38 days in Oregon Itinerary

38 days in Oregon Itinerary

Created using Inspirock Oregon attractions planner
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1
Ashland
— 4 nights
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2
Crater Lake National Park
— 3 nights
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3
Bend
— 3 nights
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4
Portland
— 6 nights
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5
Astoria
— 3 nights
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6
Tillamook
— 2 nights
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Salem
— 2 nights
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Newport
— 4 nights
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Florence
— 4 nights
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Eugene
— 4 nights
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Ashland — 4 nights

Ashland is a city in Jackson County, in the State of Oregon. You'll explore the less-touristy side of things at Mt. Ashland Ski Area and Dana Campbell Vineyards. There's much more to do: stroll around Lithia Park, see a show at Oregon Shakespeare Festival, do a tasting at Grizzly Peak Winery, and take in the exciting artwork at Gathering Glass Studio.

To find maps, more things to do, other places to visit, and more tourist information, you can read our Ashland itinerary maker.

Palmdale to Ashland is an approximately 5.5-hour combination of car and flight. You can also drive. When traveling from Palmdale in January, plan for little chillier days and about the same nights in Ashland: temperatures range from 49°F by day to 32°F at night. Wrap up your sightseeing on the 5th (Wed) early enough to drive to Crater Lake National Park.
Parks · Winter Sports · Outdoors · Shopping

Crater Lake National Park — 3 nights

Reaching a depth of 592 m (1,943 ft), Crater Lake is the deepest lake in the United States.
Eschew the tourist crowds and head to Wizard Island and Whitehorse Falls. And it doesn't end there: take in the dramatic scenery at Toketee Falls, trek along Sun Notch Trail, and tour the pleasant surroundings at Annie Creek Canyon.

To find where to stay, maps, ratings, and more tourist information, you can read our Crater Lake National Park trip itinerary planner.

Getting from Ashland to Crater Lake National Park by car takes about 2 hours. Other options: do a combination of bus and taxi. In January, daily temperatures in Crater Lake National Park can reach 49°F, while at night they dip to 32°F. Finish your sightseeing early on the 9th (Sun) to allow enough time to drive to Bend.
Parks · Outdoors · Trails · Nature

Bend — 3 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.
You'll discover tucked-away gems like Mt. Bachelor Ski Area and Boneyard Beer. Get out of town with these interesting Bend side-trips: Peter Skene Ogden State Park (in Terrebonne) and Smith Rock State Park (in Redmond). There's lots more to do: contemplate the waterfront views at Todd Lake, grab your bike and head to Deschutes River Trail, fly down the slopes at Oregon Trail of Dreams, and sample the tasty concoctions at Atlas Cider Co.

For other places to visit, maps, photos, and more tourist information, read our Bend tour itinerary builder site.

You can drive from Crater Lake National Park to Bend in 2.5 hours. Alternatively, you can do a combination of taxi and bus. Traveling from Crater Lake National Park in January, expect Bend to be slightly colder, temps between 42°F and 24°F. Finish your sightseeing early on the 12th (Wed) to allow enough time to fly to Portland.
Parks · Outdoors · Nature · Breweries & Distilleries
Side Trips

Portland — 6 nights

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.
You'll explore the less-touristy side of things at St. Johns Bridge and Tryon Creek State Natural Area. Step out of Portland to go to Corbett and see Vista House, which is approximately 36 minutes away. There's still lots to do: look for gifts at Powell's City of Books, take in nature's colorful creations at Portland Japanese Garden, surround yourself with nature on Volcano Lands - Private Tours, and examine the collection at Oregon Museum of Science and Industry.

To see ratings, traveler tips, maps, and tourist information, you can read our Portland trip itinerary builder site.

Getting from Bend to Portland by flight takes about 2.5 hours. Other options: drive; or take a bus. Plan for a bit warmer nights when traveling from Bend in January since evenings lows in Portland dip to 35°F. Finish up your sightseeing early on the 18th (Tue) so you can go by car to Astoria.
Parks · Museums · Outdoors · Shopping
Side Trips

Astoria — 3 nights

Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
Eschew the tourist crowds and head to Seaside Beach and Shallon Winery. Take a break from Astoria with a short trip to Cannon Beach in Cannon Beach, about 44 minutes away. There's much more to do: immerse yourself in nature at Fort Stevens State Park, enjoy the sea views from Lightship Columbia, explore the activities along Clatsop Spit, and tour the pleasant surroundings at Astoria Column.

To find ratings, maps, reviews, and tourist information, you can read our Astoria online holiday maker.

