11 days in Oregon Itinerary

11 days in Oregon Itinerary

Created using Inspirock Oregon route maker

Make it your trip
Fly
1
Portland
— 2 nights
Drive
2
Cannon Beach
— 2 nights
Drive
3
Hood River
— 2 nights
Drive
4
Bend
— 1 night
Drive
5
Crater Lake National Park
— 1 night
Drive
6
Ashland
— 2 nights
Fly

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Portland

— 2 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.
Get out of town with these interesting Portland side-trips: Multnomah Falls (in Bridal Veil) and Evergreen Aviation & Space Museum (in McMinnville). There's much more to do: admire the natural beauty at International Rose Test Garden, learn the secrets of beer at a beer tour and tasting, learn about wildlife with up-close encounters at Oregon Zoo, and look for gifts at Powell's City of Books.

For other places to visit, photos, where to stay, and other tourist information, go to the Portland day trip tool.

Boston to Portland is an approximately 8-hour flight. You can also drive; or take a train. You'll gain 3 hours traveling from Boston to Portland due to the time zone difference. Traveling from Boston in July, you can expect nighttime temperatures to be little chillier in Portland, with lows of 59°F. Finish your sightseeing early on the 4th (Sun) to allow enough time to drive to Cannon Beach.

Things to do in Portland

Parks · Breweries & Distilleries · Tours · Museums

Side Trips

Cannon Beach

— 2 nights
Cannon Beach is a city in Clatsop County, Oregon, United States. On the 5th (Mon), kick back and relax at Haystack Rock, stroll through Cannon Beach, then look for gifts at Cloud and Leaf Bookstore, and finally admire the majestic nature at Ecola State Park. On the 6th (Tue), you'll have a packed day of sightseeing: admire the majestic nature at Hug Point State Park, tour the pleasant surroundings at Manzanita Beach, then tour the pleasant surroundings at Cedar Wetlands Preserve, and finally immerse yourself in nature at Oswald West State Park.

To find where to stay, ratings, and other tourist information, use the Cannon Beach trip planner.

Traveling by car from Portland to Cannon Beach takes 1.5 hours. Alternatively, you can take a bus. Traveling from Portland in July, you will find days in Cannon Beach are a bit cooler (69°F), and nights are about the same (55°F). Finish your sightseeing early on the 6th (Tue) so you can drive to Hood River.

Things to do in Cannon Beach

Parks · Nature · Outdoors · Beaches

Side Trips

Hood River

— 2 nights
The city of Hood River is the seat of Hood River County, Oregon, United States. Kick off your visit on the 7th (Wed): look for all kinds of wild species at Columbia River Gorge National Scenic Area, then stroll through Historic Columbia River Highway State Trail, and then don't miss a visit to The Dalles Murals. Keep things going the next day: examine the collection at Western Antique Aeroplane & Automobile Museum, then explore and take pictures at Hood River County Fruit Loop, and then get impressive views of Mount Hood.

To see reviews, where to stay, other places to visit, and more tourist information, read our Hood River trip maker website.

Drive from Cannon Beach to Hood River in 3 hours. Alternatively, you can take a bus; or do a combination of bus and train. When traveling from Cannon Beach in July, plan for somewhat warmer days in Hood River, with highs around 79°F, while nights are about the same with lows around 58°F. Wrap up your sightseeing on the 8th (Thu) early enough to fly to Bend.

Things to do in Hood River

Parks · Outdoors · Nature · Wildlife

Side Trips

Bend

— 1 night
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.
Kick off your visit on the 9th (Fri): walk around Drake Park, take a memorable tour with Tours, then explore the activities along Deschutes River, and finally explore the wealth of natural beauty at Deschutes National Forest.

To find traveler tips, where to stay, other places to visit, and other tourist information, refer to the Bend trip itinerary maker website.

Traveling by flight from Hood River to Bend takes 2.5 hours. Alternatively, you can drive; or take a bus. When traveling from Hood River in July, plan for somewhat warmer days in Bend, with highs around 85°F, while nights are slightly colder with lows around 52°F. Finish up your sightseeing early on the 9th (Fri) so you can go by car to Crater Lake National Park.

Things to do in Bend

Parks · Nature · Tours · Outdoors

Crater Lake National Park

— 1 night
Reaching a depth of 592 m (1,943 ft), Crater Lake is the deepest lake in the United States.
Start off your visit on the 10th (Sat): explore the wealth of natural beauty at Crater Lake National Park.

To find where to stay, maps, more things to do, and more tourist information, go to the Crater Lake National Park trip itinerary planner.

Traveling by car from Bend to Crater Lake National Park takes 2.5 hours. Alternatively, you can do a combination of bus and taxi. Traveling from Bend in July, expect Crater Lake National Park to be somewhat warmer, temps between 94°F and 61°F. Wrap up your sightseeing on the 10th (Sat) early enough to drive to Ashland.

Things to do in Crater Lake National Park

Parks · Nature
Highlights from your trip

Ashland

— 2 nights
Ashland is a city in Jackson County, in the State of Oregon. Start off your visit on the 11th (Sun): walk around Lithia Park, then see a show at Oregon Shakespeare Festival, and then let the river carry you with a rafting and tubing tour.

To find other places to visit, traveler tips, and more tourist information, use the Ashland travel itinerary planner.

You can drive from Crater Lake National Park to Ashland in 2 hours. Alternatively, you can do a combination of taxi and bus. July in Ashland sees daily highs of 94°F and lows of 61°F at night. Finish your sightseeing early on the 12th (Mon) so you can fly back home.

Things to do in Ashland

Tours · Parks · Outdoors · Nightlife

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.