15 days in Oregon Itinerary

15 days in Oregon Itinerary

Created using Inspirock Oregon journey maker

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

Route & dates

15 days in Oregon Itinerary

Start: Detroit
Fly + Drive:  7​h 45​min
1
Timberline Lodge
— Few hours
Drive:  2​h 30​min
2
Bend
— 3 nights
Drive:  3​h 15​min
3
Hood River
— 3 nights
Drive:  3​h
4
Astoria
— 3 nights
Drive:  2​h
5
Portland
— 5 nights
Fly:  7​h 15​min
End: Detroit

few
hours
Timberline Lodge

Timberline Lodge ©
Perched high on the south face of one of the most iconic peaks in the Pacific Northwest, Timberline Lodge is the ski and snowboarding area known for the eponymous historic lodge, the design of which emphasizes the area's natural beauty.
On the 17th (Tue), hit the slopes at Timberline Lodge and Ski Area.

To see more things to do, ratings, where to stay, and other tourist information, use the Timberline Lodge trip itinerary builder site .

Detroit to Timberline Lodge is an approximately 8-hour flight. You can also drive. Due to the time zone difference, you'll gain 3 hours traveling from Detroit to Timberline Lodge. Expect a daytime high around 71°F in September, and nighttime lows around 57°F. Finish up your sightseeing early on the 17th (Tue) so you can travel to Bend.

Things to do in Timberline Lodge

Historic Sites Winter Sports Nature
Highlights from your plan
Timberline Lodge and Ski Area ©
Timberline Lodge and Ski Area

3
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.
Your cultural itinerary includes sights like High Desert Museum and Artists Gallery Sunriver. Get outdoors at Smith Rock State Park and Shevlin Park. Explore Bend's surroundings by going to Sisters (Sahalie and Koosah Falls & McKenzie Pass-Santiam Pass loop) and Dee Wright Observatory (in Blue River). It doesn't end there: take a peaceful walk through Deschutes National Forest and see the sky in a new way at Oregon Observatory.

For photos, traveler tips, more things to do, and more tourist information, go to the Bend itinerary planning site .

You can drive from Timberline Lodge to Bend in 2.5 hours. Traveling from Timberline Lodge in September, expect little chillier with lows of 44°F in Bend. Wrap up your sightseeing on the 20th (Fri) early enough to drive to Hood River.

Things to do in Bend

Parks Nature Museums

Side Trips

Sunriver, Sisters, Smith Rock State Park, Dee Wright Observatory
Highlights from your plan
Smith Rock State Park ©
Smith Rock State Park
High Desert Museum ©
High Desert Museum
Deschutes National  Forest ©
Deschutes National Forest

3
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. Visiting Columbia River Gorge National Scenic Area and Starvation Creek Ridge Loop will get you outdoors. Satisfy your inner culture vulture at Western Antique Aeroplane & Automobile Museum and Columbia Gorge Discovery Center & Museum. Take a break from Hood River with a short trip to Fire Museum in City Hall in The Dalles, about 36 minutes away. And it doesn't end there: trek along Historic Columbia River Highway State Trail, learn about all things military at Fort Dalles Museum and Anderson Homestead, get impressive views of Mount Hood, and do a tasting at Springhouse Cellar.

For other places to visit, where to stay, maps, and more tourist information, use the Hood River road trip planning app .

You can drive from Bend to Hood River in 3.5 hours. Alternatively, you can do a combination of flight and bus; or take a bus. Expect somewhat warmer evenings in Hood River when traveling from Bend in September, with lows around 57°F. Finish your sightseeing early on the 23rd (Mon) so you can drive to Astoria.

Things to do in Hood River

Parks Nature Outdoors

Side Trips

The Dalles, Historic Columbia River Highway State Trail, Columbia River Gorge National Scenic Area, Starvation Creek Ridge Loop
Highlights from your plan
Mount Hood ©
Mount Hood

3
nights
Astoria

Astoria ©
Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
Your cultural itinerary includes sights like Fort Clatsop National Memorial and Columbia River Maritime Museum. Take a break from the city and head to Haystack Rock and Cannon Beach. Step out of Astoria with an excursion to Ecola State Park in Cannon Beach--about 50 minutes away. There's lots more to do: pause for some photo ops at Astoria Column, don't miss a visit to Seaside Beach Lewis and Clark Monument, examine the collection at Seaside Inverted Experience, and get engrossed in the history at Seaside Museum & Historical Society.

To find other places to visit, traveler tips, photos, and other tourist information, use the Astoria tour itinerary planning tool .

