8 days in Oregon Itinerary

8 days in Oregon Itinerary

Created using Inspirock Oregon trip itinerary planner

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Route & dates

8 days in Oregon Itinerary

Start: San Francisco
Fly:  4​h
1
Portland
— 2 nights
Drive:  2​h
2
Astoria
— 2 nights
Drive:  3​h
3
Hood River
— 1 night
Drive:  1​h 15​min
4
Timberline Lodge
— 1 night
Drive:  2​h 30​min
5
Bend
— 1 night
Fly:  4​h 45​min
End: San Francisco

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 some cultural insight at Pittock Mansion and Evergreen Aviation & Space Museum. Step out of the city life by going to Multnomah Falls and Multnomah Falls. Venture out of the city with trips to Carlton Winemakers Studio (in Carlton) and Sokol Blosser Winery (in Dundee). Next up on the itinerary: admire the natural beauty at Portland Japanese Garden, examine the collection at Oregon Museum of Science and Industry, and steep yourself in history at Columbia River Highway.

To see ratings, reviews, maps, and other tourist information, go to the Portland trip builder site .

San Francisco to Portland is an approximately 4-hour flight. You can also do a combination of train and flight; or drive. Traveling from San Francisco in June, expect nights in Portland to be about the same, around 56°F, while days are somewhat warmer, around 77°F. Finish up your sightseeing early on the 24th (Mon) so you can go by car to Astoria.

Things to do in Portland

Parks Museums Nature

Side Trips

Troutdale, Evergreen Aviation & Space Museum, Carlton Winemakers Studio, Sokol Blosser Winery, Multnomah Falls
Highlights from your plan
Portland Japanese Garden ©
Portland Japanese Garden
Multnomah Falls ©
Multnomah Falls
Pittock Mansion ©
Pittock Mansion

2
nights
Astoria

Astoria ©
Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
Kick off your visit on the 25th (Tue): see the interesting displays at Seaside Inverted Experience, kick back and relax at Cannon Beach, then kick back and relax at Haystack Rock, and finally appreciate the history behind Astoria Column. Get ready for a full day of sightseeing on the next day: explore the striking landscape of Fort Clatsop National Memorial.

To see photos, maps, where to stay, and more tourist information, use the Astoria trip itinerary maker tool .

Traveling by car from Portland to Astoria takes 2 hours. Alternatively, you can take a bus; or do a combination of train and bus. When traveling from Portland in June, plan for little chillier days and about the same nights in Astoria: temperatures range from 66°F by day to 52°F at night. Finish your sightseeing early on the 26th (Wed) so you can drive to Hood River.

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
Astoria Column ©
Astoria Column

1
night
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. Start off your visit on the 27th (Thu): explore the activities along Columbia River Gorge National Scenic Area, then examine the collection at Western Antique Aeroplane & Automobile Museum, and then view the masterpieces at Art on Oak.

To find ratings, more things to do, traveler tips, and tourist information, you can read our Hood River trip maker .

Traveling by car from Astoria to Hood River takes 3 hours. Alternatively, you can take a bus; or do a combination of bus and train. Traveling from Astoria in June, you will find days in Hood River are somewhat warmer (72°F), and nights are about the same (55°F). Wrap up your sightseeing on the 27th (Thu) to allow time to drive to Timberline Lodge.

Things to do in Hood River

Wildlife Parks Nature

Side Trip

Columbia River Gorge National Scenic Area
Highlights from your plan
Art on Oak ©
Art on Oak

1
night
Timberline Lodge

Timberline Lodge ©
Perched high on the south face of one of the most iconic peaks in the Pacific Northwest, Timberline Lodge is the ski and snowboarding area known for the eponymous historic lodge, the design of which emphasizes the area's natural beauty.
On the 28th (Fri), delve into the lush surroundings at Mt. Hood National Forest and then fly down the slopes at Timberline Lodge and Ski Area.

Plan trip to Timberline Lodge with our itinerary maker to find out where to go and what to do.

Drive from Hood River to Timberline Lodge in 1.5 hours. Expect a daytime high around 72°F in June, and nighttime lows around 55°F. Wrap up your sightseeing on the 28th (Fri) to allow time to travel to Bend.

Things to do in Timberline Lodge

Nature Winter Sports Historic Sites

Side Trip

Mt. Hood National Forest
Highlights from your plan
Timberline Lodge and Ski Area ©
Timberline Lodge and Ski Area
Mt. Hood National Forest ©
Mt. Hood National Forest

1
night
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 29th (Sat), stop by Artists Gallery Sunriver, then look and learn at Oregon Observatory, and then learn more about the world around you at High Desert Museum.

To see traveler tips, where to stay, reviews, and other tourist information, read our Bend trip planner .

Getting from Timberline Lodge to Bend by car takes about 2.5 hours. Plan for little chillier nights when traveling from Timberline Lodge in June since evenings lows in Bend dip to 45°F. Finish your sightseeing early on the 29th (Sat) to allow enough time to travel back home.

Things to do in Bend

Museums Wildlife Parks

Side Trip

Sunriver
Highlights from your plan
High Desert Museum ©
High Desert Museum
Oregon Observatory ©
Oregon Observatory

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