14 days in Oregon Itinerary

14 days in Oregon Itinerary

Created using Inspirock Oregon trip planner

Make it your trip
Fly
1
Portland
— 1 night
Drive
2
Newport
— 2 nights
Drive
3
Tillamook
— 2 nights
Drive
4
Astoria
— 6 nights
Drive
5
Hood River
— 2 nights
Fly

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Portland

— 1 night

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.
Start off your visit on the 1st (Fri): see the interesting displays at Evergreen Aviation & Space Museum, contemplate the long history of McLean House, then see the interesting displays at Oregon Museum of Science and Industry, then stop by Powell's City of Books, and finally wander the streets of Northwest (Nob Hill).

To see photos, maps, ratings, and more tourist information, you can read our Portland travel planner.

Asheville to Portland is an approximately 10.5-hour flight. You can also drive; or do a combination of bus and train. The time zone difference when traveling from Asheville to Portland is minus 3 hours. When traveling from Asheville in May, plan for little chillier days in Portland, with highs around 70°F, while nights are about the same with lows around 51°F. On the 2nd (Sat), wrap the sightseeing up by early afternoon so you can drive to Newport.

Things to do in Portland

Museums · Shopping · Historic Sites · Neighborhoods

Side Trips

Newport

— 2 nights
A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
Start off your visit on the 2nd (Sat): enjoy the sand and surf at Devils Punchbowl State Natural Area. Keep things going the next day: visit a coastal fixture at Yaquina Head Lighthouse and then enjoy the sea views from Heceta Head Lighthouse.

To see maps, more things to do, where to stay, and other tourist information, read our Newport travel route planner.

Traveling by car from Portland to Newport takes 3 hours. Alternatively, you can take a bus; or do a combination of train and bus. Expect slightly colder temperatures when traveling from Portland in May; daily highs in Newport reach 58°F and lows reach 46°F. Cap off your sightseeing on the 4th (Mon) early enough to go by car to Tillamook.

Things to do in Newport

Shopping · Museums · Historic Sites · Parks

Side Trips

Tillamook

— 2 nights
The city of Tillamook is the county seat of Tillamook County, Oregon, United States. On the 5th (Tue), contemplate the long history of Tillamook Air Museum, then enjoy the sea views from Cape Meares Lighthouse, then enjoy the sand and surf at Short Sands Beach, and finally kick back and relax at Hug Point State Recreation Site.

To find more things to do, other places to visit, reviews, and tourist information, read Tillamook trip planner.

Drive from Newport to Tillamook in 2 hours. Alternatively, you can take a bus. Due to the time zone difference, you'll lose 1 hour traveling from Newport to Tillamook. In May, daytime highs in Tillamook are 62°F, while nighttime lows are 46°F. Wrap up your sightseeing by early afternoon on the 6th (Wed) to allow enough time to drive to Astoria.

Things to do in Tillamook

Parks · Outdoors · Beaches · Historic Sites

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.
You've added Hanthorn Cannery Museum, Heritage Museum, Museum of Whimsy, and other attractions to your itinerary. You'll get in some beach time at Haystack Rock and Cannon Beach. You'll explore and learn at Columbia River Maritime Museum and Seaside Inverted Experience. Next up on the itinerary: explore the striking landscape of Fort Clatsop National Memorial, pause for some photo ops at Astoria Column, tour the pleasant surroundings at Del Rey Beach State Recreation Site, and steep yourself in history at Lewis & Clark Salt Works.

To see other places to visit, ratings, and more tourist information, you can read our Astoria trip planner.

You can drive from Tillamook to Astoria in 2 hours. Another option is to take a bus. Traveling from Tillamook to Astoria, you'll gain 1 hour due to the time zone difference. In May, daytime highs in Astoria are 62°F, while nighttime lows are 48°F. You'll set off for Hood River on the 12th (Tue).

Things to do in Astoria

Parks · Museums · Nature · Historic Sites

Side Trips

Hood River

— 2 nights
The city of Hood River is the seat of Hood River County, Oregon, United States. Your list of things to see and do now includes Apple Valley Country Store, Foothills Yarn and Fiber, Hood River Lavender Farms, and other attractions. Start off your visit on the 12th (Tue): see the interesting displays at Columbia Gorge Discovery Center & Museum, then get engrossed in the history at Fort Dalles Museum and Anderson Homestead, and then examine the collection at Western Antique Aeroplane & Automobile Museum. Keep things going the next day: stop by Apple Valley Country Store, look for gifts at Foothills Yarn and Fiber, relax in the rural setting at Hood River Lavender Farms, then shop like a local with Lavender Valley, and finally stop by Art on Oak.

To find where to stay, photos, ratings, and other tourist information, read our Hood River journey planner.

You can drive from Astoria to Hood River in 3 hours. Alternatively, you can take a bus; or do a combination of bus and train. In May in Hood River, expect temperatures between 67°F during the day and 49°F at night. Cap off your sightseeing on the 14th (Thu) early enough to travel back home.

Things to do in Hood River

Shopping · Museums

Side Trip

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.