17 days in Oregon Itinerary

17 days in Oregon Itinerary

Created using Inspirock Oregon itinerary builder

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Route & dates

17 days in Oregon Itinerary

Start: Boston
Fly:  8​h 15​min
1
Portland
— 4 nights
Drive:  1​h 30​min
2
Cannon Beach
— 4 nights
Drive:  3​h
3
Hood River
— 4 nights
Drive:  3​h 15​min
4
Bend
— 3 nights
Fly:  11​h 30​min
End: Boston

4
nights
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.
Visit Pittock Mansion and Columbia River Highway for their historical value. For shopping fun, head to Powell's City of Books or Live Laugh Love Art. Venture out of the city with trips to Multnomah Falls (in Troutdale), Sokol Blosser Winery (in Dundee) and Evergreen Aviation & Space Museum (in McMinnville). The adventure continues: take in the dramatic scenery at Multnomah Falls, take an in-depth tour of Lake Oswego Preservation Society, admire the natural beauty at International Rose Test Garden, and wander the streets of Northwest (Nob Hill).

For reviews, maps, other places to visit, and other tourist information, read Portland trip itinerary maker .

Boston to Portland is an approximately 8.5-hour flight. You can also drive; or take a train. The time zone changes from Eastern Standard Time to Pacific Standard Time, which is usually a -3 hour difference. June in Portland sees daily highs of 77°F and lows of 56°F at night. Cap off your sightseeing on the 20th (Thu) early enough to go by car to Cannon Beach.

Things to do in Portland

Museums Parks Shopping

Side Trips

Lake Oswego, Evergreen Aviation & Space Museum, Camassia Natural Area, Sokol Blosser Winery, Multnomah Falls
Highlights from your plan
Powell's City of Books ©
Powell's City of Books
Multnomah Falls ©
Multnomah Falls
Evergreen Aviation & Space Museum ©
Evergreen Aviation & Space Museum

4
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. Get outdoors at Haystack Rock and Cannon Beach. Let the collections at Columbia River Maritime Museum and Rock Your World: Pacific Northwest Gem & Jewelry Gallery capture your imagination. Explore Cannon Beach's surroundings by going to Astoria (Astoria Column, Fort Clatsop National Memorial, & more), Lincoln City Glass Center (in Lincoln City) and Gleneden Beach State Park (in Gleneden Beach). Next up on the itinerary: immerse yourself in nature at Ecola State Park, don't miss a visit to Seaside Beach Lewis and Clark Monument, and see the interesting displays at Seaside Inverted Experience.

To see where to stay, traveler tips, more things to do, and tourist information, use the Cannon Beach travel itinerary planner .

Traveling by car from Portland to Cannon Beach takes 1.5 hours. Alternatively, you can take a bus. When traveling from Portland in June, plan for little chillier days and about the same nights in Cannon Beach: temperatures range from 66°F by day to 52°F at night. Wrap up your sightseeing on the 24th (Mon) to allow time to drive to Hood River.

Things to do in Cannon Beach

Parks Nature Historic Sites

Side Trips

Astoria, Lincoln City, Seaside, Gleneden Beach State Park
Highlights from your plan
Cannon Beach ©
Cannon Beach
Haystack Rock ©
Haystack Rock
Ecola State Park ©
Ecola State Park

4
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. Take a break from the city and head to Columbia River Gorge National Scenic Area and Mount Hood. Let the collections at Western Antique Aeroplane & Automobile Museum and Art on Oak capture your imagination. Explore Hood River's surroundings by going to Little Zigzag Falls (in Government Camp), Timberline Lodge and Ski Area (in Timberline Lodge) and Fire Museum in City Hall (in The Dalles). Next up on the itinerary: see the interesting displays at Columbia Gorge Discovery Center & Museum, immerse yourself in nature at Starvation Creek State Park, stroll around Port Marina Park, and trek along Historic Columbia River Highway State Trail.

For where to stay, traveler tips, more things to do, and more tourist information, go to the Hood River trip itinerary planner .

Drive from Cannon Beach to Hood River in 3 hours. Alternatively, you can take a bus; or do a combination of bus and train. Expect somewhat warmer weather when traveling from Cannon Beach in June: highs in Hood River hover around 72°F, while lows dip to 55°F. Cap off your sightseeing on the 28th (Fri) early enough to go by car to Bend.

Things to do in Hood River

Parks Nature Outdoors

Side Trips

The Dalles, Cascade Locks, Timberline Lodge and Ski Area, Historic Columbia River Highway State Trail, Little Zigzag Falls
Highlights from your plan

3
nights
Bend

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.
Give yourself a bit of retail therapy at Artists Gallery Sunriver and Old Mill District. Museum-lovers will get to explore High Desert Museum and Oregon Observatory. Step out of Bend to go to Redmond and see Smith Rock State Park, which is approximately 38 minutes away. The adventure continues: explore the striking landscape of Deschutes National Forest, trek along Shevlin Park, relax and float downstream with a rafting and tubing tour, and take in the dramatic natural features at Balancing Rocks.

For maps, where to stay, ratings, and other tourist information, you can read our Bend holiday builder website .

Traveling by car from Hood River to Bend takes 3.5 hours. Alternatively, you can do a combination of bus and flight; or take a bus. Expect slightly colder evenings in Bend when traveling from Hood River in June, with lows around 45°F. Wrap up your sightseeing on the 1st (Mon) to allow time to travel back home.

Things to do in Bend

Parks Nature Museums

Side Trips

Sunriver, Smith Rock State Park
Highlights from your plan
High Desert Museum ©
High Desert Museum
Smith Rock State Park ©
Smith Rock State Park
River Rafting & Tubing

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