14 days in Oregon Itinerary

14 days in Oregon Itinerary

Created using Inspirock Oregon tour planner

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Route & dates

14 days in Oregon Itinerary

Start: Dubai
Fly:  19​h 30​min
1
Portland
— 4 nights
bus:  1​h 15​min
2
Hood River
— 3 nights
Drive:  3​h 15​min
3
Bend
— 2 nights
Drive:  5​h 15​min
4
Astoria
— 2 nights
+2
bus + tram + Fly:  21​h
End: Dubai

4
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.
Visit Pittock Mansion and Eastbank Esplanade for their historical value. Take a break from the city and head to Sokol Blosser Winery and Oaks Bottom Wildlife Refuge. Go for a jaunt from Portland to McMinnville to see Evergreen Aviation & Space Museum about 56 minutes away. There's much more to do: stop by Powell's City of Books, admire the natural beauty at Portland Japanese Garden, wander the streets of Northwest (Nob Hill), and examine the collection at Oregon Museum of Science and Industry.

To find maps, reviews, and more tourist information, refer to the Portland road trip app .

Dubai, United Arab Emirates to Portland is an approximately 19.5-hour flight. You can also do a combination of flight and train; or do a combination of flight and bus. The time zone changes from Gulf Standard Time to Pacific Standard Time, which is usually a -12 hour difference. Traveling from Dubai in September, things will get much colder in Portland: highs are around 28°C and lows about 15°C. Finish your sightseeing early on the 19th (Thu) so you can drive to Hood River.

Things to do in Portland

Historic Sites Parks Museums

Side Trips

Sokol Blosser Winery, Columbia River Highway, Evergreen Aviation & Space Museum
Highlights from your plan
Powell's City of Books ©
Powell's City of Books
Evergreen Aviation & Space Museum ©
Evergreen Aviation & Space Museum
Pittock Mansion ©
Pittock Mansion

3
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. Museum-lovers will appreciate Columbia Gorge Discovery Center & Museum and Fort Dalles Museum and Anderson Homestead. Get outdoors at Timberline Lodge and Ski Area and Columbia River Gorge National Scenic Area. Change things up with these side-trips from Hood River: Multnomah Falls (in Bridal Veil) and Multnomah Falls (in Troutdale). And it doesn't end there: see the interesting displays at Western Antique Aeroplane & Automobile Museum, sample the fine beverages at Hood River Distillers Tasting Room, stroll through Historic Columbia River Highway State Trail, and do a tasting at Marchesi Vineyards.

For more things to do, photos, reviews, and tourist information, read Hood River trip planning site .

Getting from Portland to Hood River by car takes about 1.5 hours. Other options: take a bus; or take a train. Expect little chillier weather when traveling from Portland in September: highs in Hood River hover around 25°C, while lows dip to 16°C. Cap off your sightseeing on the 22nd (Sun) early enough to go by car to Bend.

Things to do in Hood River

Nature Parks Museums

Side Trips

The Dalles, Historic Columbia River Highway State Trail, Multnomah Falls, Timberline Lodge and Ski Area, Multnomah Falls
Highlights from your plan
Multnomah Falls ©
Multnomah Falls
Timberline Lodge and Ski Area ©
Timberline Lodge and Ski Area

2
nights
Bend

Bend ©
An old logging town at the crux of the high desert and ponderosa pine forest, Bend melds a love of the outdoors with cosmopolitan flair.
On the 23rd (Mon), take an in-depth tour of High Desert Museum and then delve into the lush surroundings at Deschutes National Forest. Get ready for a full day of sightseeing on the 24th (Tue): take a memorable drive along McKenzie Pass-Santiam Pass loop, then take a stroll through City of Sisters, and then immerse yourself in nature at Smith Rock State Park.

To see more things to do, where to stay, traveler tips, and more tourist information, refer to the Bend online road trip planner .

Getting from Hood River to Bend by car takes about 3.5 hours. Other options: do a combination of bus and flight; or take a bus. Traveling from Hood River in September, you can expect nighttime temperatures to be slightly colder in Bend, with lows of 7°C. Finish up your sightseeing early on the 24th (Tue) so you can go by car to Astoria.

Things to do in Bend

Parks Nature Museums

Side Trips

Sisters, Smith Rock State Park
Highlights from your plan
Smith Rock State Park ©
Smith Rock State Park
High Desert Museum ©
High Desert Museum
McKenzie Pass-Santiam Pass loop ©
McKenzie Pass-Santiam Pass loop

2
nights
Astoria

Astoria ©
Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
Visit Fort Clatsop National Memorial and The Lewis And Clark National And State Historical Parks for their historical value. Take a break from the city and head to Haystack Rock and Astoria Column. Go for a jaunt from Astoria to Cannon Beach to see Cannon Beach about 44 minutes away. Next up on the itinerary: explore the activities along Columbia River Maritime Museum and see the interesting displays at Seaside Inverted Experience.

For traveler tips, maps, photos, and tourist information, use the Astoria online trip itinerary builder .

You can drive from Bend to Astoria in 5.5 hours. Other options are to do a combination of flight and bus; or take a bus. Expect a bit warmer evenings in Astoria when traveling from Bend in September, with lows around 13°C. Finish your sightseeing early on the 27th (Fri) so you can travel back home.

Things to do in Astoria

Parks Nature Historic Sites

Side Trips

Cannon Beach, Seaside Inverted Experience
Highlights from your plan
Fort Clatsop National Memorial ©
Fort Clatsop National Memorial
Cannon Beach ©
Cannon Beach
Columbia River Maritime Museum ©
Columbia River Maritime Museum

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