56 days in Oregon Itinerary

56 days in Oregon Itinerary

Created using Inspirock Oregon trip itinerary planner

This plan was created by another user. Make it your plan

Route & dates

56 days in Oregon Itinerary

Start: New York City
Foot + Fly:  8​h 45​min
1
Portland
— 7 nights
Bus:  1​h 15​min
2
Hood River
— 7 nights
Drive:  3​h
3
Astoria
— 6 nights
Drive:  1​h 45​min
4
Tillamook
— 3 nights
Drive:  1​h 45​min
5
Newport
— 5 nights
Drive:  3​h
6
Bandon
— 5 nights
Drive:  2​h
7
Florence
— 5 nights
Bus:  1​h 15​min
8
Eugene
— 7 nights
Bus:  2​h 30​min
9
Bend
— 7 nights
Drive:  4​h 45​min
10
Baker City
— 2 nights
+2
Drive + Fly + Drive:  13​h
End: New York City

7
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 Art Museum and Evergreen Aviation & Space Museum will appeal to museum buffs. Do some cultural sightseeing at Oregon Garden and Pearl District. Explore the numerous day-trip ideas around Portland: Silver Falls State Park (in Sublimity), Corbett (Vista House & Bridal Veil Falls State Park) and Multnomah Falls (in Bridal Veil). There's much more to do: admire the verdant scenery at Willamette Valley, hike along Forest Park, tour the pleasant surroundings at Columbia River Highway, and learn about winemaking at Soter Vineyards.

To see ratings, photos, other places to visit, and more tourist information, you can read our Portland route builder app .

New York City to Portland is an approximately 9-hour combination of bus and flight. You can also do a combination of train and flight; or drive. Traveling from New York City to Portland, you'll gain 3 hours due to the time zone difference. Traveling from New York City in March, expect Portland to be somewhat warmer, temps between 58°F and 41°F. Finish up your sightseeing early on the 13th (Tue) so you can go by car to Hood River.

Things to do in Portland

Parks Nature Wineries

Side Trips

Dayton, Corbett, Silverton, Multnomah Falls, Columbia River Highway
Highlights from your plan
Willamette Valley ©
Willamette Valley
Columbia River Highway ©
Columbia River Highway
Willamette Valley Vineyards ©
Willamette Valley Vineyards

7
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. Museum-lovers will appreciate Columbia Gorge Discovery Center & Museum and Western Antique Aeroplane & Automobile Museum. Get a sense of the local culture at Timberline Lodge and Ski Area and Naked Winery Hood River Tasting Room. Venture out of the city with trips to Oneonta Gorge (in Cascade Locks), Imperial River Company (in Maupin) and Trillium Lake (in Government Camp). Next up on the itinerary: contemplate the geological forces at Mount Hood, do a tasting at Sunshine Mill Winery, hike along Historic Columbia River Highway State Trail, and experience rural life at Hood River Lavender.

To find more things to do, maps, ratings, and more tourist information, go to the Hood River tour website .

Traveling by car from Portland to Hood River takes 1.5 hours. Alternatively, you can take a bus; or take a train. Traveling from Portland in March, you will find days in Hood River are slightly colder (49°F), and nights are about the same (39°F). Finish your sightseeing early on the 20th (Tue) to allow enough time to drive to Astoria.

Things to do in Hood River

Outdoors Parks Nature

Side Trips

The Dalles, Cascade Locks, Trillium Lake, Imperial River Company, Columbia River Gorge National Scenic Area
Highlights from your plan
Mount Hood ©
Mount Hood
Timberline Lodge and Ski Area ©
Timberline Lodge and Ski Area

6
nights
Astoria

Astoria ©
Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
Get some cultural insight at Fort Clatsop National Memorial and The Lewis And Clark National And State Historical Parks. Visiting Haystack Rock and Astoria Oregon Riverwalk will get you outdoors. You'll find plenty of places to visit near Astoria: Cannon Beach (Hug Point State Park, Oswald West State Park, & more) and Seaside (Beach Books & Camp 18 Logging Museum & Restaurant). There's lots more to do: see the interesting displays at Flavel House Museum, explore the activities along Columbia River Maritime Museum, look for all kinds of wild species at Astoria Column, and snap pictures at Astoria-Megler Bridge.

