21 days in Oregon Itinerary

21 days in Oregon Itinerary

Created using Inspirock Oregon trip planner

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Route & dates

21 days in Oregon Itinerary

Start: Portland
Drive:  50​h
1
Hood River
— 2 nights
Drive:  3​h
2
Cannon Beach
— 2 nights
Drive:  3​h 15​min
3
Yachats
— 2 nights
Drive:  2​h 30​min
4
Bandon
— 2 nights
Drive:  2​h 45​min
5
Prospect
— 2 nights
Drive:  3​h
6
Bend
— 4 nights
Drive:  3​h 30​min
7
Portland
— 3 nights
+2
Fly + foot + bus:  10​h 15​min
End: Portland

2
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. Start off your visit on the 17th (Tue): get outside with Big Winds and then take in the exciting artwork at Art on Oak. Get ready for a full day of sightseeing on the next day: identify plant and animal life at Starvation Creek State Park and then tour the pleasant surroundings at Mount Hood.

To find more things to do, where to stay, ratings, and tourist information, go to the Hood River trip itinerary builder tool .

Portland to Hood River is an approximately 12.5-hour combination of bus and flight. You can also do a combination of flight and bus; or drive. The time zone changes from Eastern Standard Time to Pacific Standard Time, which is usually a -3 hour difference. In September, daytime highs in Hood River are 71°F, while nighttime lows are 57°F. Finish up your sightseeing early on the 19th (Thu) so you can go by car to Cannon Beach.

Things to do in Hood River

Parks Outdoors Nature

Side Trips

Cascade Locks, Beacon Rock, Rowena Crest Viewpoint
Highlights from your plan
Mount Hood ©
Mount Hood
Beacon Rock ©
Beacon Rock
Starvation Creek State Park ©
Starvation Creek State Park

2
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. Start off your visit on the 20th (Fri): view the masterpieces at Icefire Glassworks, immerse yourself in nature at Hug Point State Park, then take in the dramatic natural features at Haystack Rock, and finally take in the exciting artwork at Bronze Coast Gallery. On the next day, look for gifts at Bruce's Candy Kitchen, admire the majestic nature at Oswald West State Park, and then hike along Astoria Oregon Riverwalk.

To see photos, where to stay, more things to do, and more tourist information, use the Cannon Beach trip maker tool .

Traveling by car from Hood River to Cannon Beach takes 3 hours. Alternatively, you can take a bus; or do a combination of train and bus. Expect little chillier evenings in Cannon Beach when traveling from Hood River in September, with lows around 52°F. Wrap up your sightseeing on the 21st (Sat) to allow time to drive to Yachats.

Things to do in Cannon Beach

Parks Nature Outdoors

Side Trip

Astoria Oregon Riverwalk
Highlights from your plan
Hug Point State Park ©
Hug Point State Park
Oswald West State Park ©
Oswald West State Park
Astoria Oregon Riverwalk ©
Astoria Oregon Riverwalk

2
nights
Yachats

Yachats ©
Yachats is a small coastal city in Lincoln County, Oregon, United States. On the 22nd (Sun), admire the sheer force of Sweet Creek Falls, hike along Hobbit Trail, then take in the dramatic natural features at Thor's Well, and finally admire the majestic nature at Yachats State Park. On the 23rd (Mon), you'll have a packed day of sightseeing: take a memorable drive along Oregon Coast Hwy, then take a memorable drive along Cape Perpetua Visitor Center - Siuslaw National Forest, and then admire the majestic nature at Muriel O. Ponsler Memorial State Scenic Viewpoint.

To see where to stay, more things to do, traveler tips, and tourist information, read Yachats itinerary planning tool .

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. Expect slightly colder weather when traveling from Cannon Beach in September: highs in Yachats hover around 64°F, while lows dip to 50°F. Finish up your sightseeing early on the 23rd (Mon) so you can go by car to Bandon.

