30 days in Oregon Itinerary

30 days in Oregon Itinerary

Created using Inspirock Oregon journey planner

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Route & dates

30 days in Oregon Itinerary

Start: Singapore
Fly:  23​h 15​min
1
Bend
— 3 nights
Drive:  2​h 45​min
2
Crater Lake National Park
— 3 nights
Drive:  3​h 45​min
3
Eugene
— 4 nights
Drive:  2​h 15​min
4
Newport
— 4 nights
Drive:  3​h 30​min
5
Astoria
— 4 nights
Drive:  3​h
6
Hood River
— 4 nights
bus:  1​h 15​min
7
Portland
— 5 nights
Fly:  21​h 15​min
End: Singapore

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), Sisters (McKenzie Pass-Santiam Pass loop & Sahalie and Koosah Falls) and Wildland Firefighters Monument (in Prineville). There's much more to do: admire the masterpieces at High Desert Museum, take a stroll through City of Sisters, explore the activities along Deschutes River, and look for gifts at Dudley's Bookshop Cafe.

To see where to stay, ratings, photos, and other tourist information, go to the Bend trip itinerary maker tool .

Singapore, Singapore to Bend is an approximately 23.5-hour flight. Traveling from Singapore to Bend, you'll gain 16 hours due to the time zone difference. Traveling from Singapore in December, things will get much colder in Bend: highs are around 5°C and lows about -6°C. Cap off your sightseeing on the 23rd (Sun) early enough to go by car to Crater Lake National Park.

Things to do in Bend

Parks Nature Museums

Side Trips

Sisters, Wildland Firefighters Monument, Smith Rock State Park
Highlights from your plan
Smith Rock State Park ©
Smith Rock State Park
High Desert Museum ©
High Desert Museum
Deschutes National  Forest ©
Deschutes National Forest

3
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.
Go for a jaunt from Crater Lake National Park to Diamond Lake to see Mount Bailey about 38 minutes away. Spend the 24th (Mon) exploring nature at Crater Lake National Park. There's much more to do: take a memorable drive along Rim Dr, step off the mainland to explore Wizard Island, take in the awesome beauty at Watchman Peak, and steep yourself in history at Rim Village Visitor Center.

For reviews, photos, more things to do, and more tourist information, go to the Crater Lake National Park journey planner .

You can drive from Bend to Crater Lake National Park in 3 hours. Another option is to do a combination of bus and taxi. Traveling from Bend in December, expect Crater Lake National Park to be a bit warmer, temps between 9°C and 0°C. Finish your sightseeing early on the 26th (Wed) so you can drive to Eugene.

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
Mount Bailey ©
Mount Bailey
Rim Dr ©
Rim Dr

4
nights
Eugene

Eugene ©
Eugene is a city of the Pacific Northwest located in the U.S. Change things up with these side-trips from Eugene: Albany (The Historic Carousel and Museum, Albany Regional Museum, & more), The Office Bridge (in Westfir) and Willamette Mountain Mercantile-Oakridge Bike Shop (in Oakridge). The adventure continues: admire all the interesting features of Autzen Stadium, identify plant and animal life at Cascades Raptor Center, explore the landscape on two wheels at Willamette River bike trail, and get lost in a book at Eugene Public Library.

For traveler tips, photos, and tourist information, use the Eugene day trip planning tool .

Drive from Crater Lake National Park to Eugene in 4 hours. Alternatively, you can do a combination of taxi and train. In December in Eugene, expect temperatures between 9°C during the day and 0°C at night. Finish up your sightseeing early on the 30th (Sun) so you can go by car to Newport.

Things to do in Eugene

Parks Shopping Museums

Side Trips

Albany, Willamette Mountain Mercantile-Oakridge Bike Shop, The Official Simpsons Mural, The Office Bridge, Chambers Railroad Bridge
Highlights from your plan
Cascades Raptor Center ©
Cascades Raptor Center
Autzen Stadium ©
Autzen Stadium
The Historic Carousel and Museum ©
The Historic Carousel and Museum

4
nights
Newport

Newport ©
A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
Explore Newport's surroundings by going to Yachats (Yachats coastline, Cape Perpetua Visitor Center - Siuslaw National Forest, & more), Lincoln City Glass Center (in Lincoln City) and Florence (Sandland Adventures, Heceta Head Lighthouse, & more). The adventure continues: admire nature's wide array of creatures at Oregon Coast Aquarium, take a leisurely stroll along Newport's Historic Bayfront, look for all kinds of wild species at Yaquina Head Outstanding Natural Area, and appreciate the history behind Fishermen's Memorial Sanctuary.

