31 days in Oregon Itinerary

31 days in Oregon Itinerary

Created using Inspirock Oregon trip planner

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Route & dates

31 days in Oregon Itinerary

Start: New York City
bus + Fly:  11​h 30​min
1
Bend
— 4 nights
Drive:  3​h 30​min
2
Klamath Falls
— 3 nights
Drive:  1​h 30​min
3
Ashland
— 3 nights
Drive:  4​h 15​min
4
Florence
— 3 nights
Drive:  1​h 15​min
5
Newport
— 3 nights
Drive:  3​h 30​min
6
Astoria
— 4 nights
Drive:  3​h
7
Hood River
— 4 nights
bus:  1​h 15​min
8
Portland
— 6 nights
Fly + foot:  9​h
End: New York City

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.
Get out of town with these interesting Bend side-trips: Dee Wright Observatory (in Blue River), Artists Gallery Sunriver (in Sunriver) and Sisters (McKenzie Pass-Santiam Pass loop & Sahalie and Koosah Falls). There's lots more to do: admire the majestic nature at Smith Rock State Park, delve into the lush surroundings at Deschutes National Forest, hike along Pilot Butte State Scenic Viewpoint, and explore the activities along Deschutes River.

To plan Bend vacation without wasting time, ask Inspirock to design an itinerary.

New York City to Bend is an approximately 11.5-hour combination of bus and flight. You can also fly; or drive. The time zone difference when traveling from New York City to Bend is minus 3 hours. Traveling from New York City in August, plan for a bit cooler nights in Bend, with lows around 52°F. Finish your sightseeing early on the 5th (Mon) to allow enough time to travel to Klamath Falls.

Things to do in Bend

Parks Nature Museums

Side Trips

Sunriver, Sisters, Smith Rock State Park, Dee Wright Observatory
Highlights from your plan
Smith Rock State Park ©
Smith Rock State Park
High Desert Museum ©
High Desert Museum
Deschutes River ©
Deschutes River

3
nights
Klamath Falls

Klamath Falls ©
Klamath Falls is a city in and the county seat of Klamath County, Oregon, United States. You'll find plenty of places to visit near Klamath Falls: Crater Lake National Park (Pinnacles Trail, Crater Lake National Park, & more). There's more to do: explore the activities along Wood River Wetland.

Plan my Klamath Falls trip by asking Inpirock to come up with tips and suggestions.

Traveling by car from Bend to Klamath Falls takes 2.5 hours. In August in Klamath Falls, expect temperatures between 86°F during the day and 48°F at night. Finish your sightseeing early on the 8th (Thu) to allow enough time to drive to Ashland.

Things to do in Klamath Falls

Parks Nature Outdoors

Side Trip

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

3
nights
Ashland

Ashland is a city in Jackson County, in the State of Oregon. Change things up with these side-trips from Ashland: Grants Pass (Wildlife Images - Rehabilitation & Education Center, The Glass Forge, & more), Rogue River (in Medford) and Oregon Caves National Monument and Preserve (in Cave Junction). And it doesn't end there: let the river carry you with a rafting and tubing tour, catch a live performance at Oregon Shakespeare Festival, get lost in a book at Jackson County Genealogy Library, and do a tasting at LongSword Vineyard.

For more things to do, other places to visit, photos, and other tourist information, read Ashland travel route planner .

You can drive from Klamath Falls to Ashland in 1.5 hours. Traveling from Klamath Falls in August, expect Ashland to be a bit warmer, temps between 93°F and 60°F. Finish your sightseeing early on the 11th (Sun) so you can drive to Florence.

Things to do in Ashland

Parks Nature Tours

Side Trips

Grants Pass, Medford, Oregon Caves National Monument and Preserve, LongSword Vineyard
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. Change things up with these side-trips from Florence: Yachats (Cape Perpetua Visitor Center - Siuslaw National Forest & Devil's Churn). The adventure continues: putt your heart out at Sandland Adventures, visit a coastal fixture at Heceta Head Lighthouse, explore the fascinating underground world of Sea Lion Caves, and get in on the excitement at Sand Master Park.

For where to stay, traveler tips, maps, and other tourist information, read our Florence road trip tool .

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 August, you will find days in Florence are colder (68°F), and nights are little chillier (54°F). Wrap up your sightseeing on the 14th (Wed) early enough to drive to Newport.

