60 days in Oregon Itinerary

60 days in Oregon Itinerary

Created using Inspirock Oregon trip itinerary maker

Make it your trip
Fly
1
Bend
— 6 nights
Fly
2
Hood River
— 6 nights
Drive
3
Portland
— 8 nights
Drive
4
Astoria
— 6 nights
Drive
5
Tillamook
— 5 nights
Drive
6
Newport
— 6 nights
Drive
7
Florence
— 6 nights
Drive
8
Coos Bay
— 5 nights
Drive
9
Brookings
— 4 nights
Drive
10
Eugene
— 7 nights
Fly

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Bend

— 6 nights
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.
Eschew the tourist crowds and head to Tumalo Falls and The Art of Alfred A. Dolezal Gallery. Get out of town with these interesting Bend side-trips: Sisters (Sahalie and Koosah Falls & City of Sisters), Brasada Ranch (in Powell Butte) and Smith Rock State Park (in Redmond). Next up on the itinerary: hike along Pilot Butte State Scenic Viewpoint, see what you can catch with a fishing tour, contemplate the geological forces at Newberry National Volcanic Monument, and admire the majestic nature at Tumalo State Park.

To see photos, where to stay, and other tourist information, read Bend road trip planning tool.

Charleston to Bend is an approximately 9.5-hour flight. You can also drive; or do a combination of bus and train. You'll gain 3 hours traveling from Charleston to Bend due to the time zone difference. In November, Bend is colder than Charleston - with highs of 48°F and lows of 28°F. Wrap up your sightseeing on the 26th (Fri) early enough to fly to Hood River.

Things to do in Bend

Parks · Nature · Outdoors · Trails

Side Trips

Find places to stay Nov 20 — 26:
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Hood River

— 6 nights
The city of Hood River is the seat of Hood River County, Oregon, United States. You'll discover tucked-away gems like Western Antique Aeroplane & Automobile Museum and Cathedral Ridge Winery. Get out of town with these interesting Hood River side-trips: Trillium Lake (in Government Camp) and Bonneville Lock & Dam (in Cascade Locks). There's lots more to do: contemplate the waterfront views at Columbia River Gorge National Scenic Area, stroll through Bonneville Hatchery, snap pictures at Bridge of the Gods, and examine the collection at Columbia Gorge Discovery Center & Museum.

For photos, other places to visit, and more tourist information, go to the Hood River trip planner.

Getting from Bend to Hood River by flight takes about 2.5 hours. Other options: drive; or take a bus. Traveling from Bend in November, expect somewhat warmer with lows of 36°F in Hood River. Cap off your sightseeing on the 2nd (Thu) early enough to go by car to Portland.

Things to do in Hood River

Parks · Outdoors · Nature · Trails

Side Trips

Find places to stay Nov 26 — Dec 2:
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Portland

— 8 nights

City of Roses

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 hidden gems such as Volcano Lands - Private Tours and Vista House. Explore the numerous day-trip ideas around Portland: The Oregon Garden (in Silverton), Silver Falls State Park (in Drake Crossing) and Evergreen Aviation & Space Museum (in McMinnville). There's much more to do: look for gifts at Powell's City of Books, admire the striking features of Pittock Mansion, admire the verdant scenery at Willamette Valley, and admire the sheer force of Multnomah Falls.

For traveler tips, reviews, more things to do, and more tourist information, go to the Portland driving holiday planner.

Drive from Hood River to Portland in 1.5 hours. Alternatively, you can take a bus; or take a train. In December, daily temperatures in Portland can reach 45°F, while at night they dip to 35°F. Cap off your sightseeing on the 10th (Fri) early enough to go by car to Astoria.

