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 Pilot Butte State Scenic Viewpoint. Get out of town with these interesting Bend side-trips: Smith Rock State Park (in Redmond), Brasada Ranch (in Powell Butte) and Sisters (Sahalie and Koosah Falls & City of Sisters). Next up on the itinerary: contemplate the geological forces at Newberry National Volcanic Monument, see what you can catch with a fishing tour, take in the exciting artwork at The Art of Alfred A. Dolezal Gallery, 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 · Tours

Side Trips

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 Columbia Gorge Discovery Center & Museum. 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 still lots to do: explore the activities along Columbia River Gorge National Scenic Area, tour the pleasant surroundings at Bonneville Hatchery, learn about winemaking at Cathedral Ridge Winery, and contemplate the geological forces at Mount Hood.

To find ratings, other places to visit, where to stay, and tourist information, read Hood River holiday maker app.

Fly from Bend to Hood River in 2.5 hours. Alternatively, you can drive; or take a bus. Traveling from Bend in November, Hood River is a bit warmer at night with lows of 36°F. 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 · Wineries

Side Trips

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 Willamette Valley. Explore the numerous day-trip ideas around Portland: Silver Falls State Park (in Drake Crossing), The Oregon Garden (in Silverton) 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, awaken your taste buds at Cellar Door Wine Tours, 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

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 Astoria Oregon Riverwalk. Get out of town with these interesting Astoria side-trips: Seaside (Turnaround at Seaside & Camp 18 Logging Museum & Restaurant) and Cannon Beach (Hug Point State Park, Icefire Glassworks, &more). There's lots more to do: explore the activities along Columbia River Maritime Museum, pause for some photo ops at Astoria Column, examine the collection at Flavel House Museum, and admire the majestic nature at Fort Stevens State Park.

For more things to do, where to stay, and more tourist information, use the Astoria trip planner.

Drive from Portland to Astoria in 2 hours. Alternatively, you can take a bus. December in Astoria sees daily highs of 49°F and lows of 37°F at night. Wrap up your sightseeing on the 16th (Thu) to allow time to drive to Tillamook.

Things to do in Astoria

Parks · Nature · Museums · Outdoors

Side Trips

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 Cape Lookout State Park. 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 (Manzanita Beach & Spas). There's lots more to do: enjoy the sea views from Cape Meares Lighthouse, stroll through Rockaway Beach Wayside, contemplate the long history of Tillamook Air Museum, and enjoy the sand and surf at Cape Kiwanda State Natural Area.

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 · Beaches · Outdoors · Nature

Side Trips

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 Drift Creek Falls Trail. Explore Newport's surroundings by going to Lincoln City (Lincoln City Glass Center, Beachtown Charities Thrift and Gift, &more) and Yachats coastline (in Yachats). There's still lots to do: make a trip to Yaquina Bay Bridge, explore the striking landscape at Cape Foulweather, admire the majestic nature at South Beach State Park, and stroll through Yaquina Head Outstanding Natural Area.

To see other places to visit, reviews, and more tourist information, go to the Newport day trip site.

Traveling by car from Tillamook to Newport takes 2 hours. Alternatively, you can take a bus. The time zone difference moving from Mountain Standard Time (MST) to Pacific Standard Time (PST) is minus 1 hour. December in Newport sees daily highs of 49°F and lows of 39°F at night. Finish your sightseeing early on the 27th (Mon) so you can drive to Florence.

Things to do in Newport

Parks · Museums · Outdoors · Nature

Side Trips

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 Thor's Well. 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 much more to do: admire the majestic nature at Darlingtonia State Natural Site, take in the views from Siuslaw River Bridge, Head underground at Sea Lion Caves, and admire all the interesting features of Oregon Coast Hwy.

To see ratings, traveler tips, maps, and other tourist information, read our Florence online tour itinerary planner.

You can drive from Newport to Florence in 1.5 hours. Another option is to take a bus. In December, plan for daily highs up to 53°F, and evening lows to 40°F. Finish up your sightseeing early on the 2nd (Sun) so you can go by car to Coos Bay.

Things to do in Florence

Parks · Outdoors · Nature · Scenic Drive

Side Trips

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 Shore Acres State Park. You'll find plenty of places to visit near Coos Bay: Cape Blanco Lighthouse (in Port Orford), Bandon (Face Rock Creamery, Face Rock State Scenic Viewpoint, &more) and Oregon Dunes National Recreation Area (in Reedsport). There's more to do: tee off at Bandon Dunes Golf Resort.

To see other places to visit, reviews, where to stay, and more tourist information, read our Coos Bay driving holiday website.

Traveling by car from Florence to Coos Bay takes 1.5 hours. Expect a daytime high around 55°F in January, and nighttime lows around 40°F. Cap off your sightseeing on the 7th (Fri) early enough to travel to Brookings.

Things to do in Coos Bay

Parks · Nature · Historic Sites · Shopping

Side Trips

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 Samuel H. Boardman State Scenic Corridor. Change things up with these side-trips from Brookings: Oregon Caves National Monument and Preserve (in Cave Junction) and Gold Beach (Rogue River Bridge, Otter Point State Recreation Site, &more). The adventure continues: enjoy the sand and surf at Lone Ranch Beach, stroll around Azalea Park, and admire the majestic nature at Alfred A Loeb State Park.

To see photos, maps, other places to visit, and tourist information, you can read our Brookings road trip site.

Traveling by car from Coos Bay to Brookings takes 2.5 hours. In January, daytime highs in Brookings are 54°F, while nighttime lows are 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 · Beaches

Side Trips

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 The Historic Carousel and Museum. Explore the numerous day-trip ideas around Eugene: Wildlife Safari (in Winston), Oregon State University (in Corvallis) and Roseburg (Watson Falls & Abacela). The adventure continues: explore the landscape on two wheels at Willamette River Trail, get outside with Spencer Butte, sample the tasty concoctions at The Better Living Room by Ninkasi Brewing, and trek along Mt Pisgah.

To find maps, where to stay, more things to do, and tourist information, use the Eugene trip maker website.

Traveling by car from Brookings to Eugene takes 4.5 hours. Expect little chillier temperatures when traveling from Brookings in January; daily highs in Eugene reach 47°F and lows reach 34°F. On the 18th (Tue), you're off to home.

Things to do in Eugene

Parks · Outdoors · Trails · Wineries

Side Trips

Oregon travel guide

4.4
Gardens · State Parks · Specialty Museums
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.