11 days in Oregon Itinerary

Ashland is a city in Jackson County, in the State of Oregon. Kick off your visit on the 11th (Sat): take a memorable tour with Tours, then walk around Lithia Park, and then explore the activities along Rogue River.

To see traveler tips, photos, more things to do, and other tourist information, go to the Ashland attractions planner.

New York City to Ashland is an approximately 12-hour flight. You can also drive; or do a combination of train and bus. Due to the time zone difference, you'll gain 3 hours traveling from New York City to Ashland. While traveling from New York City, expect somewhat warmer days and slightly colder nights in Ashland, ranging from highs of 94°F to lows of 61°F. Wrap up your sightseeing on the 11th (Sat) to allow time to drive to Crater Lake National Park.

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 12th (Sun): explore the striking landscape of Crater Lake National Park.

Planning Crater Lake National Park trip won't be overwhelming when you use Inspirock's itinerary maker.

You can drive from Ashland to Crater Lake National Park in 2 hours. Alternatively, you can do a combination of bus and taxi. In July, daytime highs in Crater Lake National Park are 94°F, while nighttime lows are 61°F. Cap off your sightseeing on the 12th (Sun) early enough to go by car to 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.

On the 13th (Mon), stroll around Drake Park, relax and float downstream with a rafting and tubing tour, then contemplate the waterfront views at Deschutes River, and finally take a peaceful walk through Deschutes National Forest.

For more things to do, ratings, where to stay, and tourist information, refer to the Bend trip website.

You can drive from Crater Lake National Park to Bend in 2.5 hours. Alternatively, you can do a combination of taxi and bus. Plan for a bit cooler temperatures traveling from Crater Lake National Park in July, with highs in Bend at 85°F and lows at 52°F. Finish your sightseeing early on the 13th (Mon) so you can drive to Hood River.

The city of Hood River is the seat of Hood River County, Oregon, United States. Kick off your visit on the 14th (Tue): walk around Port Marina Park, then contemplate the waterfront views at Columbia River Gorge National Scenic Area, and then trek along Historic Columbia River Highway State Trail. Keep things going the next day: examine the collection at Western Antique Aeroplane & Automobile Museum, cruise along Hood River County Fruit Loop, and then tour the pleasant surroundings at Mount Hood.

Before you visit Hood River, use our trip planner to discover what you can do and see there.

Traveling by car from Bend to Hood River takes 3.5 hours. Alternatively, you can fly; or take a bus. While traveling from Bend, expect a bit cooler days and somewhat warmer nights in Hood River, ranging from highs of 79°F to lows of 58°F. Wrap up your sightseeing on the 15th (Wed) early enough to drive to Cannon Beach.

Cannon Beach is a city in Clatsop County, Oregon, United States. Kick off your visit on the 16th (Thu): kick back and relax at Cannon Beach, then view the masterpieces at Icefire Glassworks, then explore the striking landscape at Haystack Rock, and finally immerse yourself in nature at Hug Point State Park. Keep things going the next day: stop by Cloud and Leaf Bookstore, then kick back and relax at Manzanita Beach, then immerse yourself in nature at Oswald West State Park, and finally immerse yourself in nature at Ecola State Park.

For maps, where to stay, reviews, and other tourist information, you can read our Cannon Beach trip builder tool.

Drive from Hood River to Cannon Beach in 3 hours. Alternatively, you can take a bus; or do a combination of train and bus. Expect little chillier weather when traveling from Hood River in July: highs in Cannon Beach hover around 69°F, while lows dip to 55°F. Finish up your sightseeing early on the 17th (Fri) so you can go by car to 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 18th (Sat): stop by Powell's City of Books, take in nature's colorful creations at Lan Su Chinese Garden, admire the natural beauty at Portland Japanese Garden, then take in nature's colorful creations at International Rose Test Garden, and finally learn about wildlife with up-close encounters at Oregon Zoo. On the 19th (Sun), you'll have a packed day of sightseeing: learn the secrets of beer at a beer tour and tasting, admire the sheer force of Multnomah Falls, and then walk around Laurelhurst Park.

For other places to visit, reviews, ratings, and other tourist information, refer to the Portland trip planner.

Traveling by car from Cannon Beach to Portland takes 1.5 hours. Alternatively, you can take a bus. While traveling from Cannon Beach, expect a bit warmer days and about the same nights in Portland, ranging from highs of 83°F to lows of 59°F. You will leave for home on the 20th (Mon).