45 days in Oregon Itinerary

45 days in Oregon Itinerary

Created using Inspirock Oregon trip builder

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Route & dates

45 days in Oregon Itinerary

Start: Portland
Drive:  1​h 30​min
1
Cannon Beach
— 4 nights
Drive:  2​h 45​min
2
Newport
— 4 nights
Drive:  1​h 15​min
3
Florence
— 4 nights
Drive:  2​h
4
Roseburg
— 5 nights
Drive:  2​h
5
Ashland
— 4 nights
Drive:  1​h 30​min
6
Klamath Falls
— 5 nights
Drive:  2​h 30​min
7
Bend
— 5 nights
Drive:  3​h 15​min
8
Hood River
— 5 nights
bus:  1​h 15​min
9
Portland
— 8 nights
End: Portland

4
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: Rockaway Beach Wayside (in Rockaway Beach) and Astoria (Fort Stevens State Park, Astoria Column, & more). And it doesn't end there: explore the striking landscape at Haystack Rock, admire nature's wide array of creatures at Seaside Aquarium, don't miss a visit to Seaside Beach Lewis and Clark Monument, and enjoy the sand and surf at Manzanita Beach.

To find photos, reviews, traveler tips, and tourist information, read Cannon Beach route planning website .

Portland to Cannon Beach is an approximately 1.5-hour car ride. You can also take a bus. While traveling from Portland, expect little chillier days and about the same nights in Cannon Beach, ranging from highs of 69°F to lows of 52°F. Finish your sightseeing early on the 5th (Thu) so you can drive to Newport.

Things to do in Cannon Beach

Parks Nature Beaches

Side Trips

Astoria, Seaside, Manzanita Beach, Nehalem Bay State Park, Rockaway Beach Wayside
Highlights from your plan
Haystack Rock ©
Haystack Rock
Ecola State Park ©
Ecola State Park
Cannon Beach ©
Cannon Beach

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.
You'll find plenty of places to visit near Newport: Lincoln City Glass Center (in Lincoln City), Yachats coastline (in Yachats) and Cape Kiwanda State Natural Area (in Pacific City). The adventure continues: identify plant and animal life at Yaquina Head Outstanding Natural Area, see majestic marine mammals with a dolphin and whale watching tour, snap pictures at Yaquina Bay Bridge, and observe the fascinating underwater world at Oregon Coast Aquarium.

To find ratings, where to stay, photos, and more tourist information, use the Newport journey planner.

You can drive from Cannon Beach to Newport in 3 hours. Another option is to take a bus. While traveling from Cannon Beach, expect a bit cooler days and about the same nights in Newport, ranging from highs of 64°F to lows of 50°F. Cap off your sightseeing on the 9th (Mon) early enough to go by car to Florence.

Things to do in Newport

Outdoors Parks Beaches

Side Trips

Depoe Bay, Yachats coastline, Lincoln City Glass Center, Cape Kiwanda State Natural Area
Highlights from your plan
Yachats coastline ©
Yachats coastline
Yaquina Head Outstanding Natural Area ©
Oregon Coast Aquarium ©
Oregon Coast Aquarium

4
nights
Florence

Florence ©
Florence is a coastal city in Lane County, in the U.S. Get out of town with these interesting Florence side-trips: Coos Bay (Shore Acres State Park & Cape Arago State Park) and Yachats (Cape Perpetua Visitor Center - Siuslaw National Forest & Devil's Churn). There's still lots to do: putt your heart out at Sandland Adventures, enjoy some diversion at Sand Master Park - Sandboarding, explore the fascinating underground world of Sea Lion Caves, and enjoy the sea views from Heceta Head Lighthouse.

Ask Inspirock to suggest an itinerary and make planning a trip to Florence fast, fun, and easy.

Traveling by car from Newport to Florence takes 1.5 hours. Alternatively, you can take a bus. In September, plan for daily highs up to 68°F, and evening lows to 52°F. Cap off your sightseeing on the 13th (Fri) early enough to go by car to Roseburg.

Things to do in Florence

Parks Nature Outdoors

Side Trips

Yachats, Coos Bay, Mindpower Gallery, Oregon Coast Hwy, Tsunami Gallery
Highlights from your plan
Shore Acres State Park ©
Shore Acres State Park
Cape Arago State Park ©
Cape Arago State Park

5
nights
Roseburg

Roseburg ©
Roseburg is a city in the U.S. You'll find plenty of places to visit near Roseburg: Spirit Falls (in Cottage Grove), Butterfly Pavilion & Gardens at ECEC (in Elkton) and Bandon (Face Rock Creamery, Face Rock State Scenic Viewpoint, & more). The adventure continues: admire the sheer force of Fall Creek Falls, contemplate the waterfront views at Colliding Rivers Park, identify plant and animal life at Wildlife Safari, and take in nature's colorful creations at Discovery Garden.

To see ratings, more things to do, other places to visit, and tourist information, go to the Roseburg day trip app .

Drive from Florence to Roseburg in 2 hours. When traveling from Florence in September, plan for a bit warmer days and about the same nights in Roseburg: temperatures range from 80°F by day to 54°F at night. Wrap up your sightseeing on the 18th (Wed) early enough to travel to Ashland.

