nd (Wed) so you can catch the flight back home.
Side Trips
Find places to stay Feb 20 — 22:
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Highlights from your trip
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Oregon travel guide
A land of many faces, Oregon is at once a state of rugged rocky coastlines and deep forests, as well as vibrant cities and small towns packed with award-winning restaurants and trendy shops. With nearly half of its land covered by dense fir, redwood, and pine forests, the state protects varied plant and animal life inside three national parks. In addition to pristine waterfalls, beaches, and lakes perfect for a holiday in nature, Oregon also offers numerous urban tourist attractions. Portland, the state's largest metropolis, notably includes more breweries than any other city in the world, and its central location makes it an ideal base for day trips to Oregon's emerging wine region and many parks.