To find where to stay, reviews, photos, and tourist information, use the Astoria attractions planner.

You can drive from Hood River to Astoria in 3 hours. Alternatively, you can take a bus; or do a combination of train and bus. In March in Astoria, expect temperatures between 53°F during the day and 40°F at night. Wrap up your sightseeing on the 26th (Mon) early enough to drive to Tillamook.

Things to do in Astoria

Parks Nature Historic Sites

Side Trips

Cannon Beach, Seaside
Highlights from your plan
Fort Clatsop National Memorial ©
Fort Clatsop National Memorial
Flavel House Museum ©
Flavel House Museum

3
nights
Tillamook

Tillamook ©
The city of Tillamook is the county seat of Tillamook County, Oregon, United States. Museum-lovers will appreciate Tillamook Air Museum and Garibaldi Museum. Satisfy your inner culture vulture at Cape Meares Lighthouse and Nehalem Bay Winery. Venture out of the city with trips to Cape Kiwanda State Natural Area (in Pacific City) and Manzanita (Spas & Wellness & Manzanita Beach). There's still lots to do: admire the majestic nature at Cape Lookout State Park and look for gifts at Blue Heron Cheese & Wine Company.

To see traveler tips, reviews, photos, and tourist information, you can read our Tillamook road trip app .

Traveling by car from Astoria to Tillamook takes 2 hours. Alternatively, you can take a bus. Due to the time zone difference, you'll lose 1 hour traveling from Astoria to Tillamook. In March, daytime highs in Tillamook are 54°F, while nighttime lows are 40°F. Finish up your sightseeing early on the 29th (Thu) so you can go by car to Newport.

Things to do in Tillamook

Parks Outdoors Beaches

Side Trips

Nehalem Bay Winery, Garibaldi Museum, Manzanita Beach, Cape Kiwanda State Natural Area
Highlights from your plan
Cape Meares Lighthouse ©
Cape Meares Lighthouse
Cape Kiwanda State Natural Area ©
Cape Kiwanda State Natural Area
Cape Lookout State Park ©
Cape Lookout State Park

5
nights
Newport

Newport ©
A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
Step out of the city life by going to Nye Beach and Devil's Churn. Do some cultural sightseeing at Hatfield Marine Science Center and North Lincoln County Historical Museum. Venture out of the city with trips to Yachats coastline (in Yachats) and Lincoln City (Jennifer Sears Glass Art Studio, Alderhouse Glass Blowers, & more). The adventure continues: admire the majestic nature at Devils Punchbowl State Natural Area, take a memorable drive along Otter Crest Loop, look for all kinds of wild species at Yaquina Bay State Recreation Area, and enjoy the sand and surf at Agate Beach State Park.

To see reviews, traveler tips, other places to visit, and more tourist information, read our Newport road trip tool .

Traveling by car from Tillamook to Newport takes 2 hours. Alternatively, you can take a bus. Traveling from Tillamook to Newport, you'll gain 1 hour due to the time zone difference. Expect a daytime high around 52°F in March, and nighttime lows around 41°F. Finish up your sightseeing early on the 3rd (Tue) so you can go by car to Bandon.

Things to do in Newport

Parks Nature Outdoors

Side Trips

Lincoln City, Depoe Bay, Yachats
Highlights from your plan
Fogarty Creek State Recreation Area ©
Nye Beach ©
Nye Beach
Devil's Churn ©
Devil's Churn

5
nights
Bandon

Bandon ©
Bandon is a city in Coos County, Oregon, United States, on the south side of the mouth of the Coquille River. Do some cultural sightseeing at Cape Blanco Lighthouse and Hughes Historic House. You'll discover tucked-away gems like Face Rock State Scenic Viewpoint and Wildlife Safari. Explore the numerous day-trip ideas around Bandon: Wildlife Images - Rehabilitation & Education Center (in Grants Pass), Shore Acres State Park (in Coos Bay) and Cape Blanco State Park (in Port Orford). Next up on the itinerary: identify plant and animal life at West Coast Game Park Safari, enjoy the sea views from Coquille River Lighthouse, and stop by Cranberry Sweets.