Things to do in Yachats

Parks Nature Outdoors

Side Trips

Florence, Oregon Coast Hwy, Sweet Creek Falls
Highlights from your plan

2
nights
Bandon

Bandon ©
Bandon is a city in Coos County, Oregon, United States, on the south side of the mouth of the Coquille River. On the 24th (Tue), get engrossed in the history at Bandon Historical Society Museum, then view the masterpieces at Second Street Gallery, then stroll through Coquille Point, and finally explore the striking landscape at Face Rock State Scenic Viewpoint. Here are some ideas for day two: trek along South Slough National Estuarine Research Reserve and then admire the majestic nature at Bullards Beach State Park.

For more things to do, maps, reviews, and tourist information, go to the Bandon vacation site .

Getting from Yachats to Bandon by car takes about 2.5 hours. Other options: do a combination of taxi and bus. In September, daytime highs in Bandon are 68°F, while nighttime lows are 52°F. Cap off your sightseeing on the 25th (Wed) early enough to travel to Prospect.

Things to do in Bandon

Parks Wildlife Nature

Side Trip

South Slough National Estuarine Research Reserve
Highlights from your plan
Face Rock State Scenic Viewpoint ©
Face Rock State Scenic Viewpoint
Bullards Beach State Park ©
Bullards Beach State Park

2
nights
Prospect

Prospect ©
Prospect is an unincorporated community in Jackson County, in the U.S. Start off your visit on the 26th (Thu): explore the striking landscape of Crater Lake National Park. On the next day, take in the dramatic scenery at Plaikni Falls, take in the awesome beauty at Watchman Peak, then take in the dramatic scenery at National Creek Falls, and finally admire the sheer force of Mill Creek Falls.

To find where to stay, maps, photos, and more tourist information, you can read our Prospect holiday planner.

Drive from Bandon to Prospect in 3.5 hours. Traveling from Bandon in September, you will find days in Prospect are somewhat warmer (83°F), and nights are about the same (53°F). Wrap up your sightseeing on the 27th (Fri) to allow time to travel to Bend.

Things to do in Prospect

Nature Parks Trails

Side Trip

Crater Lake National Park
Highlights from your plan
Crater Lake National Park ©
Crater Lake National Park
Watchman Peak ©
Watchman Peak
Plaikni Falls ©
Plaikni Falls

4
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.
Step off the beaten path and head to River Rafting & Tubing and Deschutes River Trail. Get outdoors at Newberry National Volcanic Monument and High Desert Museum. Change things up with these side-trips from Bend: McKenzie River National Recreation Trail (in Eugene) and Willamette National Forest (in Mill City). The adventure continues: walk around Shevlin Park, take in the awesome beauty at South Sister, contemplate the waterfront views at North and South Twin Lakes, and indulge your thirst for a good beer at Atlas Cider Co.

For reviews and more tourist information, read Bend online travel planner .

You can drive from Prospect to Bend in 2.5 hours. In September, Bend is a bit cooler than Prospect - with highs of 73°F and lows of 44°F. Wrap up your sightseeing on the 1st (Tue) to allow time to drive to Portland.

Things to do in Bend

Parks Nature Outdoors

Side Trips

McKenzie River National Recreation Trail, Willamette National Forest
Highlights from your plan
Newberry National Volcanic Monument ©
Willamette National Forest ©
Willamette National Forest
High Desert Museum ©
High Desert Museum

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.
Kick off your visit on the 2nd (Wed): stroll through Magness Memorial Tree Farm and then appreciate the views at Willamette Valley. Get ready for a full day of sightseeing on the next day: delve into the lush surroundings at Camassia Natural Area, immerse yourself in nature at Milo McIver State Park, then do a tasting at Natalies Estate Winery, and finally identify plant and animal life at Tualatin River National Wildlife Refuge.

For reviews, where to stay, ratings, and other tourist information, refer to the Portland online trip itinerary maker .

Getting from Bend to Portland by car takes about 3.5 hours. Other options: fly; or take a bus. Traveling from Bend in October, plan for somewhat warmer nights in Portland, with lows around 49°F. Wrap up your sightseeing by early afternoon on the 4th (Fri) to allow time for travel back home.

Things to do in Portland

Parks Nature Outdoors

Side Trips

Sherwood, Natalies Estate Winery, Camassia Natural Area, Museum of the Oregon Territory
Highlights from your plan
Willamette Valley ©
Willamette Valley
Camassia Natural Area ©
Camassia Natural Area

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