Things to do in Portland

Parks · Tours · Nature · Outdoors

Side Trips

Find places to stay Dec 2 — 10:
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Astoria

— 6 nights

Spirit of the Columbia

Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
Explore hidden gems such as Fort Clatsop National Memorial and Camp 18 Logging Museum & Restaurant. Get out of town with these interesting Astoria side-trips: Cannon Beach (Hug Point State Park, Icefire Glassworks, &more) and Turnaround at Seaside (in Seaside). Next up on the itinerary: trek along Astoria Oregon Riverwalk, examine the collection at Flavel House Museum, contemplate the waterfront views at Columbia River Maritime Museum, and pause for some photo ops at Astoria Column.

To find traveler tips, maps, other places to visit, and other tourist information, use the Astoria tour planner.

Getting from Portland to Astoria by car takes about 2 hours. Other options: take a bus. In December, daily temperatures in Astoria can reach 49°F, while at night they dip to 37°F. Wrap up your sightseeing on the 16th (Thu) early enough to drive to Tillamook.

Things to do in Astoria

Parks · Nature · Museums · Outdoors

Side Trips

Find places to stay Dec 10 — 16:
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Tillamook

— 5 nights
The city of Tillamook is the county seat of Tillamook County, Oregon, United States. Step off the beaten path and head to Oswald West State Park and Spas. You'll find plenty of places to visit near Tillamook: Nehalem Bay State Park (in Nehalem), Kelly's Brighton Marina (in Rockaway Beach) and Manzanita Beach (in Manzanita). There's lots more to do: enjoy the sea views from Cape Meares Lighthouse, see the interesting displays at Tillamook Air Museum, kick back and relax at Rockaway Beach Wayside, and admire the majestic nature at Cape Lookout State Park.

To find maps, photos, reviews, and other tourist information, read our Tillamook day trip site.

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 December, daytime highs in Tillamook are 49°F, while nighttime lows are 36°F. Wrap up your sightseeing on the 21st (Tue) early enough to drive to Newport.

Things to do in Tillamook

Parks · Outdoors · Nature · Beaches

Side Trips

Find places to stay Dec 16 — 21:
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Newport

— 6 nights
A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
Discover out-of-the-way places like Prehistoric and Cape Foulweather. Explore Newport's surroundings by going to Lincoln City (Lincoln City Glass Center, Beachtown Charities Thrift and Gift, &more), Yachats coastline (in Yachats) and Drift Creek Falls Trail (in Otis). Next up on the itinerary: don't miss a visit to Yaquina Bay Bridge, admire the majestic nature at South Beach State Park, get up close to creatures of the deep with a dolphin and whale watching tour, and enjoy the sand and surf at Nye Beach.

For more things to do and more tourist information, go to the Newport trip builder.

Traveling by car from Tillamook to Newport takes 2 hours. Alternatively, you can take a bus. Due to the time zone difference, you'll gain 1 hour traveling from Tillamook to Newport. In December in Newport, expect temperatures between 49°F during the day and 39°F at night. Finish up your sightseeing early on the 27th (Mon) so you can go by car to Florence.

Things to do in Newport

Parks · Museums · Outdoors · Nature

Side Trips

Find places to stay Dec 21 — 27:
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Florence

— 6 nights
Florence is a coastal city in Lane County, in the U.S. state of Oregon. You'll discover tucked-away gems like Hobbit Trail and Siuslaw River Bridge. Explore Florence's surroundings by going to Dean Creek Elk Viewing Area (in Reedsport) and Yachats (Cape Perpetua Visitor Center - Siuslaw National Forest & Devil's Churn). There's still lots to do: take in the dramatic natural features at Thor's Well, tee off at Ocean Dunes Golf Links, admire the majestic nature at Darlingtonia State Natural Site, and kick back and relax at Heceta Beach.

To see photos, ratings, maps, and tourist information, you can read our Florence trip planner.

Getting from Newport to Florence by car takes about 1.5 hours. Other options: take a bus. December in Florence sees daily highs of 53°F and lows of 40°F at night. Cap off your sightseeing on the 2nd (Sun) early enough to go by car to Coos Bay.