To find maps, reviews, and more tourist information, read our Bandon online travel planner .

Traveling by car from Newport to Bandon takes 3 hours. Alternatively, you can do a combination of bus and taxi; or take a bus. Expect a daytime high around 56°F in April, and nighttime lows around 43°F. Finish your sightseeing early on the 8th (Sun) so you can drive to Florence.

Things to do in Bandon

Parks Wildlife Nature

Side Trips

Port Orford, Wildlife Images - Rehabilitation & Education Center, Shore Acres State Park, Wildlife Safari
Highlights from your plan
Face Rock State Scenic Viewpoint ©
Wildlife Safari ©
Wildlife Safari
Cape Blanco Lighthouse ©
Cape Blanco Lighthouse

5
nights
Florence

Florence ©
Florence is a coastal city in Lane County, in the U.S. Step out of the city life by going to Oregon Dunes National Recreation Area and Hobbit Trail. You'll explore the less-touristy side of things at Dean Creek Elk Viewing Area and John Dellenback Dunes Trailhead. Venture out of the city with trips to Elkton (Brandborg Vineyard and Winery & River's Edge Winery), Umpqua River Lighthouse (in Winchester Bay) and Henry Estate Winery (in Umpqua). And it doesn't end there: putt your heart out at Sandland Adventures, immerse yourself in nature at Darlingtonia State Natural Site, see the interesting displays at Siuslaw Pioneer Museum, and shop like a local with Backstreet Gallery.

To find ratings, photos, other places to visit, and more tourist information, use the Florence online trip builder .

Traveling by car from Bandon to Florence takes 2 hours. Alternatively, you can take a bus. April in Florence sees daily highs of 56°F and lows of 43°F at night. Cap off your sightseeing on the 13th (Fri) early enough to catcht the bus to Eugene.

Things to do in Florence

Parks Nature Outdoors

Side Trips

Elkton, Reedsport, Umpqua River Lighthouse, Oregon Coast, Henry Estate Winery
Highlights from your plan
Oregon Dunes National Recreation Area ©
Umpqua River Lighthouse ©
Umpqua River Lighthouse
Dean Creek Elk Viewing Area ©
Dean Creek Elk Viewing Area

7
nights
Eugene

Eugene ©
Eugene is a city of the Pacific Northwest located in the U.S. Museum-lovers will get to explore Linn County Museum and Dee Wright Observatory. Eschew the tourist crowds and head to Cascades Raptor Center and Willamette River bike trail. You'll find plenty of places to visit near Eugene: Cascadia (Tamolitch Pool Trail & Cascadia State Park), Salt Creek Falls (in Oakridge) and Corvallis (William L. Finley National Wildlife Refuge & Siuslaw National Forest). The adventure continues: learn about winemaking at King Estate Winery and take in the dramatic scenery at McDowell Creek Falls.

For photos, traveler tips, maps, and tourist information, go to the Eugene road trip planner .

You can take a bus from Florence to Eugene in 1.5 hours. Another option is to drive. Expect a daytime high around 61°F in April, and nighttime lows around 40°F. Wrap up your sightseeing on the 20th (Fri) early enough to take a bus to Bend.

Things to do in Eugene

Parks Nature Wildlife

Side Trips

Cascadia, Corvallis, McDowell Creek Falls, Salt Creek Falls, Linn County Historical Museum
Highlights from your plan
Cascades Raptor Center ©
Cascades Raptor Center
Salt Creek Falls ©
Salt Creek Falls
Dee Wright Observatory ©
Dee Wright Observatory

7
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.
You'll explore the less-touristy side of things at Mt. Bachelor Ski Area and Tumalo Falls. Escape the urban bustle at Pilot Butte State Scenic Viewpoint and Deschutes National Forest. You'll find plenty of places to visit near Bend: Tokatee Golf Club (in McKenzie Bridge), Sisters (Sahalie and Koosah Falls, Proxy Falls, & more) and Peter Skene Ogden State Park (in Terrebonne). Next up on the itinerary: contemplate the geological forces at Newberry National Volcanic Monument, tour the pleasant surroundings at Drake Park, explore the fascinating underground world of Lava River Cave, and look for all kinds of wild species at High Desert Museum.

