30 days in Oregon Itinerary

30 days in Oregon Itinerary

Created using Inspirock Oregon trip planner

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Route & dates

30 days in Oregon Itinerary

Start: Calgary
Fly:  5​h 30​min
1
Portland
— 4 nights
Drive:  2​h
2
Eugene
— 3 nights
bus:  2​h 30​min
3
Bend
— 3 nights
Drive:  2​h 45​min
4
Crater Lake National Park
— 3 nights
Drive:  2​h 15​min
5
Ashland
— 2 nights
Drive:  4​h 15​min
6
Florence
— 3 nights
Drive:  1​h 15​min
7
Newport
— 3 nights
Drive:  1​h 45​min
8
Tillamook
— 2 nights
Drive:  1​h 45​min
9
Astoria
— 3 nights
Drive:  3​h
10
Hood River
— 3 nights
Drive + Fly:  7​h
End: Calgary

4
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.
Dedicate the 2nd (Mon) to wine at some of the top wineries in the area. There's much more to do: admire the natural beauty at Portland Japanese Garden, indulge your taste buds at Food & Drink, tour the pleasant surroundings at Forest Park, and look for gifts at Powell's City of Books.

To find where to stay, maps, other places to visit, and more tourist information, go to the Portland day trip planning website .

Calgary, Canada to Portland is an approximately 5.5-hour flight. You can also drive; or take a bus. Due to the time zone difference, you'll gain 1 hour traveling from Calgary to Portland. In September, Portland is somewhat warmer than Calgary - with highs of 28°C and lows of 15°C. Wrap up your sightseeing on the 5th (Thu) to allow time to drive to Eugene.

Things to do in Portland

Tours Parks Outdoors
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

3
nights
Eugene

Eugene ©
Eugene is a city of the Pacific Northwest located in the U.S. You'll find plenty of places to visit near Eugene: Thompson's Mill State Heritage Site (in Shedd) and The Historic Carousel and Museum (in Albany). There's much more to do: explore and take pictures at Autzen Stadium, don't miss a visit to The Official Simpsons Mural, stroll through Willamette River bike trail, and look for all kinds of wild species at Cascades Raptor Center.

To find reviews, more things to do, where to stay, and other tourist information, use the Eugene trip itinerary planning site .

You can drive from Portland to Eugene in 2 hours. Alternatively, you can take a bus; or fly. Expect a bit cooler evenings in Eugene when traveling from Portland in September, with lows around 11°C. Finish your sightseeing early on the 8th (Sun) to allow enough time to take a bus to Bend.

Things to do in Eugene

Outdoors Parks Trails

Side Trips

Thompson's Mill State Heritage Site, The Historic Carousel and Museum, The Official Simpsons Mural
Highlights from your plan
Spencer Butte ©
Spencer Butte
Autzen Stadium ©
Autzen Stadium
The Historic Carousel and Museum ©
The Historic Carousel and Museum

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 Bend's surroundings by going to Dee Wright Observatory (in Blue River), Smith Rock State Park (in Redmond) and Sisters (McKenzie Pass-Santiam Pass loop & Sahalie and Koosah Falls). And it doesn't end there: explore the world behind art at High Desert Museum, take a peaceful walk through Deschutes National Forest, take an in-depth tour of Des Chutes Historical Museum, and contemplate the waterfront views at Deschutes River.

To find photos, ratings, where to stay, and more tourist information, refer to the Bend journey tool .

Traveling by bus from Eugene to Bend takes 2.5 hours. Alternatively, you can drive. Traveling from Eugene in September, you can expect nighttime temperatures to be a bit cooler in Bend, with lows of 7°C. Finish up your sightseeing early on the 11th (Wed) so you can go by car to Crater Lake National Park.

