10 days in Oregon Itinerary

10 days in Oregon Itinerary

Created using Inspirock Oregon itinerary builder

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Route & dates

10 days in Oregon Itinerary

Start: Chicago
Fly:  6​h 45​min
1
Portland
— 2 nights
Drive:  2​h
2
Cannon Beach
— 2 nights
Drive:  2​h 45​min
3
Newport
— 2 nights
Drive:  5​h 45​min
4
Crater Lake National Park
— 2 nights
Drive + Fly:  9​h 45​min
End: Chicago

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.
Dedicate the 19th (Mon) to wine at some of the top wineries in the area. The adventure continues: admire the natural beauty at Portland Japanese Garden, steep yourself in history at Pittock Mansion, look for gifts at Powell's City of Books, and tour the pleasant surroundings at Forest Park.

For where to stay, traveler tips, photos, and more tourist information, go to the Portland vacation builder app .

Chicago to Portland is an approximately 7-hour flight. You can also drive; or take a train. Traveling from Chicago to Portland, you'll gain 2 hours due to the time zone difference. Plan for little chillier nights when traveling from Chicago in August since evenings lows in Portland dip to 60°F. Wrap up your sightseeing on the 19th (Mon) to allow time to drive to Cannon Beach.

Things to do in Portland

Tours Parks Trails
Highlights from your plan
Portland Japanese Garden ©
Portland Japanese Garden
International Rose Test Garden ©
International Rose Test Garden
Powell's City of Books ©
Powell's City of Books

2
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. Kick off your visit on the 20th (Tue): immerse yourself in nature at Oswald West State Park, immerse yourself in nature at Ecola State Park, and then visit a coastal fixture at Tillamook Rock Light.

For ratings, maps, more things to do, and tourist information, read Cannon Beach attractions app .

Getting from Portland to Cannon Beach by car takes about 2 hours. Other options: take a bus. Traveling from Portland in August, expect Cannon Beach to be a bit cooler, temps between 71°F and 55°F. Finish up your sightseeing early on the 21st (Wed) so you can go by car to Newport.

Things to do in Cannon Beach

Parks Nature Historic Sites
Highlights from your plan
Ecola State Park ©
Ecola State Park
Oswald West State Park ©
Oswald West State Park
Tillamook Rock Light ©
Tillamook Rock Light

2
nights
Newport

Newport ©
A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
On the 21st (Wed), look for all kinds of wild species at Yaquina Head Outstanding Natural Area, cruise along Cape Perpetua Visitor Center - Siuslaw National Forest, and then take in the dramatic natural features at Thor's Well. Get ready for a full day of sightseeing on the 22nd (Thu): visit a coastal fixture at Yaquina Head Lighthouse, then admire nature's wide array of creatures at Oregon Coast Aquarium, then take in the waterfront at Yachats coastline, and finally make a trip to Yaquina Bay Bridge.

For traveler tips, more things to do, maps, and tourist information, go to the Newport route website .

Traveling by car from Cannon Beach to Newport takes 3 hours. Alternatively, you can take a bus. When traveling from Cannon Beach in August, plan for little chillier days in Newport, with highs around 64°F, while nights are about the same with lows around 51°F. On the 23rd (Fri), wrap the sightseeing up by early afternoon so you can drive to Crater Lake National Park.

Things to do in Newport

Parks Nature Wildlife

Side Trip

Yachats
Highlights from your plan
Yachats coastline ©
Yachats coastline
Yaquina Head Outstanding Natural Area ©

2
nights
Crater Lake National Park

Crater Lake National Park ©
Reaching a depth of 592 m (1,943 ft), Crater Lake is the deepest lake in the United States.
Crater Lake National Park has been added to your itinerary. Kick off your visit on the 27th (Tue): explore the striking landscape of Crater Lake National Park. On your second day here, contemplate the long history of Rim Village Visitor Center, then trek along Cleetwood Cove Trail, and then step off the mainland to explore Wizard Island.

For other places to visit, photos, reviews, and tourist information, use the Crater Lake National Park vacation planner.

You can drive from Hood River to Crater Lake National Park in 6 hours. Other options are to do a combination of bus, flight, and car; or do a combination of bus, flight, and taxi. Traveling from Hood River in August, expect nights in Crater Lake National Park to be about the same, around 60°F, while days are somewhat warmer, around 93°F. Wrap up your sightseeing by early afternoon on the 29th (Thu) to allow enough time to travel back home.

Things to do in Crater Lake National Park

Parks Nature Trails
Highlights from your plan
Crater Lake National Park ©
Crater Lake National Park
Cleetwood Cove Trail ©
Cleetwood Cove Trail
Rim Village Visitor Center ©
Rim Village Visitor Center

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