16 days in Oregon Itinerary

16 days in Oregon Itinerary

Created using Inspirock Oregon trip itinerary planner

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Route & dates

16 days in Oregon Itinerary

Start: Pocatello
Fly:  6​h 15​min
1
Portland
— 3 nights
Drive:  1​h 30​min
2
Cannon Beach
— 3 nights
Drive:  3​h 15​min
3
Yachats
— 2 nights
Drive + Bus:  4​h 30​min
4
Bend
— 3 nights
Drive:  3​h
5
The Dalles
— 3 nights
Drive:  7​h 45​min
End: Pocatello

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.
Portland is known for parks, shopping, zoos & aquariums, museums, and nature. Your plan includes some of its best attractions: admire the natural beauty at Portland Japanese Garden, indulge your senses at some of the top wineries in the area, hike along Forest Park, and stop by Powell's City of Books.

To see other places to visit, ratings, photos, and tourist information, you can read our Portland trip planner .

Pocatello to Portland is an approximately 6.5-hour flight. You can also drive. Due to the time zone difference, you'll gain 1 hour traveling from Pocatello to Portland. Traveling from Pocatello in September, Portland is a bit warmer at night with lows of 55°F. Wrap up your sightseeing on the 4th (Fri) to allow time to drive to Cannon Beach.

Things to do in Portland

Parks Tours Zoos & Aquariums
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
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. Get out of town with these interesting Cannon Beach side-trips: Astoria (Astoria Column, Fort Stevens State Park, & more). There's much more to do: explore the striking landscape at Haystack Rock, immerse yourself in nature at Ecola State Park, enjoy the sand and surf at Manzanita Beach, and pause for some photo ops at Seaside Beach Lewis and Clark Monument.

For other places to visit, photos, ratings, and other tourist information, you can read our Cannon Beach trip builder website .

Traveling by car from Portland to Cannon Beach takes 1.5 hours. Alternatively, you can take a bus. Traveling from Portland in September, you will find days in Cannon Beach are little chillier (69°F), and nights are about the same (52°F). Finish up your sightseeing early on the 7th (Mon) so you can go by car to Yachats.

Things to do in Cannon Beach

Parks Nature Beaches

Side Trips

Astoria, Manzanita Beach, Seaside Beach Lewis and Clark Monument
Highlights from your plan
Ecola State Park ©
Ecola State Park
Haystack Rock ©
Haystack Rock
Cannon Beach ©
Cannon Beach

2
nights
Yachats

Yachats ©
Yachats is a small coastal city in Lincoln County, Oregon, United States. Start off your visit on the 8th (Tue): enjoy some diversion at Sand Master Park, cruise along Cape Perpetua Visitor Center - Siuslaw National Forest, and then take in the waterfront at Yachats coastline. Get ready for a full day of sightseeing on the next day: explore and take pictures at Oregon Coast Hwy, get your game on at Sandland Adventures, and then admire the sheer force of Sweet Creek Falls.

To see more things to do, reviews, ratings, and tourist information, read Yachats trip planner .

You can drive from Cannon Beach to Yachats in 3.5 hours. Other options are to do a combination of bus, flight, and car; or take a bus. When traveling from Cannon Beach in September, plan for a bit cooler days and about the same nights in Yachats: temperatures range from 64°F by day to 50°F at night. Finish your sightseeing early on the 9th (Wed) so you can travel to Bend.

Things to do in Yachats

Outdoors Scenic Drive Nature

Side Trips

Florence, Sweet Creek Falls, Oregon Coast Hwy
Highlights from your plan
Yachats coastline ©
Yachats coastline
Sandland Adventures ©
Sandland Adventures

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: Sisters (McKenzie Pass-Santiam Pass loop & Sahalie and Koosah Falls), Redmond (Sam Johnson Park & Smith Rock State Park) and Dee Wright Observatory (in Blue River). There's still lots to do: explore the activities along Deschutes River, take in the exciting artwork at Artists Gallery Sunriver, explore the striking landscape of Deschutes National Forest, and look and learn at Oregon Observatory.

To see maps, ratings, and other tourist information, go to the Bend online trip planner .

You can do a combination of car and bus from Yachats to Bend in 4.5 hours. Other options are to drive; or do a combination of car and flight. When traveling from Yachats in September, plan for a bit warmer days and slightly colder nights in Bend: temperatures range from 73°F by day to 44°F at night. Wrap up your sightseeing on the 12th (Sat) early enough to travel to The Dalles.

Things to do in Bend

Parks Nature Outdoors

Side Trips

Sunriver, Redmond, Sisters, Dee Wright Observatory
Highlights from your plan
Smith Rock State Park ©
Smith Rock State Park
Deschutes National  Forest ©
Deschutes National Forest
McKenzie Pass-Santiam Pass loop ©
McKenzie Pass-Santiam Pass loop

3
nights
The Dalles

The Dalles ©
The Dalles is the county seat and largest city of Wasco County, Oregon, United States. Explore the numerous day-trip ideas around The Dalles: Trillium Lake (in Government Camp), Hood River (Western Antique Aeroplane & Automobile Museum & Port Marina Park) and Timberline Lodge and Ski Area (in Timberline Lodge). The adventure continues: explore the activities along Columbia River Gorge National Scenic Area, see the interesting displays at Columbia Gorge Discovery Center & Museum, and learn about all things military at Fort Dalles Museum and Anderson Homestead.

To find where to stay, more things to do, reviews, and tourist information, use the The Dalles trip planner .

You can drive from Bend to The Dalles in 3 hours. Traveling from Bend in September, expect The Dalles to be somewhat warmer, temps between 80°F and 54°F. Cap off your sightseeing on the 15th (Tue) early enough to travel back home.

Things to do in The Dalles

Nature Parks Museums

Side Trips

Hood River, Trillium Lake, Columbia River Gorge National Scenic Area, Timberline Lodge and Ski Area
Highlights from your plan

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