Things to do in Bend

Parks Nature Museums

Side Trips

Sisters, Dee Wright Observatory, Smith Rock State Park
Highlights from your plan
Smith Rock State Park ©
Smith Rock State Park
High Desert Museum ©
High Desert Museum
McKenzie Pass-Santiam Pass loop ©
McKenzie Pass-Santiam Pass loop

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.
Spend the 12th (Thu) exploring nature at Crater Lake National Park. There's still lots to do: take a memorable drive along Rim Dr, stroll through Cleetwood Cove Trail, take your sightseeing to a higher altitude at Watchman Peak, and trek along Garfield Peak.

To see other places to visit, reviews, more things to do, and other tourist information, you can read our Crater Lake National Park trip website .

Getting from Bend to Crater Lake National Park by car takes about 3 hours. Other options: do a combination of bus and taxi. Traveling from Bend in September, things will get somewhat warmer in Crater Lake National Park: highs are around 33°C and lows about 13°C. Cap off your sightseeing on the 14th (Sat) early enough to go by car to Ashland.

Things to do in Crater Lake National Park

Parks Outdoors Nature
Highlights from your plan
Crater Lake National Park ©
Crater Lake National Park
Rim Dr ©
Rim Dr
Cleetwood Cove Trail ©
Cleetwood Cove Trail

2
nights
Ashland

Ashland is a city in Jackson County, in the State of Oregon. Kick off your visit on the 15th (Sun): stroll through Lithia Park, look for gifts at Tudor Guild Shop, and then contemplate the waterfront views at Rogue River. On the 16th (Mon), you'll have a packed day of sightseeing: see a show at Oregon Shakespeare Festival and then relax and float downstream with a rafting and tubing tour.

To see where to stay, maps, and other tourist information, you can read our Ashland trip planner .

You can drive from Crater Lake National Park to Ashland in 2.5 hours. Another option is to take a bus. In September, plan for daily highs up to 33°C, and evening lows to 13°C. Cap off your sightseeing on the 16th (Mon) early enough to go by car to Florence.

Things to do in Ashland

Tours Outdoors Adventure

Side Trip

Rogue River
Highlights from your plan
River Rafting & Tubing
Lithia Park ©
Lithia Park
Oregon Shakespeare Festival ©
Oregon Shakespeare Festival

3
nights
Florence

Florence ©
Florence is a coastal city in Lane County, in the U.S. Explore Florence's surroundings by going to Cape Perpetua Visitor Center - Siuslaw National Forest (in Yachats) and Coos Bay (Cranberry Sweets & Shore Acres State Park). There's lots more to do: putt your heart out at Sandland Adventures, snap pictures at Siuslaw River Bridge, see the interesting displays at Given Back Bird Houses Working Museum, and enjoy the sea views from Heceta Head Lighthouse.

For where to stay, reviews, ratings, and more tourist information, go to the Florence trip itinerary planner.

You can drive from Ashland to Florence in 4.5 hours. Other options are to take a bus; or do a combination of bus and flight. Traveling from Ashland in September, you will find days in Florence are little chillier (23°C), and nights are about the same (13°C). Finish up your sightseeing early on the 19th (Thu) so you can go by car to Newport.

Things to do in Florence

Nature Parks Fun & Games

Side Trips

Coos Bay, Cape Perpetua Visitor Center - Siuslaw National Forest
Highlights from your plan
Shore Acres State Park ©
Shore Acres State Park
Heceta Head Lighthouse ©
Heceta Head Lighthouse

3
nights
Newport

Newport ©
A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
Get out of town with these interesting Newport side-trips: Yachats coastline (in Yachats) and Lincoln City Glass Center (in Lincoln City). Next up on the itinerary: look for all kinds of wild species at Yaquina Head Outstanding Natural Area, enjoy the sea views from Yaquina Head Lighthouse, take a leisurely stroll along Newport's Historic Bayfront, and tour the pleasant surroundings at Nye Beach.

To see other places to visit, traveler tips, ratings, and more tourist information, refer to the Newport travel route planning site .

You can drive from Florence to Newport in 1.5 hours. Alternatively, you can take a bus. In September, plan for daily highs up to 20°C, and evening lows to 11°C. Wrap up your sightseeing on the 22nd (Sun) to allow time to drive to Tillamook.