Drive from Hood River to Astoria in 3 hours. Alternatively, you can take a bus; or do a combination of train and bus. Expect slightly colder evenings in Astoria when traveling from Hood River in September, with lows around 52°F. Finish your sightseeing early on the 26th (Thu) to allow enough time to drive to Portland.

Things to do in Astoria

Parks Nature Historic Sites

Side Trips

Seaside, Cannon Beach
Highlights from your plan
Haystack Rock ©
Haystack Rock
Ecola State Park ©
Ecola State Park
Cannon Beach ©
Cannon Beach

5
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.
Do some cultural sightseeing at Evergreen Aviation & Space Museum and Portland Art Museum. Escape the urban bustle at Multnomah Falls and The Grotto - National Sanctuary of Our Sorrowful Mother. You'll find plenty of places to visit near Portland: Sokol Blosser Winery (in Dundee) and Multnomah Falls (in Troutdale). There's still lots to do: steep yourself in history at Pittock Mansion, take in nature's colorful creations at Portland Japanese Garden, look for gifts at Powell's City of Books, and tee off at The Reserve Vineyards & Golf Club.

To find reviews, maps, traveler tips, and tourist information, read our Portland holiday planner.

Getting from Astoria to Portland by car takes about 2 hours. Other options: take a bus; or do a combination of bus and train. While traveling from Astoria, expect somewhat warmer days and about the same nights in Portland, ranging from highs of 76°F to lows of 55°F. Wrap up your sightseeing by early afternoon on the 1st (Tue) to allow time for travel back home.

Things to do in Portland

Parks Museums Nature

Side Trips

Evergreen Aviation & Space Museum, Sokol Blosser Winery, Multnomah Falls, The Reserve Vineyards & Golf Club, Columbia River Highway
Highlights from your plan
Portland Japanese Garden ©
Portland Japanese Garden
Multnomah Falls ©
Multnomah Falls
Evergreen Aviation & Space Museum ©
Evergreen Aviation & Space Museum

Similar Plans

11 days in Oregon & Crescent City BY A USER FROM UNITED STATES June, culture, outdoors, relaxing, romantic, beaches, historic sites, wildlife, popular & hidden gems PREFERENCES: June, culture, outdoors, relaxing, romantic, beaches, historic sites, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 16 days in Oregon BY A USER FROM UNITED STATES June, teens, popular & hidden gems PREFERENCES: June, teens ATTRACTION STYLE: Popular & hidden gems PACE: Medium 13 days in Oregon BY A USER FROM UNITED STATES July, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: July, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 16 days in Oregon BY A USER FROM NEW ZEALAND May, popular sights PREFERENCES: May ATTRACTION STYLE: Popular sights PACE: Medium 9 days in Oregon BY A USER FROM UNITED STATES August, teens, kids, outdoors, relaxing, beaches, historic sites, wildlife, slow & easy, popular sights PREFERENCES: August, teens, kids, outdoors, relaxing, beaches, historic sites, wildlife ATTRACTION STYLE: Popular sights PACE: Slow & easy 5 days in Oregon BY A USER FROM UNITED STATES May, relaxing, romantic, beaches, historic sites, shopping, popular & hidden gems PREFERENCES: May, relaxing, romantic, beaches, historic sites, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium 30 days in California, Washington State & Oregon BY A USER FROM UNITED STATES May, culture, outdoors, relaxing, beaches, historic sites, shopping, wildlife, popular & hidden gems PREFERENCES: May, culture, outdoors, relaxing, beaches, historic sites, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 17 days in San Francisco & Oregon BY A USER FROM NETHERLANDS October, popular sights PREFERENCES: October ATTRACTION STYLE: Popular sights PACE: Medium 9 days in Oregon BY A USER FROM BANGLADESH July, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: July, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 20 days in Oregon BY A USER FROM UNITED STATES June, popular & hidden gems PREFERENCES: June ATTRACTION STYLE: Popular & hidden gems PACE: Medium 5 days in Oregon BY A USER FROM UNITED STATES June, teens, outdoors, relaxing, beaches, wildlife, popular & hidden gems PREFERENCES: June, teens, outdoors, relaxing, beaches, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 7 days in Oregon BY A USER FROM UNITED STATES June, outdoors, relaxing, romantic, beaches, historic sites, wildlife, popular sights PREFERENCES: June, outdoors, relaxing, romantic, beaches, historic sites, wildlife ATTRACTION STYLE: Popular sights PACE: Medium
View more plans