13 days in Oregon Itinerary

13 days in Oregon Itinerary

Created using Inspirock Oregon journey planner

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Route & dates

13 days in Oregon Itinerary

Start: Chicago
Fly:  9​h
1
Bend
— 2 nights
Drive:  2​h 45​min
2
Crater Lake National Park
— 2 nights
Drive:  5​h
3
Florence
— 2 nights
Drive:  1​h 15​min
4
Newport
— 2 nights
Drive:  2​h 45​min
5
Cannon Beach
— 2 nights
Drive:  1​h 30​min
6
Portland
— 2 nights
Fly:  6​h 45​min
End: Chicago

2
nights
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 21st (Tue), let the river carry you with a rafting and tubing tour and then contemplate the waterfront views at North and South Twin Lakes. Here are some ideas for day two: get impressive views of Newberry National Volcanic Monument, then trek along Deschutes River Trail, and then walk around Shevlin Park.

To find photos, where to stay, ratings, and other tourist information, use the Bend trip itinerary planning site .

Chicago to Bend is an approximately 9-hour flight. You can also do a combination of subway, bus, and flight; or drive. Traveling from Chicago to Bend, you'll gain 2 hours due to the time zone difference. Traveling from Chicago in July, you can expect nighttime temperatures to be little chillier in Bend, with lows of 52°F. Finish up your sightseeing early on the 22nd (Wed) so you can go by car to Crater Lake National Park.

Things to do in Bend

Parks Outdoors Nature
Highlights from your plan
River Rafting & Tubing
Newberry National Volcanic Monument ©
North and South Twin Lakes ©
North and South Twin Lakes

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.
On the 23rd (Thu), explore and take pictures at Rim Dr, take in the awesome beauty at Watchman Peak, then tour the pleasant surroundings at Castle Crest Wildflower Trail, and finally trek along Pinnacles Trail. Keep things going the next day: look for all kinds of wild species at Rogue River Gorge Viewpoint, take a memorable drive along Rogue-Umpqua Scenic Byway, then admire the sheer force of National Creek Falls, and finally delve into the lush surroundings at Umpqua National Forest.

To find more things to do, maps, other places to visit, and more tourist information, you can read our Crater Lake National Park tour itinerary planner.

Drive from Bend to Crater Lake National Park in 3 hours. Alternatively, you can 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. Wrap up your sightseeing on the 24th (Fri) early enough to drive to Florence.

Things to do in Crater Lake National Park

Outdoors Parks Scenic Drive

Side Trips

Prospect, Rogue-Umpqua Scenic Byway, Umpqua National Forest
Highlights from your plan
Rim Dr ©
Rim Dr
Rogue River Gorge Viewpoint ©
Rogue River Gorge Viewpoint
Watchman Peak ©
Watchman Peak

2
nights
Florence

Florence ©
Florence is a coastal city in Lane County, in the U.S. Kick off your visit on the 25th (Sat): stroll through Hobbit Trail, then have fun at Sand Master Park, and then kick back and relax at Heceta Beach. On your second day here, view the masterpieces at Backstreet Gallery, try for a hole-in-one at Sandland Adventures, then identify plant and animal life at Dean Creek Elk Viewing Area, and finally take in the dramatic natural features at Thor's Well.

To find more things to do, traveler tips, other places to visit, and more tourist information, you can read our Florence road trip website .

You can drive from Crater Lake National Park to Florence in 5 hours. Another option is to do a combination of taxi, train, and bus. Traveling from Crater Lake National Park in July, expect nights in Florence to be little chillier, around 54°F, while days are much colder, around 67°F. Finish your sightseeing early on the 26th (Sun) to allow enough time to drive to Newport.

Things to do in Florence

Parks Outdoors Fun & Games

Side Trips

Dean Creek Elk Viewing Area, Thor's Well
Highlights from your plan
Sand Master Park - Sandboarding ©
Sand Master Park - Sandboarding
Dean Creek Elk Viewing Area ©
Dean Creek Elk Viewing Area
Heceta Beach ©
Heceta Beach

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.
Start off your visit on the 27th (Mon): admire the majestic nature at Alsea Bay Bridge Interpretive Center, admire the majestic nature at Seal Rock State Wayside, and then enjoy the sand and surf at Nye Beach. On your second day here, browse the fresh offerings at Newport Farmer's Market, take in the waterfront activity at Newport Bay Fishing Pier, look for gifts at Oregon Oyster Farms, then admire the majestic nature at Smelt Sands State Park, and finally immerse yourself in nature at Yachats State Park.

To see other places to visit, reviews, and tourist information, use the Newport trip maker app .

Traveling by car from Florence to Newport takes 1.5 hours. Alternatively, you can take a bus. July in Newport sees daily highs of 63°F and lows of 50°F at night. Finish your sightseeing early on the 28th (Tue) so you can drive to Cannon Beach.

Things to do in Newport

Parks Nature Shopping

Side Trips

Yachats, Seal Rock State Wayside, Alsea Bay Bridge Interpretive Center
Highlights from your plan
Seal Rock State Wayside ©
Seal Rock State Wayside
Nye Beach ©
Nye Beach
Alsea Bay Bridge Interpretive Center ©

2
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. On the 29th (Wed), pause for some photo ops at Seaside Beach Lewis and Clark Monument, appreciate the history behind Astoria Column, then take in the dramatic natural features at Haystack Rock, and finally immerse yourself in nature at Hug Point State Park. Here are some ideas for day two: stop by Bruce's Candy Kitchen, then shop like a local with Icefire Glassworks, and then kick back and relax at Cannon Beach.

Ask Inspirock to suggest an itinerary and make planning a trip to Cannon Beach fast, fun, and easy.

You can drive from Newport to Cannon Beach in 3 hours. Another option is to take a bus. Traveling from Newport in July, you will find days in Cannon Beach are a bit warmer (69°F), and nights are about the same (55°F). Finish your sightseeing early on the 30th (Thu) so you can drive to Portland.

Things to do in Cannon Beach

Parks Outdoors Beaches

Side Trips

Seaside Beach Lewis and Clark Monument, Astoria Column
Highlights from your plan
Haystack Rock ©
Haystack Rock
Hug Point State Park ©
Hug Point State Park
Cannon Beach ©
Cannon Beach

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.
On the 31st (Fri), pick up some local products at Portland Farmers Market - Office Location, stroll through Wintler Community Park, then admire the sheer force of Multnomah Falls, and finally admire the sheer force of Wahkeena Falls.

To see maps, traveler tips, where to stay, and more tourist information, you can read our Portland journey maker .

Traveling by car from Cannon Beach to Portland takes 1.5 hours. Alternatively, you can take a bus. Traveling from Cannon Beach in July, expect nights in Portland to be about the same, around 59°F, while days are a bit warmer, around 83°F. You'll have a few hours on the 1st (Sat) to wrap things up before traveling home.

Things to do in Portland

Parks Nature Shopping

Side Trips

Wintler Community Park, Multnomah Falls, Wahkeena Falls
Highlights from your plan
Wahkeena Falls ©
Wahkeena Falls
Multnomah Falls ©
Multnomah Falls
Powell's City of Books ©
Powell's City of Books

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