Things to do in Newport

Parks Outdoors Beaches

Side Trips

Otter Crest Loop, Lincoln City Glass Center, Yachats coastline
Highlights from your plan
Yachats coastline ©
Yachats coastline
Yaquina Head Outstanding Natural Area ©
Oregon Coast Aquarium ©
Oregon Coast Aquarium

2
nights
Tillamook

Tillamook ©
The city of Tillamook is the county seat of Tillamook County, Oregon, United States. Start off your visit on the 23rd (Mon): admire the majestic nature at Nehalem Bay State Park, then tour the pleasant surroundings at Manzanita Beach, and then kick back and relax at Rockaway Beach Wayside. On the 24th (Tue), you'll have a packed day of sightseeing: look for gifts at Blue Heron Cheese & Wine Company, then visit a coastal fixture at Cape Meares Lighthouse, then steep yourself in history at Tillamook Air Museum, and finally explore and take pictures at Three Capes Scenic Drive.

For other places to visit, traveler tips, more things to do, and other tourist information, read Tillamook trip builder .

You can drive from Newport to Tillamook in 2 hours. Alternatively, you can take a bus. You'll lose 1 hour traveling from Newport to Tillamook due to the time zone difference. September in Tillamook sees daily highs of 24°C and lows of 10°C at night. Finish up your sightseeing early on the 24th (Tue) so you can go by car to Astoria.

Things to do in Tillamook

Outdoors Parks Beaches

Side Trips

Manzanita Beach, Nehalem Bay State Park, Rockaway Beach Wayside, Three Capes Scenic Drive
Highlights from your plan
Rockaway Beach Wayside ©
Rockaway Beach Wayside
Nehalem Bay State Park ©
Nehalem Bay State Park
Tillamook Air Museum ©
Tillamook Air Museum

3
nights
Astoria

Astoria ©
Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
Explore the numerous day-trip ideas around Astoria: Cannon Beach (Ecola State Park, Haystack Rock, & more). There's lots more to do: explore and take pictures at Astoria Column, contemplate the waterfront views at Columbia River Maritime Museum, examine the collection at Flavel House Museum, and immerse yourself in nature at Fort Stevens State Park.

To find where to stay, traveler tips, more things to do, and other tourist information, refer to the Astoria trip planner .

You can drive from Tillamook to Astoria in 2 hours. Alternatively, you can take a bus. The time zone difference when traveling from Tillamook to Astoria is minus 1 hour. September in Astoria sees daily highs of 24°C and lows of 13°C at night. Cap off your sightseeing on the 27th (Fri) early enough to go by car to Hood River.

Things to do in Astoria

Parks Nature Outdoors

Side Trips

Cannon Beach, Seaside Inverted Experience
Highlights from your plan
Haystack Rock ©
Haystack Rock
Ecola State Park ©
Ecola State Park
Cannon Beach ©
Cannon Beach

3
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. Explore Hood River's surroundings by going to Multnomah Falls (in Troutdale), Bonneville Lock & Dam (in Cascade Locks) and Multnomah Falls (in Bridal Veil). And it doesn't end there: look for all kinds of wild species at Columbia River Gorge National Scenic Area, learn about winemaking at Marchesi Vineyards, see the interesting displays at Western Antique Aeroplane & Automobile Museum, and trek along Historic Columbia River Highway State Trail.

To find reviews, maps, other places to visit, and more tourist information, go to the Hood River itinerary builder site .

Traveling by car from Astoria to Hood River takes 3 hours. Alternatively, you can take a bus; or do a combination of bus and train. Expect a daytime high around 25°C in September, and nighttime lows around 16°C. Cap off your sightseeing on the 30th (Mon) early enough to travel back home.

Things to do in Hood River

Parks Nature Wildlife

Side Trips

Historic Columbia River Highway State Trail, Columbia Gorge Discovery Center & Museum, Columbia River Gorge National Scenic Area, Multnomah Falls, Bonneville Lock & Dam
Highlights from your plan
Multnomah Falls ©
Multnomah Falls

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