26 days in Oregon Itinerary

Cannon Beach is a city in Clatsop County, Oregon, United States. Get out of town with these interesting Cannon Beach side-trips: Rockaway Beach (International Police Museum & Cedar Wetlands Preserve), Netarts Bay (in Netarts) and Tillamook Air Museum (in Tillamook). And it doesn't end there: enjoy the sand and surf at Haystack Rock, explore and take pictures at Three Capes Scenic Drive, immerse yourself in nature at Hug Point State Park, and take your sightseeing to a higher altitude at Neahkahnie Mountain.

To find maps, other places to visit, and tourist information, read Cannon Beach trip maker tool.

Toronto, Canada to Cannon Beach is an approximately 8.5-hour flight. You can also drive; or do a combination of train, car, and bus. You'll gain 3 hours traveling from Toronto to Cannon Beach due to the time zone difference. Traveling from Toronto in September, Cannon Beach is little chillier at night with lows of 13°C. Wrap up your sightseeing on the 7th (Thu) to allow time to drive to Newport.

A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.

Venture out of the city with trips to Yachats (Cape Perpetua Visitor Center - Siuslaw National Forest & Yachats coastline), Lincoln City Glass Center (in Lincoln City) and Heceta Head Lighthouse (in Florence). And it doesn't end there: admire nature's wide array of creatures at Oregon Coast Aquarium, enjoy the sand and surf at Nye Beach, walk around Whale Park, and enjoy the sea views from Yaquina Head Lighthouse.

To see traveler tips, more things to do, other places to visit, and tourist information, read Newport trip itinerary planning site.

Drive from Cannon Beach to Newport in 3 hours. Alternatively, you can take a bus. Traveling from Cannon Beach in September, expect nights in Newport to be about the same, around 11°C, while days are a bit cooler, around 20°C. Cap off your sightseeing on the 11th (Mon) early enough to 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.

Venture out of the city with trips to Multnomah Falls (in Bridal Veil) and Evergreen Aviation & Space Museum (in McMinnville). Dedicate the 14th (Thu) to wine at some of the top wineries in the area. There's still lots to do: take in nature's colorful creations at Portland Japanese Garden, walk around Tom McCall Waterfront Park, get to know the resident critters at Oregon Zoo, and don't miss a visit to Pittock Mansion.

To find where to stay, other places to visit, more things to do, and more tourist information, read Portland travel route planner.

Traveling by car from Newport to Portland takes 2.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. Expect a bit warmer weather when traveling from Newport in September: highs in Portland hover around 28°C, while lows dip to 15°C. Finish your sightseeing early on the 16th (Sat) so you can drive to Hood River.

The city of Hood River is the seat of Hood River County, Oregon, United States. Explore Hood River's surroundings by going to Government Camp (Timberline Lodge and Ski Area, Trillium Lake, &more) and Bonneville Lock & Dam (in Cascade Locks). The adventure continues: contemplate the waterfront views at Columbia River Gorge National Scenic Area, see the interesting displays at Columbia Gorge Discovery Center & Museum, immerse yourself in nature at Starvation Creek State Park, and get engrossed in the history at Fort Dalles Museum and Anderson Homestead.

To find traveler tips, other places to visit, ratings, and other tourist information, use the Hood River online day trip planner.

You can drive from Portland to Hood River in 1.5 hours. Alternatively, you can take a bus; or take a train. When traveling from Portland in September, plan for slightly colder days in Hood River, with highs around 25°C, while nights are about the same with lows around 16°C. Finish your sightseeing early on the 20th (Wed) to allow enough time to fly to Crater Lake National Park.

Reaching a depth of 592 m (1,943 ft), Crater Lake is the deepest lake in the United States.

Take a break from Crater Lake National Park with a short trip to Natural Bridge Viewpoint in Prospect, about 44 minutes away. Spend the 22nd (Fri) exploring nature at Crater Lake National Park. There's much more to do: explore and take pictures at Rim Dr, take a memorable drive along Rogue-Umpqua Scenic Byway, stroll through Pinnacles Overlook Hike, and admire the sheer force of Whitehorse Falls.

Plan a Crater Lake National Park trip in moments using our itinerary builder.

You can fly from Hood River to Crater Lake National Park in 2.5 hours. Alternatively, you can drive; or do a combination of bus and taxi. When traveling from Hood River in September, plan for somewhat warmer days in Crater Lake National Park, with highs around 33°C, while nights are about the same with lows around 13°C. Finish your sightseeing early on the 23rd (Sat) so you can drive 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.

Get out of town with these interesting Bend side-trips: Dee Wright Observatory (in Blue River), Wildland Firefighters Monument (in Prineville) and Sisters (Sahalie and Koosah Falls & McKenzie Pass-Santiam Pass loop). There's much more to do: immerse yourself in nature at Smith Rock State Park, let the river carry you with a rafting and tubing tour, admire the sheer force of Tumalo Falls, and stroll around Drake Park.

Find out how to plan Bend trip without stress by asking Inspirock to help create an itinerary.

Traveling by car from Crater Lake National Park to Bend takes 2.5 hours. Alternatively, you can do a combination of taxi and bus. Expect slightly colder temperatures when traveling from Crater Lake National Park in September; daily highs in Bend reach 26°C and lows reach 7°C. On the 29th (Fri), you'll travel back home.