16 days in Oregon Itinerary

16 days in Oregon Itinerary

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Route & dates

16 days in Oregon Itinerary

Start: Seattle
train:  3​h 30​min
1
Portland
— 1 night
Fly + Drive:  4​h 30​min
2
Crater Lake National Park
— 1 night
+3
Drive + Fly + Tram + Bus:  7​h 30​min
3
Astoria
— 3 nights
Drive:  2​h
4
Troutdale
— 4 nights
Drive:  45​min
5
Cascade Locks
— 2 nights
Drive:  1​h 30​min
6
Timberline Lodge
— 3 nights
Drive:  2​h 15​min
7
Prineville
— 1 night
train:  3​h 30​min
End: Seattle

1
night
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.
You've now added Sea Lion Caves to your itinerary. On the 23rd (Mon), Head underground at Sea Lion Caves.

To find maps, other places to visit, where to stay, and tourist information, you can read our Portland trip builder tool .

Seattle to Portland is an approximately 3-hour flight. You can also drive; or take a bus. In December, plan for daily highs up to 45°F, and evening lows to 35°F. On the 24th (Tue), you'll travel to Crater Lake National Park.

Things to do in Portland

Parks Nature

Side Trip

Sea Lion Caves
Highlights from your plan
Sea Lion Caves ©
Sea Lion Caves

1
night
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.
For where to stay, traveler tips, and more tourist information, you can read our Crater Lake National Park vacation builder website .

Do a combination of flight and car from Portland to Crater Lake National Park in 4.5 hours. Alternatively, you can drive; or do a combination of flight, bus, and taxi. Expect a daytime high around 46°F in December, and nighttime lows around 32°F. You will leave for Astoria on the 25th (Wed).

Things to do in Crater Lake National Park

Parks Nature Outdoors

3
nights
Astoria

Astoria ©
Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
On the 26th (Thu), take in the dramatic scenery at Wahkeena Falls and then admire the majestic nature at Ecola State Park. On the 27th (Fri), you'll have a packed day of sightseeing: immerse yourself in nature at Bridal Veil Falls and then get some fabulous bargains at Columbia Gorge Premium Outlets.

To see other places to visit, where to stay, maps, and more tourist information, refer to the Astoria travel itinerary planner.

You can do a combination of car, flight, and bus from Crater Lake National Park to Astoria in 7.5 hours. Other options are to drive; or do a combination of taxi, bus, and flight. In December, daytime highs in Astoria are 49°F, while nighttime lows are 37°F. Finish up your sightseeing early on the 28th (Sat) so you can travel to Troutdale.

Things to do in Astoria

Parks Nature Shopping

Side Trips

Troutdale, Bridal Veil Falls, Ecola State Park
Highlights from your plan
Wahkeena Falls ©
Wahkeena Falls
Ecola State Park ©
Ecola State Park
Bridal Veil Falls ©
Bridal Veil Falls

4
nights
Troutdale

Troutdale
Troutdale is a city in Multnomah County, Oregon, U.S.A., north of Gresham and east of Wood Village. To see other places to visit, maps, and tourist information, use the Troutdale online day trip planner .

Getting from Astoria to Troutdale by car takes about 2 hours. December in Troutdale sees daily highs of 45°F and lows of 36°F at night. On the 1st (Wed), you'll travel to Cascade Locks.

Things to do in Troutdale

Parks Outdoors Nature

2
nights
Cascade Locks

Cascade Locks ©
Cascade Locks is a city in Hood River County, Oregon, United States. On the 1st (Wed), take in the views from Bridge of the Gods, then trek along Oneonta Gorge, and then see human ingenuity at work at Bonneville Lock & Dam. On the 2nd (Thu), you'll have a packed day of sightseeing: explore the activities along Sturgeon Viewing Pond and Interpretive Center, walk around Starvation Creek State Park, then identify plant and animal life at Bonneville Hatchery, and finally indulge your thirst for a good beer at Thunder Island Brewing Co.

For other places to visit, ratings, maps, and other tourist information, read our Cascade Locks holiday planner .

You can drive from Troutdale to Cascade Locks in an hour. Expect little chillier temperatures when traveling from Troutdale in January; daily highs in Cascade Locks reach 38°F and lows reach 32°F. Wrap up your sightseeing by early afternoon on the 3rd (Fri) to allow enough time to drive to Timberline Lodge.

Things to do in Cascade Locks

Parks Nature Outdoors

Side Trip

Hood River
Highlights from your plan
Oneonta Gorge ©
Oneonta Gorge
Bonneville Lock & Dam ©
Bonneville Lock & Dam

3
nights
Timberline Lodge

Timberline Lodge ©
Perched high on the south face of one of the most iconic peaks in the Pacific Northwest, Timberline Lodge is the ski and snowboarding area known for the eponymous historic lodge, the design of which emphasizes the area's natural beauty.
On the 3rd (Fri), fly down the slopes at Timberline Lodge and Ski Area. Keep things going the next day: delve into the lush surroundings at Mt. Hood National Forest.

To find photos, ratings, maps, and more tourist information, read our Timberline Lodge online trip itinerary maker .

Getting from Cascade Locks to Timberline Lodge by car takes about 1.5 hours. In January, daytime highs in Timberline Lodge are 38°F, while nighttime lows are 32°F. On the 6th (Mon), you'll travel to Prineville.

Things to do in Timberline Lodge

Nature Parks Historic Sites

Side Trip

Mt. Hood National Forest
Highlights from your plan
Timberline Lodge and Ski Area ©
Timberline Lodge and Ski Area
Mt. Hood National Forest ©
Mt. Hood National Forest

1
night
Prineville

Prineville ©
Prineville is a city in and the county seat of Crook County, Oregon, United States. Your day-by-day itinerary now includes Painted Hills. On the 6th (Mon), cruise along Crooked River Scenic Drive, don't miss a visit to Painted Hills, and then make a trip to Wildland Firefighters Monument. On your second day here, immerse yourself in nature at Prineville Reservoir State Park and then examine the collection at Bowman Museum.

To find maps, photos, other places to visit, and other tourist information, use the Prineville online driving holiday planner .

You can drive from Timberline Lodge to Prineville in 2 hours. Traveling from Timberline Lodge in January, you can expect nighttime temperatures to be a bit cooler in Prineville, with lows of 22°F. Wrap up your sightseeing by early afternoon on the 7th (Tue) to allow enough time to travel back home.

Things to do in Prineville

Parks Nature Outdoors
Highlights from your plan
Painted Hills ©
Painted Hills
Crooked River Scenic Drive ©
Crooked River Scenic Drive
Bowman Museum ©
Bowman Museum

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