12 days in Oregon Itinerary

12 days in Oregon Itinerary

Created using Inspirock Oregon travel planner

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Route & dates

12 days in Oregon Itinerary

Start: Chicago
Fly:  6​h 45​min
1
Portland
— 2 nights
Drive:  3​h 30​min
2
Bend
— 2 nights
Drive:  2​h 45​min
3
Crater Lake National Park
— 2 nights
Drive:  5​h 45​min
4
Newport
— 2 nights
Drive:  2​h 45​min
5
Cannon Beach
— 2 nights
+2
bus + tram + 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.
Kick off your visit on the 26th (Sun): look for gifts at Powell's City of Books, then admire the natural beauty at International Rose Test Garden, then delve into the lush surroundings at Camassia Natural Area, and finally admire the sheer force of Silver Falls State Park. Get ready for a full day of sightseeing on the next day: explore the activities along Columbia River Gorge National Scenic Area.

For reviews, traveler tips, ratings, and tourist information, go to the Portland holiday planner .

Chicago to Portland is an approximately 7-hour flight. You can also drive; or take a train. The time zone difference moving from Central Standard Time (CST) to Pacific Standard Time (PST) is minus 2 hours. Traveling from Chicago in July, Portland is slightly colder at night with lows of 59°F. On the 28th (Tue), you'll travel to Bend.

Things to do in Portland

Parks Nature Wildlife

Side Trips

Camassia Natural Area, Silver Falls State Park, Columbia River Gorge National Scenic Area
Highlights from your plan
Silver Falls State Park ©
Silver Falls State Park
Powell's City of Books ©
Powell's City of Books

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 28th (Tue), take a peaceful walk through Shevlin Park. Get ready for a full day of sightseeing on the next day: trek along Peterson Ridge Trail, then wander the streets of City of Sisters, then view the masterpieces at The Art of Alfred A. Dolezal Gallery, and finally trek along Deschutes River Trail.

To find traveler tips, reviews, maps, and more tourist information, refer to the Bend route planning site .

You can drive from Portland to Bend in 3.5 hours. Other options are to fly; or take a bus. Traveling from Portland in July, plan for little chillier nights in Bend, with lows around 52°F. Wrap up your sightseeing on the 30th (Thu) early enough to drive to Crater Lake National Park.

Things to do in Bend

Parks Trails Outdoors

Side Trips

Sisters, The Art of Alfred A. Dolezal Gallery
Highlights from your plan
Pilot Butte State Scenic Viewpoint ©
City of Sisters ©
City of Sisters
The Art of Alfred A. Dolezal Gallery ©

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.
Kick off your visit on the 31st (Fri): trek along Annie Creek Canyon, then trek along Pinnacles Trail, then hike along Castle Crest Wildflower Trail, and finally take in the awesome beauty at Watchman Peak. Get ready for a full day of sightseeing on the 1st (Sat): take in the dramatic scenery at National Creek Falls and then take in the dramatic scenery at Whitehorse Falls.

To find ratings, photos, traveler tips, and more tourist information, read Crater Lake National Park road trip tool .

Getting from Bend to Crater Lake National Park by car takes about 3 hours. Other options: do a combination of bus and taxi. Expect a bit warmer temperatures when traveling from Bend in July; daily highs in Crater Lake National Park reach 94°F and lows reach 61°F. Finish your sightseeing early on the 1st (Sat) so you can drive to Newport.

Things to do in Crater Lake National Park

Parks Trails Outdoors

Side Trip

National Creek Falls
Highlights from your plan
Annie Creek Canyon ©
Annie Creek Canyon
Watchman Peak ©
Watchman Peak
Castle Crest Wildflower Trail ©
Castle Crest Wildflower Trail

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 2nd (Sun), pick up some local products at Newport Farmer's Market, then look for gifts at Oregon Oyster Farms, then trek along Ocean to Bay Trail, and finally hike along Drift Creek Falls Trail.

To see maps, other places to visit, and more tourist information, use the Newport trip planner .

Drive from Crater Lake National Park to Newport in 6 hours. Alternatively, you can do a combination of car, flight, and bus; or do a combination of taxi, train, and bus. When traveling from Crater Lake National Park in August, plan for cooler days in Newport, with highs around 64°F, while nights are little chillier with lows around 51°F. Wrap up your sightseeing by early afternoon on the 3rd (Mon) to allow time for the car ride to Cannon Beach.

Things to do in Newport

Parks Outdoors Trails

Side Trip

Drift Creek Falls Trail
Highlights from your plan
Nye Beach ©
Nye Beach

2
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. Start off your visit on the 3rd (Mon): immerse yourself in nature at Tolovana Beach State Recreation Site. Here are some ideas for day two: explore the striking landscape at Haystack Rock, then tour the pleasant surroundings at Cannon Beach, and then kick back and relax at Rockaway Beach Wayside.

To see traveler tips, maps, where to stay, and tourist information, go to the Cannon Beach holiday maker tool .

Drive from Newport to Cannon Beach in 3 hours. Alternatively, you can take a bus. While traveling from Newport, expect somewhat warmer days and about the same nights in Cannon Beach, ranging from highs of 71°F to lows of 55°F. Wrap up your sightseeing on the 5th (Wed) early enough to travel back home.

Things to do in Cannon Beach

Parks Outdoors Beaches

Side Trips

Astoria, Rockaway Beach Wayside
Highlights from your plan
Haystack Rock ©
Haystack Rock
Rockaway Beach Wayside ©
Rockaway Beach Wayside
Astoria Oregon Riverwalk ©
Astoria Oregon Riverwalk

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