14 days in Oregon Itinerary

14 days in Oregon Itinerary

Created using Inspirock Oregon travel planner

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Route & dates

14 days in Oregon Itinerary

Start: Los Angeles
Fly:  4​h 30​min
1
Portland
— 4 nights
Drive:  1​h 30​min
2
Cannon Beach
— 3 nights
Drive:  3​h
3
Hood River
— 1 night
Drive:  3​h 15​min
4
Bend
— 2 nights
Drive:  4​h 30​min
5
Ashland
— 3 nights
bus + Fly:  5​h 30​min
End: Los Angeles

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.
Attractions like Oregon Museum of Science and Industry and Oregon Zoo make great kid-friendly stops. Step out of the city life by going to Multnomah Falls and Steigerwald Lake National Wildlife Refuge. Explore the numerous day-trip ideas around Portland: Evergreen Aviation & Space Museum (in McMinnville), Opal Creek Wilderness Area (in Salem) and Multnomah Falls (in Troutdale). There's still lots to do: steep yourself in history at Pittock Mansion, admire the natural beauty at International Rose Test Garden, stroll around Hyland Forest Park, and identify plant and animal life at Oaks Bottom Wildlife Refuge.

To find more things to do, ratings, and more tourist information, use the Portland trip itinerary maker site .

Los Angeles to Portland is an approximately 4.5-hour flight. You can also do a combination of bus and flight; or drive. Traveling from Los Angeles in July, expect a bit cooler with lows of 59°F in Portland. Wrap up your sightseeing on the 23rd (Tue) to allow time to drive to Cannon Beach.

Things to do in Portland

Parks Wildlife Outdoors

Side Trips

Hyland Forest Park, Evergreen Aviation & Space Museum, Multnomah Falls, Opal Creek Wilderness Area, Steigerwald Lake National Wildlife Refuge
Highlights from your plan
Evergreen Aviation & Space Museum ©
Evergreen Aviation & Space Museum
Multnomah Falls ©
Multnomah Falls
Oregon Museum of Science and Industry ©

3
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. You'll get in some beach time at Cannon Beach and Haystack Rock. Get in touch with nature at Ecola State Park and Oswald West State Park. Explore Cannon Beach's surroundings by going to Astoria (Columbia River Maritime Museum & Astoria Column). The adventure continues: admire the majestic nature at Hug Point State Park, view the masterpieces at Bronze Coast Gallery, visit a coastal fixture at Tillamook Rock Light, and enjoy the sand and surf at Tolovana Beach State Recreation Site.

To see maps, ratings, where to stay, and more tourist information, read Cannon Beach day trip website .

Traveling by car from Portland to Cannon Beach takes 1.5 hours. Alternatively, you can take a bus. While traveling from Portland, expect little chillier days and about the same nights in Cannon Beach, ranging from highs of 69°F to lows of 55°F. Finish up your sightseeing early on the 26th (Fri) so you can go by car to Hood River.

Things to do in Cannon Beach

Parks Nature Beaches

Side Trip

Astoria
Highlights from your plan
Haystack Rock ©
Haystack Rock
Cannon Beach ©
Cannon Beach
Ecola State Park ©
Ecola State Park

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 (Sat): see the interesting displays at Columbia Gorge Discovery Center & Museum, do a tasting at Marchesi Vineyards, then see the interesting displays at Western Antique Aeroplane & Automobile Museum, and finally take in the exciting artwork at Art on Oak.

To see more things to do, maps, reviews, and more tourist information, read Hood River road trip planning 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. When traveling from Cannon Beach in July, plan for somewhat warmer days and about the same nights in Hood River: temperatures range from 79°F by day to 58°F at night. Finish up your sightseeing early on the 27th (Sat) so you can go by car to Bend.

Things to do in Hood River

Museums Wineries Shopping

Side Trip

Columbia Gorge Discovery Center & Museum
Highlights from your plan
Art on Oak ©
Art on Oak

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.
Start off your visit on the 28th (Sun): take an in-depth tour of High Desert Museum and then admire the majestic nature at Smith Rock State Park. On the 29th (Mon), you'll have a packed day of sightseeing: contemplate the geological forces at Newberry National Volcanic Monument, view the masterpieces at Artists Gallery Sunriver, and then let the river carry you with a rafting and tubing tour.

To find reviews, other places to visit, and tourist information, go to the Bend trip itinerary builder app .

Traveling by car from Hood River to Bend takes 3.5 hours. Alternatively, you can do a combination of bus and flight; or take a bus. When traveling from Hood River in July, plan for a bit warmer days in Bend, with highs around 85°F, while nights are slightly colder with lows around 52°F. Cap off your sightseeing on the 29th (Mon) early enough to go by car to Ashland.

Things to do in Bend

Parks Nature Museums

Side Trips

Artists Gallery Sunriver, Smith Rock State Park
Highlights from your plan
Smith Rock State Park ©
Smith Rock State Park
High Desert Museum ©
High Desert Museum
River Rafting & Tubing

3
nights
Ashland

Ashland is a city in Jackson County, in the State of Oregon. Kick off your visit on the 30th (Tue): get curious at ScienceWorks Hands-on Museum, then take in the exciting artwork at Gathering Glass Studio, then walk around Lithia Park, and finally see a show at Oregon Shakespeare Festival. On the 31st (Wed), you'll have a packed day of sightseeing: see the interesting displays at Bear Hotel Artworks Museum, then look for all kinds of wild species at Wildlife Images - Rehabilitation & Education Center, then shop like a local with The Glass Forge, and finally let the river carry you with a rafting and tubing tour.

To see traveler tips, reviews, where to stay, and other tourist information, go to the Ashland travel route builder tool .

Traveling by car from Bend to Ashland takes 4.5 hours. Alternatively, you can do a combination of flight and bus; or take a bus. Prepare for somewhat warmer weather when traveling from Bend in July: high temperatures in Ashland hover around 94°F and lows are around 61°F. On the 1st (Thu), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Ashland

Parks Adventure Outdoors

Side Trips

Grants Pass, Rogue Creamery, Butte Creek Mill
Highlights from your plan
River Rafting & Tubing
ScienceWorks Hands-On Museum ©
ScienceWorks Hands-On Museum
Butte Creek Mill ©
Butte Creek Mill

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