7 days in Oregon Itinerary

7 days in Oregon Itinerary

Created using Inspirock Oregon trip itinerary builder

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Route & dates

7 days in Oregon Itinerary

Start: Houston
Fly:  8​h 15​min
1
Redmond
— 4 nights
Drive:  2​h 15​min
2
Timberline Lodge
— 1 night
Drive:  1​h 30​min
3
Portland
— 1 night
Fly:  6​h 45​min
End: Houston

4
nights
Redmond

Redmond ©
Redmond is a city in Deschutes County, Oregon, United States. Start off your visit on the 22nd (Wed): wander the streets of City of Sisters and then stop by Crescent Moon Ranch.

For traveler tips, more things to do, ratings, and other tourist information, read Redmond sightseeing planner.

New York City to Redmond is an approximately 9.5-hour flight. You can also drive. You'll gain 3 hours traveling from New York City to Redmond due to the time zone difference. Traveling from New York City in May, expect a bit cooler with lows of 37°F in Redmond. Finish your sightseeing early on the 23rd (Thu) so you can travel to Timberline Lodge.

Things to do in Redmond

Outdoors Golf Parks

Side Trips

Crescent Moon Ranch, City of Sisters
Highlights from your plan
Eagle Crest Resort Golf Courses ©
Eagle Crest Resort Golf Courses
Crescent Moon Ranch ©
Crescent Moon Ranch
City of Sisters ©
City of Sisters

1
night
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.
Start off your visit on the 30th (Thu): fly down the slopes at Timberline Lodge and Ski Area and then take a peaceful walk through Mt. Hood National Forest.

Start your trip to Timberline Lodge by creating a personalized itinerary on Inspirock.

Getting from Redmond to Timberline Lodge by car takes about 2 hours. Plan for somewhat warmer nights when traveling from Redmond in May since evenings lows in Timberline Lodge dip to 49°F. Wrap up your sightseeing on the 31st (Fri) to allow time to travel to Portland.

Things to do in Timberline Lodge

Nature Parks Winter Sports

Side Trip

Mt. Hood National Forest
Highlights from your plan
Timberline Lodge and Ski Area ©
Timberline Lodge and Ski Area
Mt. Hood National Forest ©
Mt. Hood National Forest

1
night
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.
Start off your visit on the 31st (Fri): steep yourself in history at Pittock Mansion, then admire the natural beauty at Portland Japanese Garden, then admire the natural beauty at International Rose Test Garden, and finally wander the streets of Northwest (Nob Hill).

Start your trip to Portland by creating a personalized itinerary on Inspirock.

Getting from Timberline Lodge to Portland by car takes about 1.5 hours. May in Portland sees daily highs of 70°F and lows of 51°F at night. You'll have a few hours on the 1st (Sat) to wrap things up before traveling home.

Things to do in Portland

Shopping Parks Neighborhoods
Highlights from your plan
Powell's City of Books ©
Powell's City of Books
Northwest (Nob Hill) ©
Northwest (Nob Hill)
Portland Japanese Garden ©
Portland Japanese Garden

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