Traveling by car from Portland to Astoria takes 2 hours. Alternatively, you can take a bus. January in Astoria sees daily highs of 50°F and lows of 38°F at night. Finish your sightseeing early on the 21st (Fri) to allow enough time to drive to Tillamook.
Parks · Outdoors · Beaches · Nature
Side Trips

Tillamook — 2 nights

The city of Tillamook is the county seat of Tillamook County, Oregon, United States. Start off your visit on the 22nd (Sat): admire the majestic nature at Bob Straub State Park and then sample the tasty concoctions at De Garde Brewing. Get ready for a full day of sightseeing on the next day: visit a coastal fixture at Cape Meares Lighthouse and then take in the waterfront at Garibaldi Boat Basin.

For ratings, traveler tips, where to stay, and more tourist information, read our Tillamook road trip planning tool.

You can drive from Astoria to Tillamook in 2 hours. Alternatively, you can take a bus. The time zone changes from Pacific Standard Time to Mountain Standard Time, which is usually a 1 hour difference. In January, daytime highs in Tillamook are 51°F, while nighttime lows are 36°F. Finish up your sightseeing early on the 23rd (Sun) so you can go by car to Salem.
Breweries & Distilleries · Historic Sites · Parks · Nature
Side Trips

Salem — 2 nights

Salem is the capital of the U.S. state of Oregon, and the county seat of Marion County. Start off your visit on the 24th (Mon): get a tailor-made plan with Prestige Wine Tours and then experience rural life at Willamette Valley Fruit Company. Here are some ideas for day two: examine the collection at Evergreen Aviation & Space Museum.

For more things to do, photos, and other tourist information, go to the Salem trip tool.

Drive from Tillamook to Salem in 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. Traveling from Tillamook to Salem, you'll gain 1 hour due to the time zone difference. In January, plan for daily highs up to 47°F, and evening lows to 35°F. Wrap up your sightseeing on the 25th (Tue) to allow time to drive to Newport.
Museums · Tours · Wineries
Side Trip

Newport — 4 nights

A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
Step off the beaten path and head to Nye Beach and Siletz Bay Park. Explore Newport's surroundings by going to Lincoln City (Mossy Creek Pottery, Beachtown Charities Thrift and Gift, &more). The adventure continues: take in the waterfront at Newport's Historic Bayfront, enjoy the sea views from Yaquina Head Lighthouse, and stroll through Yaquina Head Outstanding Natural Area.

For reviews, photos, maps, and tourist information, go to the Newport trip itinerary maker.

Traveling by car from Salem to Newport takes 2 hours. Alternatively, you can take a bus. In January in Newport, expect temperatures between 51°F during the day and 40°F at night. Cap off your sightseeing on the 29th (Sat) early enough to go by car to Florence.
Parks · Casinos · Fun & Games · Wildlife
Side Trip

Florence — 4 nights

Florence is a coastal city in Lane County, in the U.S. state of Oregon. Explore hidden gems such as Bullards Beach State Park and Ocean Dunes Golf Links. Get out of town with these interesting Florence side-trips: Second Street Gallery (in Bandon) and Cape Perpetua Visitor Center - Siuslaw National Forest (in Yachats). Next up on the itinerary: visit a coastal fixture at Heceta Head Lighthouse, cruise along Oregon Route 38, see Sandland Adventures, and play a few rounds at Florence Golf Links.

For other places to visit, maps, where to stay, and other tourist information, go to the Florence day trip planner.

Drive from Newport to Florence in 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 55°F in January, and nighttime lows around 40°F. Wrap up your sightseeing on the 2nd (Wed) early enough to drive to Eugene.
Outdoors · Golf · Parks · Nature
Side Trips

Eugene — 4 nights

Eugene is a city of the Pacific Northwest located in the U.S. state of Oregon. Eschew the tourist crowds and head to Cascades Raptor Center and King Estate Winery. There's still lots to do: hike along Mt Pisgah, stroll around Hendricks Park, do a tasting at Sarver Winery, and gain insight at University of Oregon.

To see other places to visit, traveler tips, reviews, and tourist information, refer to the Eugene trip planning tool.

You can drive from Florence to Eugene in 1.5 hours. Alternatively, you can take a bus. Expect slightly colder evenings in Eugene when traveling from Florence in February, with lows around 37°F. Finish up your sightseeing early on the 6th (Sun) so you can travel back home.
Wineries · Parks · Outdoors · Trails

Oregon travel guide

4.5
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.