31 days in Oregon Itinerary

31 days in Oregon Itinerary

Created using Inspirock Oregon route planner
Make it your trip
Fly
1
Cannon Beach
— 3 nights
Drive
2
Newport
— 4 nights
Drive
3
Portland
— 6 nights
Drive
4
Hood River
— 4 nights
Fly
5
Ashland
— 3 nights
Drive
6
Crater Lake National Park
— 3 nights
Drive
7
Bend
— 6 nights
Fly

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Cannon Beach — 3 nights

Cannon Beach is a city in Clatsop County, Oregon, United States. Get out of town with these interesting Cannon Beach side-trips: Tillamook Air Museum (in Tillamook), Cedar Wetlands Preserve (in Rockaway Beach) and Netarts Bay (in Netarts). And it doesn't end there: take in the dramatic natural features at Haystack Rock, stroll through Cannon Beach, immerse yourself in nature at Oswald West State Park, and kick back and relax at Manzanita Beach.

To see traveler tips, where to stay, maps, and tourist information, you can read our Cannon Beach day trip site.

Sydney, Australia to Cannon Beach is an approximately 20.5-hour flight. Traveling from Sydney to Cannon Beach, you'll gain 18 hours due to the time zone difference. Traveling from Sydney in October, expect Cannon Beach to be a bit cooler, temps between 20°C and 10°C. Wrap up your sightseeing on the 4th (Wed) to allow time to drive to Newport.
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Parks · Outdoors · Nature · Beaches
Side Trips

Newport — 4 nights

A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
You'll find plenty of places to visit near Newport: Yachats (Cape Perpetua Visitor Center - Siuslaw National Forest & Yachats coastline) and Florence (Sea Lion Caves & Heceta Head Lighthouse). There's much more to do: get up close and personal with brilliant marine life at Oregon Coast Aquarium, stroll around Whale Park, kick back and relax at Nye Beach, and take a memorable drive along Oregon Coast Hwy.

To find ratings, maps, more things to do, and more tourist information, refer to the Newport trip itinerary planner.

Traveling by car from Cannon Beach to Newport takes 3 hours. Alternatively, you can take a bus. In October, daily temperatures in Newport can reach 18°C, while at night they dip to 10°C. Finish your sightseeing early on the 8th (Sun) to allow enough time to drive to Portland.
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Parks · Outdoors · Scenic Drive · Nature
Side Trips

Portland — 6 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.
You'll find plenty of places to visit near Portland: Oneonta Gorge (in Cascade Locks), Cellar Door Wine Tours (in Lafayette) and Multnomah Falls (in Bridal Veil). Next up on the itinerary: admire the natural beauty at Portland Japanese Garden, admire the striking features of Pittock Mansion, learn about wildlife with up-close encounters at Oregon Zoo, and see the interesting displays at Evergreen Aviation & Space Museum.

For ratings, other places to visit, where to stay, and tourist information, refer to the Portland day trip planning website.

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. While traveling from Newport, expect somewhat warmer days and about the same nights in Portland, ranging from highs of 22°C to lows of 11°C. Cap off your sightseeing on the 14th (Sat) early enough to go by car to Hood River.
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Parks · Tours · Wineries · Museums
Side Trips

Hood River — 4 nights

The city of Hood River is the seat of Hood River County, Oregon, United States. Explore Hood River's surroundings by going to Bonneville Lock & Dam (in Cascade Locks), Timberline Lodge and Ski Area (in Timberline Lodge) and Government Camp (Trillium Lake & Little Zigzag Falls). The adventure continues: explore the activities along Columbia River Gorge National Scenic Area, sample the fine beverages at Hood River Distillers Tasting Room, see the interesting displays at Fire Museum in City Hall, and take a peaceful walk through Mt. Hood National Forest.

To see more things to do, reviews, maps, and tourist information, use the Hood River trip planner.

Traveling by car from Portland to Hood River takes 1.5 hours. Alternatively, you can take a bus; or take a train. October in Hood River sees daily highs of 22°C and lows of 8°C at night. Finish your sightseeing early on the 18th (Wed) so you can fly to Ashland.
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Parks · Nature · Outdoors · Museums
Side Trips

Ashland — 3 nights

Ashland is a city in Jackson County, in the State of Oregon. Venture out of the city with trips to Wildlife Images - Rehabilitation & Education Center (in Grants Pass), Medford (Rogue River & Natural Bridge Loop) and Pacific Crest National Scenic Trail (in Dufur). The adventure continues: get a new perspective on things with Boat Tours & Water Sports, awaken your taste buds at Main Street Adventure Tours, walk around Lithia Park, and catch a live performance at Oregon Shakespeare Festival.

To find maps, more things to do, other places to visit, and tourist information, use the Ashland online visit planner.

Getting from Hood River to Ashland by flight takes about 2.5 hours. Other options: drive; or take a bus. In October, plan for daily highs up to 25°C, and evening lows to 7°C. Finish up your sightseeing early on the 21st (Sat) so you can go by car to Crater Lake National Park.
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Outdoors · Parks · Tours · Wildlife
Side Trips

Crater Lake National Park — 3 nights

Reaching a depth of 592 m (1,943 ft), Crater Lake is the deepest lake in the United States.
Step out of Crater Lake National Park with an excursion to National Creek Falls in Prospect--about 30 minutes away. Spend the 22nd (Sun) exploring nature at Crater Lake National Park. There's much more to do: take a memorable drive along Rim Dr, tour the pleasant surroundings at Pinnacles Overlook Hike, admire all the interesting features of Rogue-Umpqua Scenic Byway, and step off the mainland to explore Wizard Island.

For where to stay, other places to visit, maps, and other tourist information, read Crater Lake National Park online trip builder.

You can drive from Ashland to Crater Lake National Park in 2 hours. Another option is to do a combination of bus and taxi. October in Crater Lake National Park sees daily highs of 25°C and lows of 7°C at night. Wrap up your sightseeing on the 24th (Tue) to allow time to drive to Bend.
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Parks · Nature · Outdoors · Scenic Drive
Side Trips

Bend — 6 nights

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.
Explore Bend's surroundings by going to Sisters (Sahalie and Koosah Falls, Proxy Falls, &more), Dee Wright Observatory (in Blue River) and Prineville (Steins Pillar & Wildland Firefighters Monument). There's lots more to do: admire the majestic nature at Smith Rock State Park, hike along Pilot Butte State Scenic Viewpoint, delve into the lush surroundings at Deschutes National Forest, and relax and float downstream with a rafting and tubing tour.

To find where to stay, photos, other places to visit, and more tourist information, you can read our Bend trip itinerary maker app.

You can drive from Crater Lake National Park to Bend in 2.5 hours. Alternatively, you can do a combination of taxi and bus. In October, Bend is a bit cooler than Crater Lake National Park - with highs of 19°C and lows of 3°C. Wrap up your sightseeing on the 30th (Mon) to allow time to fly back home.
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Parks · Nature · Outdoors · Museums
Side Trips

Oregon travel guide

4.5
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.
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