Things to do in Florence

Parks · Outdoors · Nature · Scenic Drive

Side Trips

Find places to stay Dec 27 — Jan 2:
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Coos Bay

— 5 nights
Coos Bay is a city located in Coos County, Oregon, United States, where the Coos River enters Coos Bay on the Pacific Ocean. You'll discover tucked-away gems like Cape Arago State Park and Face Rock State Scenic Viewpoint. You'll find plenty of places to visit near Coos Bay: Cape Blanco Lighthouse (in Port Orford), Oregon Dunes National Recreation Area (in Reedsport) and Bandon (Face Rock Creamery, Second Street Gallery, &more). There's still lots to do: immerse yourself in nature at Shore Acres State Park and tee off at Bandon Dunes Golf Resort.

To find other places to visit, reviews, where to stay, and tourist information, refer to the Coos Bay day trip planning app.

You can drive from Florence to Coos Bay in 1.5 hours. In January, plan for daily highs up to 55°F, and evening lows to 40°F. Finish your sightseeing early on the 7th (Fri) to allow enough time to travel to Brookings.

Things to do in Coos Bay

Nature · Parks · Historic Sites · Shopping

Side Trips

Find places to stay Jan 2 — 7:
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Brookings

— 4 nights
Brookings is a city in Curry County, Oregon, United States. You'll explore the less-touristy side of things at Harris Beach State Park and Otter Point State Recreation Site. Change things up with these side-trips from Brookings: Gold Beach (Rogue River Bridge & The Mary D Hume) and Oregon Caves National Monument and Preserve (in Cave Junction). The adventure continues: enjoy the sand and surf at Lone Ranch Beach, explore and take pictures at Samuel H. Boardman State Scenic Corridor, walk around Azalea Park, and admire the majestic nature at Alfred A Loeb State Park.

Plan my trip to Brookings with suggested itineraries provided by Inspirock.

Traveling by car from Coos Bay to Brookings takes 2.5 hours. Expect a daytime high around 54°F in January, and nighttime lows around 41°F. Finish your sightseeing early on the 11th (Tue) to allow enough time to travel to Eugene.

Things to do in Brookings

Parks · Nature · Outdoors · Scenic Drive

Side Trips

Find places to stay Jan 7 — 11:
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Eugene

— 7 nights
Eugene is a city of the Pacific Northwest located in the U.S. state of Oregon. Eschew the tourist crowds and head to University of Oregon and Willamette River Trail. Explore the numerous day-trip ideas around Eugene: The Historic Carousel and Museum (in Albany), Oregon State University (in Corvallis) and Roseburg (Watson Falls & Abacela). And it doesn't end there: hunt for treasures at Eugene Saturday Market, hike along Mt Pisgah, tour the pleasant surroundings at Wildlife Safari, and sample the tasty concoctions at The Better Living Room by Ninkasi Brewing.

To see maps, other places to visit, and more tourist information, you can read our Eugene tour planner.

Traveling by car from Brookings to Eugene takes 4.5 hours. Traveling from Brookings in January, expect Eugene to be slightly colder, temps between 47°F and 34°F. On the 18th (Tue), you'll travel back home.

Things to do in Eugene

Parks · Outdoors · Trails · Wineries

Side Trips

Find places to stay Jan 11 — 18:
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Oregon travel guide

4.5
A land of many faces, Oregon is at once a state of rugged rocky coastlines and deep forests, as well as vibrant cities and small towns packed with award-winning restaurants and trendy shops. With nearly half of its land covered by dense fir, redwood, and pine forests, the state protects varied plant and animal life inside three national parks. In addition to pristine waterfalls, beaches, and lakes perfect for a holiday in nature, Oregon also offers numerous urban tourist attractions. Portland, the state's largest metropolis, notably includes more breweries than any other city in the world, and its central location makes it an ideal base for day trips to Oregon's emerging wine region and many parks.