19 days in Oregon Itinerary

19 days in Oregon Itinerary

Created using Inspirock Oregon trip planner

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Route & dates

19 days in Oregon Itinerary

Start: San Diego
Fly:  7​h
1
Bend
— 5 nights
Drive:  3​h 15​min
2
Hood River
— 4 nights
Drive:  3​h
3
Astoria
— 4 nights
Drive:  2​h
4
Portland
— 5 nights
Fly:  4​h 30​min
End: San Diego

5
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.
Shop till you drop at The Art of Alfred A. Dolezal Gallery and Artists Gallery Sunriver. Step out of the city life by going to High Desert Museum and Smith Rock State Park. Change things up with these side-trips from Bend: Sisters (Cascade Street Distillery & City of Sisters), Erickson Aircraft Collection (in Madras) and The Museum at Warm Springs (in Warm Springs). The adventure continues: look for all kinds of wild species at Fort Rock State Natural Area, delve into the lush surroundings at Opal Creek Wilderness Area, stroll around Drake Park, and take a stroll through Old Mill District.

To see maps, where to stay, and other tourist information, go to the Bend sightseeing planning site .

San Diego to Bend is an approximately 7-hour flight. You can also do a combination of train and flight; or drive. When traveling from San Diego in April, plan for a bit cooler days and much colder nights in Bend: temperatures range from 58°F by day to 33°F at night. Finish your sightseeing early on the 6th (Mon) to allow enough time to drive to Hood River.

Things to do in Bend

Parks Museums Wildlife

Side Trips

Sisters, Redmond, Erickson Aircraft Collection, Fort Rock State Natural Area, Artists Gallery Sunriver
Highlights from your plan
Smith Rock State Park ©
Smith Rock State Park
High Desert Museum ©
High Desert Museum
Fort Rock State Natural Area ©
Fort Rock State Natural Area

4
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. Get a sense of the local culture at Timberline Lodge and Ski Area and Fort Dalles Museum and Anderson Homestead. Let the collections at Western Antique Aeroplane & Automobile Museum and Fire Museum in City Hall capture your imagination. Step out of Hood River to go to Wasco and see Cottonwood Canyon State Park, which is approximately 1h 30 min away. Next up on the itinerary: explore the activities along Columbia River Gorge National Scenic Area, walk around Port Marina Park, contemplate the geological forces at Mount Hood, and head outdoors with Big Winds.

To see other places to visit, where to stay, photos, and tourist information, read Hood River road trip app .

Traveling by car from Bend to Hood River takes 3.5 hours. Alternatively, you can do a combination of flight and bus; or take a bus. Expect somewhat warmer evenings in Hood River when traveling from Bend in April, with lows around 43°F. Wrap up your sightseeing on the 10th (Fri) early enough to drive to Astoria.

Things to do in Hood River

Parks Nature Outdoors

Side Trips

The Dalles, Cottonwood Canyon State Park, Timberline Lodge and Ski Area, Columbia River Gorge National Scenic Area, Historic Columbia River Highway State Trail
Highlights from your plan

4
nights
Astoria

Astoria ©
Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
Museum-lovers will get to explore Columbia River Maritime Museum and Seaside Inverted Experience. Satisfy your inner culture vulture at Fort Clatsop National Memorial and The Lewis And Clark National And State Historical Parks. You'll find plenty of places to visit near Astoria: Cannon Beach (Haystack Rock, Cannon Beach, & more) and Manzanita Beach (in Manzanita). And it doesn't end there: identify plant and animal life at Astoria Column, immerse yourself in nature at Fort Stevens State Park, and buy something for everyone on your list at Seaside Carousel Mall.

To see traveler tips, reviews, other places to visit, and other tourist information, you can read our Astoria itinerary maker site .

Drive from Hood River to Astoria in 3 hours. Alternatively, you can take a bus; or do a combination of train and bus. April in Astoria sees daily highs of 58°F and lows of 43°F at night. Wrap up your sightseeing on the 14th (Tue) to allow time to drive to Portland.

Things to do in Astoria

Parks Nature Historic Sites

Side Trips

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

5
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.
Do your shopping at Powell's City of Books and Live Laugh Love Art. Your cultural itinerary includes sights like Evergreen Aviation & Space Museum and Portland Art Museum. You'll find plenty of places to visit near Portland: Natalies Estate Winery (in Newberg), Winter's Hill Estate (in Dayton) and Multnomah Falls (in Bridal Veil). Next up on the itinerary: admire the natural beauty at Portland Japanese Garden, see the interesting displays at The Historic Carousel and Museum, browse the eclectic array of goods at Portland Saturday Market, and steep yourself in history at Columbia River Highway.

For ratings, other places to visit, photos, and other tourist information, go to the Portland trip itinerary maker app .

You can drive from Astoria to Portland in 2 hours. Other options are to take a bus; or do a combination of bus and train. In April, daytime highs in Portland are 63°F, while nighttime lows are 45°F. Wrap up your sightseeing on the 19th (Sun) to allow time to travel back home.

Things to do in Portland

Museums Parks Historic Sites

Side Trips

Winter's Hill Estate, Town Center Park, Columbia River Highway, Natalies Estate Winery, Live Laugh Love Art
Highlights from your plan
Powell's City of Books ©
Powell's City of Books
Evergreen Aviation & Space Museum ©
Evergreen Aviation & Space Museum
Multnomah Falls ©
Multnomah Falls

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