20 days in Oregon Itinerary

20 days in Oregon Itinerary

Created using Inspirock United States itinerary planner

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Route & dates

20 days in Oregon Itinerary

Start: Portland
1
Portland
— 3 nights
2
Hood River
— 3 nights
Drive:  3​h 15​min
3
Bend
— 3 nights
Drive:  2​h 45​min
4
Crater Lake National Park
— 2 nights
Drive:  2​h
5
Grants Pass
— 3 nights
Drive:  3​h 45​min
6
Yachats
— 2 nights
Drive:  3​h 15​min
7
Cannon Beach
— 3 nights
Drive:  2​h
End: Portland

3
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.
Explore the numerous day-trip ideas around Portland: Multnomah Falls (in Bridal Veil) and Evergreen Aviation & Space Museum (in McMinnville). Dedicate the 15th (Sat) to wine at some of the top wineries in the area. Next up on the itinerary: admire the natural beauty at Portland Japanese Garden, contemplate the long history of Pittock Mansion, examine the collection at Oregon Museum of Science and Industry, and browse the collection at Multnomah County Central Library.

To find ratings, traveler tips, where to stay, and tourist information, read Portland trip planner .

Use the Route module to see travel options from your home to Portland. In December, daytime highs in Portland are 45°F, while nighttime lows are 35°F. Finish your sightseeing early on the 15th (Sat) to allow enough time to drive to Hood River.

Things to do in Portland

Parks Tours Museums

Side Trips

Multnomah Falls, Evergreen Aviation & Space Museum
Highlights from your plan
Portland Japanese Garden ©
Portland Japanese Garden
Powell's City of Books ©
Powell's City of Books
International Rose Test Garden ©
International Rose Test Garden

3
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. Explore Hood River's surroundings by going to Summit Ski Area (in Government Camp), Timberline Lodge and Ski Area (in Timberline Lodge) and Bonneville Lock & Dam (in Cascade Locks). And it doesn't end there: explore the activities along Columbia River Gorge National Scenic Area, explore and take pictures at Hood River County Fruit Loop, and examine the collection at Western Antique Aeroplane & Automobile Museum.

For traveler tips, reviews, maps, and more tourist information, read our Hood River sightseeing planner.

You can drive from Portland to Hood River in 1.5 hours. Alternatively, you can take a bus; or take a train. Traveling from Portland in December, plan for little chillier nights in Hood River, with lows around 30°F. Cap off your sightseeing on the 18th (Tue) early enough to go by car to Bend.

Things to do in Hood River

Parks Outdoors Nature

Side Trips

Oregon, Bonneville Lock & Dam, Timberline Lodge and Ski Area, Summit Ski Area
Highlights from your plan

3
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.
Explore the numerous day-trip ideas around Bend: Smith Rock State Park (in Redmond) and McKenzie Pass-Santiam Pass loop (in Sisters). Next up on the itinerary: get engrossed in the history at High Desert Museum, indulge your thirst for a good beer at Deschutes Brewery, explore the striking landscape at Balancing Rocks, and test your team's savvy at popular escape rooms.

For where to stay, other places to visit, maps, and more tourist information, you can read our Bend online travel planner .

You can drive from Hood River to Bend in 3.5 hours. Other options are to do a combination of bus and flight; or take a bus. Expect slightly colder evenings in Bend when traveling from Hood River in December, with lows around 22°F. Finish up your sightseeing early on the 21st (Fri) so you can go by car to Crater Lake National Park.

Things to do in Bend

Parks Nature Wildlife

Side Trips

Sisters, Smith Rock State Park
Highlights from your plan
Smith Rock State Park ©
Smith Rock State Park
High Desert Museum ©
High Desert Museum
McKenzie Pass-Santiam Pass loop ©
McKenzie Pass-Santiam Pass loop

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 22nd (Sat), explore the wealth of natural beauty at Crater Lake National Park. Keep things going the next day: take your sightseeing to a higher altitude at Watchman Peak and then hit the slopes at Mount Bailey.