For more things to do, ratings, reviews, and tourist information, you can read our Bend trip itinerary site .

Take a bus from Eugene to Bend in 2.5 hours. Alternatively, you can drive. Expect a bit cooler temperatures when traveling from Eugene in April; daily highs in Bend reach 56°F and lows reach 31°F. Wrap up your sightseeing by early afternoon on the 27th (Fri) to allow time for travel to Baker City.

Things to do in Bend

Parks Nature Outdoors

Side Trips

Sisters, Peter Skene Ogden State Park, Lower Klamath National Wildlife Refuge, Tokatee Golf Club
Highlights from your plan
Pilot Butte State Scenic Viewpoint ©
Pilot Butte State Scenic Viewpoint
Deschutes National  Forest ©
Deschutes National Forest
Newberry National Volcanic Monument ©

2
nights
Baker City

Baker City ©
Baker City is a city in and the county seat of Baker County, Oregon, United States. Start off your visit on the 28th (Sat): get engrossed in the history at Leo Adler House Museum, then take an in-depth tour of Baker Heritage Museum, then take an in-depth tour of National Historic Oregon Trail Interpretive Center, and finally explore the different monuments and memorials at Chinese Cemetery. Here are some ideas for day two: don't miss a visit to Sumpter Valley Dredge.

To find other places to visit, maps, photos, and tourist information, refer to the Baker City sightseeing site .

Traveling by car from Bend to Baker City takes 4.5 hours. In April, daytime highs in Baker City are 59°F, while nighttime lows are 30°F. On the 29th (Sun), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Baker City

Museums Historic Sites

Side Trip

Sumpter Valley Dredge
Highlights from your plan
Baker Heritage Museum ©
Baker Heritage Museum
Leo Adler House Museum ©
Leo Adler House Museum

Similar Plans

60 days in United States BY A USER FROM UNITED STATES November, kids, popular & hidden gems PREFERENCES: November, kids ATTRACTION STYLE: Popular & hidden gems PACE: Medium 60 days in United States BY A USER FROM UNITED STATES June, kids, popular & hidden gems PREFERENCES: June, kids ATTRACTION STYLE: Popular & hidden gems PACE: Medium 60 days in United States BY A USER FROM UNITED KINGDOM February, outdoors, wildlife, hidden gems PREFERENCES: February, outdoors, wildlife ATTRACTION STYLE: Hidden gems PACE: Medium 5 days in Oregon BY A USER FROM UNITED STATES April, teens, kids, popular sights PREFERENCES: April, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium 5 days in Oregon BY A USER FROM UNITED STATES April, teens, hidden gems PREFERENCES: April, teens ATTRACTION STYLE: Hidden gems PACE: Medium 8 days in Oregon BY A USER FROM UNITED STATES June, beaches, historic sites, wildlife, slow & easy, hidden gems PREFERENCES: June, beaches, historic sites, wildlife ATTRACTION STYLE: Hidden gems PACE: Slow & easy 9 days in Oregon BY A USER FROM UNITED STATES June, teens, outdoors, beaches, shopping, popular sights PREFERENCES: June, teens, outdoors, beaches, shopping ATTRACTION STYLE: Popular sights PACE: Medium 9 days in Oregon BY A USER FROM UNITED STATES July, kids, relaxing, beaches, historic sites, wildlife, slow & easy, popular sights PREFERENCES: July, kids, relaxing, beaches, historic sites, wildlife ATTRACTION STYLE: Popular sights PACE: Slow & easy 5 days in Oregon BY A USER FROM CANADA July, teens, popular sights PREFERENCES: July, teens ATTRACTION STYLE: Popular sights PACE: Medium 15 days in Oregon BY A USER FROM UNITED STATES August, teens, kids, outdoors, beaches, historic sites, wildlife, hidden gems PREFERENCES: August, teens, kids, outdoors, beaches, historic sites, wildlife ATTRACTION STYLE: Hidden gems PACE: Medium 5 days in Oregon BY A USER FROM UNITED STATES April, kids, popular sights PREFERENCES: April, kids ATTRACTION STYLE: Popular sights PACE: Medium 8 days in Oregon BY A USER FROM CANADA August, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: August, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium
View more plans