14 days in Oregon Itinerary

14 days in Oregon Itinerary

Created using Inspirock Oregon trip planner

Make it your trip
Fly
1
Bend
— 1 night
Fly
2
Hood River
— 2 nights
Drive
3
Portland
— 3 nights
Drive
4
Newport
— 3 nights
Drive
5
Cannon Beach
— 2 nights
Fly
6
Crater Lake National Park
— 1 night
Drive
7
Ashland
— 1 night
Fly

S M T W T F S
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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.
On the 11th (Sat), see the interesting displays at High Desert Museum and then relax and float downstream with a rafting and tubing tour. Get ready for a full day of sightseeing on the 12th (Sun): look and learn at Oregon Observatory and then take a memorable drive along McKenzie Pass-Santiam Pass loop.

To find photos, where to stay, maps, and tourist information, you can read our Bend trip planner.

El Paso to Bend is an approximately 6.5-hour flight. You can also drive; or take a bus. You'll gain 1 hour traveling from El Paso to Bend due to the time zone difference. Expect much colder temperatures when traveling from El Paso in June; daily highs in Bend reach 75°F and lows reach 45°F. Wrap up your sightseeing on the 12th (Sun) to allow time to fly to Hood River.

Things to do in Bend

Outdoors · Museums · Adventure · Childrens Museums

Side Trips

Find places to stay Jun 11 — 12:
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Hood River

— 2 nights
The city of Hood River is the seat of Hood River County, Oregon, United States. Start off your visit on the 13th (Mon): see human ingenuity at work at Bonneville Lock & Dam and then stroll through Mount Hood. Get ready for a full day of sightseeing on the 14th (Tue): see the interesting displays at Western Antique Aeroplane & Automobile Museum and then explore the activities along Columbia River Gorge National Scenic Area.

For photos, where to stay, reviews, and more tourist information, you can read our Hood River itinerary website.

Traveling by flight from Bend to Hood River takes 2.5 hours. Alternatively, you can drive; or take a bus. Traveling from Bend in June, expect a bit warmer with lows of 55°F in Hood River. Wrap up your sightseeing on the 14th (Tue) early enough to drive to Portland.

Things to do in Hood River

Parks · Nature · Outdoors · Winter Sports

Side Trips

Find places to stay Jun 12 — 14:
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Portland

— 3 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.
Kids will enjoy International Rose Test Garden and Powell's City of Books. Go for a jaunt from Portland to Bridal Veil to see Multnomah Falls about 38 minutes away. There's much more to do: admire the natural beauty at Portland Japanese Garden, meet the residents at Washington Park, trek along Forest Park, and admire the landmark architecture of Pittock Mansion.

For maps, ratings, more things to do, and other tourist information, refer to the Portland travel route planner.

You can drive from Hood River to Portland in 1.5 hours. Other options are to take a bus; or take a train. In June, plan for daily highs up to 77°F, and evening lows to 56°F. Cap off your sightseeing on the 17th (Fri) early enough to go by car to Newport.

Things to do in Portland

Parks · Zoos & Aquariums · Nature · Trails

Side Trip

Find places to stay Jun 14 — 17:
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Newport

— 3 nights
A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
Kids will appreciate attractions like Oregon Coast Aquarium and Marine Discovery Tours. Venture out of the city with trips to Beachtown Charities Thrift and Gift (in Lincoln City) and Yachats (Cape Perpetua Visitor Center - Siuslaw National Forest & Yachats coastline). There's much more to do: tour the pleasant surroundings at Yaquina Head Outstanding Natural Area, visit a coastal fixture at Yaquina Head Lighthouse, and trek along Devils Punchbowl State Natural Area.

For ratings, reviews, maps, and more tourist information, read our Newport online travel route planner.

Getting from Portland to Newport by car takes about 2.5 hours. Other options: take a bus; or do a combination of train and bus. In June, Newport is slightly colder than Portland - with highs of 61°F and lows of 48°F. Wrap up your sightseeing on the 20th (Mon) to allow time to drive to Cannon Beach.

Things to do in Newport

Parks · Outdoors · Nature · Wildlife

Side Trips

Find places to stay Jun 17 — 20:
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Cannon Beach

— 2 nights
Cannon Beach is a city in Clatsop County, Oregon, United States. On the 21st (Tue), enjoy the sand and surf at Cannon Beach, then take in the dramatic natural features at Haystack Rock, and then take in the exciting artwork at Icefire Glassworks. Get ready for a full day of sightseeing on the next day: admire the majestic nature at Ecola State Park and then admire the majestic nature at Oswald West State Park.

To find reviews, other places to visit, where to stay, and more tourist information, go to the Cannon Beach attractions planning website.

Getting from Newport to Cannon Beach by car takes about 3 hours. Other options: take a bus. June in Cannon Beach sees daily highs of 66°F and lows of 52°F at night. Finish up your sightseeing early on the 22nd (Wed) so you can catch the flight to Crater Lake National Park.

Things to do in Cannon Beach

Parks · Nature · Outdoors · Beaches
Find places to stay Jun 20 — 22:
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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.
Kick off your visit on the 23rd (Thu): explore the striking landscape of Crater Lake National Park.

For traveler tips, where to stay, photos, and more tourist information, use the Crater Lake National Park trip site.

Getting from Cannon Beach to Crater Lake National Park by flight takes about 2.5 hours. Other options: drive; or do a combination of bus and taxi. Traveling from Cannon Beach in June, you will find days in Crater Lake National Park are somewhat warmer (86°F), and nights are about the same (55°F). Finish your sightseeing early on the 23rd (Thu) so you can drive to Ashland.

Things to do in Crater Lake National Park

Nature · Parks
Find places to stay Jun 22 — 23:
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Highlights from your trip

Ashland

— 1 night
Ashland is a city in Jackson County, in the State of Oregon. On the 24th (Fri), see a show at Oregon Shakespeare Festival and then get a new perspective on things with Boat Tours & Water Sports.

To find maps, photos, reviews, and tourist information, you can read our Ashland trip itinerary maker site.

Traveling by car from Crater Lake National Park to Ashland takes 2 hours. Alternatively, you can do a combination of taxi and bus. In June, daily temperatures in Ashland can reach 86°F, while at night they dip to 55°F. Finish your sightseeing early on the 24th (Fri) to allow enough time to fly back home.

Things to do in Ashland

Nightlife · Adventure · Outdoors · Tours
Find places to stay Jun 23 — 24:
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Oregon travel guide

4.5
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.