For traveler tips, other places to visit, reviews, and tourist information, use the Newport online tour planner .

You can drive from Eugene to Newport in 2.5 hours. Alternatively, you can take a bus. Expect somewhat warmer evenings in Newport when traveling from Eugene in December, with lows around 4°C. Finish your sightseeing early on the 3rd (Thu) so you can drive to Astoria.

Things to do in Newport

Parks Outdoors Fun & Games

Side Trips

Florence, Yachats, Lincoln City Glass Center
Highlights from your plan
Yachats coastline ©
Yachats coastline
Sand Master Park - Sandboarding ©
Sand Master Park - Sandboarding

4
nights
Astoria

Astoria ©
Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
Change things up with these side-trips from Astoria: Cannon Beach (Cannon Beach, Bronze Coast Gallery, & more) and Seaside (Seaside Aquarium & Lewis & Clark Salt Works). There's still lots to do: pause for some photo ops at Astoria Column, explore the activities along Columbia River Maritime Museum, immerse yourself in nature at Fort Stevens State Park, and take in the views from Astoria-Megler Bridge.

To see traveler tips, other places to visit, and more tourist information, you can read our Astoria online trip planner .

Getting from Newport to Astoria by car takes about 3.5 hours. Other options: take a bus. In January, daily temperatures in Astoria can reach 11°C, while at night they dip to 3°C. Wrap up your sightseeing on the 7th (Mon) to allow time to drive to Hood River.

Things to do in Astoria

Parks Nature Beaches

Side Trips

Cannon Beach, Seaside, Neahkahnie Mountain
Highlights from your plan
Haystack Rock ©
Haystack Rock
Ecola State Park ©
Ecola State Park
Cannon Beach ©
Cannon Beach

4
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. You'll find plenty of places to visit near Hood River: The Dalles (The Dalles Murals & Fire Museum in City Hall), Bonneville Lock & Dam (in Cascade Locks) and Multnomah Falls (in Bridal Veil). There's still lots to do: look for all kinds of wild species at Columbia River Gorge National Scenic Area, examine the collection at Western Antique Aeroplane & Automobile Museum, get impressive views of Mount Hood, and learn about all things military at Fort Dalles Museum and Anderson Homestead.

For other places to visit, traveler tips, and tourist information, you can read our Hood River online trip builder .

You can drive from Astoria to Hood River in 3 hours. Alternatively, you can take a bus; or do a combination of bus and train. Prepare for slightly colder weather when traveling from Astoria in January: high temperatures in Hood River hover around 3°C and lows are around 0°C. Wrap up your sightseeing on the 11th (Fri) to allow time to drive to Portland.

Things to do in Hood River

Parks Outdoors Nature

Side Trips

The Dalles, Cascade Locks, Oregon, Summit Ski Area, Multnomah Falls
Highlights from your plan
Multnomah Falls ©
Multnomah Falls

5
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.
Take a break from Portland with a short trip to Evergreen Aviation & Space Museum in McMinnville, about 56 minutes away. Dedicate the 14th (Mon) to wine at some of the top wineries in the area. And it doesn't end there: stop by Powell's City of Books, examine the collection at Oregon Museum of Science and Industry, contemplate the long history of Pittock Mansion, and admire the natural beauty at International Rose Test Garden.

For photos, traveler tips, and other tourist information, read our Portland trip maker site .

You can drive from Hood River to Portland in 1.5 hours. Other options are to take a bus; or take a train. Expect somewhat warmer weather when traveling from Hood River in January: highs in Portland hover around 9°C, while lows dip to 1°C. Cap off your sightseeing on the 16th (Wed) early enough to travel back home.

Things to do in Portland

Tours Museums Parks

Side Trip

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

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