Things to do in Florence

Nature Parks Outdoors

Side Trips

Yachats, Oregon Coast Hwy
Highlights from your plan
Sandland Adventures ©
Sandland Adventures
Sand Master Park ©
Sand Master Park

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: Lincoln City Glass Center (in Lincoln City), Yachats coastline (in Yachats) and Proposal Rock (in Neskowin). There's still lots to do: look for all kinds of wild species at Yaquina Head Outstanding Natural Area, explore the galleries of Hatfield Marine Science Center, take in the waterfront at Newport's Historic Bayfront, and examine the collection at The Historic Carousel and Museum.

To find reviews, other places to visit, traveler tips, and tourist information, go to the Newport planner .

Drive from Florence to Newport in 1.5 hours. Alternatively, you can take a bus. August in Newport sees daily highs of 64°F and lows of 51°F at night. Wrap up your sightseeing on the 17th (Sat) to allow time to drive to Astoria.

Things to do in Newport

Parks Museums Nature

Side Trips

Yachats coastline, Lincoln City Glass Center, The Historic Carousel and Museum, Proposal Rock
Highlights from your plan
Yachats coastline ©
Yachats coastline
Oregon Coast Aquarium ©
Oregon Coast Aquarium
Newport's Historic Bayfront ©
Newport's Historic Bayfront

4
nights
Astoria

Astoria ©
Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
Change things up with these side-trips from Astoria: Cannon Beach (Haystack Rock, Cannon Beach, & more) and Seaside (Arcadia Beach State Recreation Area & Seaside Aquarium). The adventure continues: appreciate the history behind Astoria Column, admire the majestic nature at Fort Stevens State Park, see the interesting displays at Columbia River Maritime Museum, and admire all the interesting features of Fort Clatsop National Memorial.

For ratings, where to stay, reviews, and more tourist information, you can read our Astoria tour itinerary planner.

Getting from Newport to Astoria by car takes about 3.5 hours. Other options: take a bus. When traveling from Newport in August, plan for a bit warmer days and about the same nights in Astoria: temperatures range from 71°F by day to 55°F at night. Finish your sightseeing early on the 21st (Wed) to allow enough time to drive to Hood River.

Things to do in Astoria

Parks Nature Outdoors

Side Trips

Cannon Beach, Seaside
Highlights from your plan
Ecola State Park ©
Ecola State Park
Cannon Beach ©
Cannon Beach
Oswald West State Park ©
Oswald West State Park

4
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. Change things up with these side-trips from Hood River: The Dalles Murals (in The Dalles), Bonneville Lock & Dam (in Cascade Locks) and Timberline Lodge and Ski Area (in Timberline Lodge). There's still lots to do: contemplate the waterfront views at Columbia River Gorge National Scenic Area, admire the sheer force of Starvation Creek State Park, gain insight at Sturgeon Viewing Pond and Interpretive Center, and see the interesting displays at Columbia Gorge Discovery Center & Museum.

To see photos, maps, and other tourist information, go to the Hood River trip maker site .

You can drive from Astoria to Hood River in 3 hours. Other options are to take a bus; or do a combination of bus and train. Traveling from Astoria in August, you will find days in Hood River are somewhat warmer (81°F), and nights are about the same (60°F). Wrap up your sightseeing on the 25th (Sun) early enough to take a bus to Portland.

Things to do in Hood River

Parks Nature Outdoors

Side Trips

Cascade Locks, The Dalles, Historic Columbia River Highway State Trail, Timberline Lodge and Ski Area, Mt. Hood National Forest
Highlights from your plan

6
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.
Explore Portland's surroundings by going to Multnomah Falls (in Bridal Veil) and Evergreen Aviation & Space Museum (in McMinnville). The adventure continues: take in nature's colorful creations at Portland Japanese Garden, contemplate the long history of Pittock Mansion, head outdoors with Portland Timbers, and test your problem-solving skills at popular escape rooms.

To find ratings and other tourist information, go to the Portland trip itinerary builder app .

You can take a bus from Hood River to Portland in 1.5 hours. Other options are to drive; or take a train. Expect a daytime high around 85°F in August, and nighttime lows around 60°F. You'll have a few hours on the 31st (Sat) to wrap things up before traveling home.

Things to do in Portland

Parks Tours Museums

Side Trips

Multnomah Falls, Evergreen Aviation & Space Museum
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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