Things to do in Roseburg

Parks Nature Wildlife

Side Trips

Bandon, Crater Lake National Park, Glide, Wildlife Safari, Rochester Covered Bridge
Highlights from your plan
Face Rock State Scenic Viewpoint ©
Face Rock State Scenic Viewpoint
Bandon Dunes Golf Resort ©
Bandon Dunes Golf Resort
Wildlife Safari ©
Wildlife Safari

4
nights
Ashland

Ashland is a city in Jackson County, in the State of Oregon. Explore the numerous day-trip ideas around Ashland: Rogue River (in Medford), Oregon Caves National Monument and Preserve (in Cave Junction) and Rolling Hills Alpacas (in Central Point). Next up on the itinerary: get a new perspective on things with Boat Tours & Water Sports, identify plant and animal life at Wildlife Images - Rehabilitation & Education Center, walk around Lithia Park, and admire all the interesting features of Rogue-Umpqua Scenic Byway.

To see ratings, other places to visit, photos, and more tourist information, you can read our Ashland vacation planner .

Drive from Roseburg to Ashland in 2 hours. In September in Ashland, expect temperatures between 83°F during the day and 53°F at night. Finish up your sightseeing early on the 22nd (Sun) so you can go by car to Klamath Falls.

Things to do in Ashland

Parks Outdoors Nature

Side Trips

Grants Pass, Jacksonville Cemetery, Oregon Caves National Monument and Preserve, Rogue River, Rogue-Umpqua Scenic Byway
Highlights from your plan
River Rafting & Tubing
Lithia Park ©
Lithia Park
Oregon Shakespeare Festival ©
Oregon Shakespeare Festival

5
nights
Klamath Falls

Klamath Falls ©
Klamath Falls is a city in and the county seat of Klamath County, Oregon, United States. Change things up with these side-trips from Klamath Falls: Collier Memorial State Park (in Chiloquin) and Crater Lake National Park (Pinnacles Trail, Crater Lake National Park, & more). There's more to do: identify plant and animal life at Badger Run Wildlife Rehab.

To see more things to do, reviews, photos, and more tourist information, read Klamath Falls driving holiday planner .

Getting from Ashland to Klamath Falls by car takes about 1.5 hours. Traveling from Ashland in September, expect Klamath Falls to be little chillier, temps between 76°F and 40°F. Finish up your sightseeing early on the 27th (Fri) so you can travel to Bend.

Things to do in Klamath Falls

Parks Outdoors Nature

Side Trips

Crater Lake National Park, Collier Memorial State Park
Highlights from your plan
Crater Lake National Park ©
Crater Lake National Park
Rim Dr ©
Rim Dr
Garfield Peak ©
Garfield Peak

5
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 Dee Wright Observatory (in Blue River). The adventure continues: get engrossed in the history at High Desert Museum, walk around Drake Park, contemplate the waterfront views at Deschutes River, and look and learn at Oregon Observatory.

To see ratings, reviews, other places to visit, and other tourist information, read Bend trip itinerary planning website .

You can drive from Klamath Falls to Bend in 2.5 hours. Expect a daytime high around 73°F in September, and nighttime lows around 44°F. Wrap up your sightseeing on the 2nd (Wed) to allow time to drive to Hood River.

Things to do in Bend

Parks Nature Outdoors

Side Trips

Sisters, Smith Rock State Park, Oregon Observatory, Dee Wright Observatory
Highlights from your plan
Smith Rock State Park ©
Smith Rock State Park
High Desert Museum ©
High Desert Museum
River Rafting & Tubing

5
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. Venture out of the city with trips to Timberline Lodge and Ski Area (in Timberline Lodge), The Dalles Murals (in The Dalles) and Trillium Lake (in Government Camp). There's still lots to do: contemplate the waterfront views at Columbia River Gorge National Scenic Area, see the interesting displays at Columbia Gorge Discovery Center & Museum, take in the pleasant sights at Rowena Crest Viewpoint, and contemplate the geological forces at Mount Hood.

To see photos, other places to visit, reviews, and more tourist information, read our Hood River trip planner .

Getting from Bend to Hood River by car takes about 3.5 hours. Other options: do a combination of flight and bus; or take a bus. Traveling from Bend in October, plan for a bit warmer nights in Hood River, with lows around 45°F. Wrap up your sightseeing on the 7th (Mon) to allow time to take a bus to Portland.

Things to do in Hood River

Parks Nature Outdoors

Side Trips

Cascade Locks, Mosier, Oregon, The Dalles, Mt. Hood National Forest
Highlights from your plan

8
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.
Get out of town with these interesting Portland side-trips: Multnomah Falls (in Troutdale), Dundee (Bella Vida Vineyard & Sokol Blosser Winery) and Multnomah Falls (in Bridal Veil). And it doesn't end there: take in nature's colorful creations at Portland Japanese Garden, indulge your senses at some of the top wineries in the area, look for gifts at Powell's City of Books, and test your team's savvy at popular escape rooms.

To see more things to do, where to stay, other places to visit, and tourist information, use the Portland itinerary planner.

Traveling by bus from Hood River to Portland takes 1.5 hours. Alternatively, you can drive; or take a train. In October, daytime highs in Portland are 66°F, while nighttime lows are 49°F. Finish up your sightseeing early on the 15th (Tue) so you can travel back home.

Things to do in Portland

Parks Tours Museums

Side Trips

Dundee, Multnomah Falls, Vietnam Era Veterans Memorial, Milwaukie Museum, Columbia River Highway
Highlights from your plan
Portland Japanese Garden ©
Portland Japanese Garden
International Rose Test Garden ©
International Rose Test Garden
Powell's City of Books ©
Powell's City of Books

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