To find more things to do, ratings, and more tourist information, you can read our Crater Lake National Park day trip app .

Drive from Bend to Crater Lake National Park in 3 hours. Alternatively, you can do a combination of bus and taxi. In December, Crater Lake National Park is somewhat warmer than Bend - with highs of 46°F and lows of 32°F. Finish your sightseeing early on the 23rd (Sun) so you can travel to Grants Pass.

Things to do in Crater Lake National Park

Parks Nature Outdoors

Side Trip

Mount Bailey
Highlights from your plan
Crater Lake National Park ©
Crater Lake National Park

3
nights
Grants Pass

Grants Pass ©
Grants Pass is a city in, and the county seat of, Josephine County, Oregon, United States. Get out of town with these interesting Grants Pass side-trips: Medford (JCLS Medford Library, King of the Rogue Outfitters, & more) and Ashland (Oregon Shakespeare Festival & Lithia Park). There's lots more to do: identify plant and animal life at Wildlife Images - Rehabilitation & Education Center, snap pictures at The Wimer Covered Bridge, stop by Rogue Creamery, and view the masterpieces at The Glass Forge.

For ratings, photos, and other tourist information, go to the Grants Pass online holiday planner .

You can drive from Crater Lake National Park to Grants Pass in 2 hours. Traveling from Crater Lake National Park in December, expect nights in Grants Pass to be about the same, around 32°F, while days are slightly colder, around 40°F. Finish your sightseeing early on the 26th (Wed) to allow enough time to travel to Yachats.

Things to do in Grants Pass

Parks Nature Outdoors

Side Trips

Medford, Ashland, The Wimer Covered Bridge, Rogue Creamery
Highlights from your plan
Rogue River ©
Rogue River
Lithia Park ©
Lithia Park

2
nights
Yachats

Yachats ©
Yachats is a small coastal city in Lincoln County, Oregon, United States. On the 27th (Thu), take in the waterfront at Yachats coastline, meet the residents at Oregon Coast Aquarium, then take a leisurely stroll along Newport's Historic Bayfront, and finally take in the views from Yaquina Bay Bridge. On your second day here, take a memorable drive along Cape Perpetua Visitor Center - Siuslaw National Forest, then get in on the excitement at Sand Master Park, and then take in the pleasant sights at Strawberry Hill Wayside.

For where to stay, photos, other places to visit, and tourist information, read our Yachats day trip planning site .

You can drive from Grants Pass to Yachats in 4 hours. Traveling from Grants Pass in December, things will get somewhat warmer in Yachats: highs are around 49°F and lows about 39°F. Finish your sightseeing early on the 28th (Fri) so you can drive to Cannon Beach.

Things to do in Yachats

Parks Outdoors Scenic Drive

Side Trips

Newport, Florence
Highlights from your plan
Yachats coastline ©
Yachats coastline
Sand Master Park ©
Sand Master Park

3
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. Explore Cannon Beach's surroundings by going to Astoria (Fort Stevens State Park, Columbia River Maritime Museum, & more). There's still lots to do: take in the dramatic natural features at Haystack Rock, immerse yourself in nature at Oswald West State Park, enjoy the sand and surf at Cannon Beach, and look for gifts at Cannon Beach Bookstore.

To see where to stay, ratings, traveler tips, and tourist information, refer to the Cannon Beach trip maker .

Traveling by car from Yachats to Cannon Beach takes 3.5 hours. Alternatively, you can take a bus. Expect a daytime high around 49°F in December, and nighttime lows around 37°F. Wrap up your sightseeing on the 31st (Mon) early enough to drive back home.

Things to do in Cannon Beach

Parks Nature Outdoors

Side Trips

Astoria, Seaside Inverted Experience
Highlights from your plan
Haystack Rock ©
Haystack Rock
Ecola State Park ©
Ecola State Park
Cannon Beach ©
Cannon Beach

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