14 days in Oregon Itinerary

14 days in Oregon Itinerary

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

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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 1st (Wed), examine the collection at High Desert Museum and then head outdoors with Outdoor Activities. On the next day, take a memorable drive along McKenzie Pass-Santiam Pass loop and then admire the majestic nature at Smith Rock State Park.

To see traveler tips, reviews, where to stay, and tourist information, read our Bend online itinerary planner.

Newark to Bend is an approximately 8.5-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 Newark to Bend. Prepare for little chillier weather when traveling from Newark in June: high temperatures in Bend hover around 75°F and lows are around 45°F. Wrap up your sightseeing on the 2nd (Thu) to allow time to drive to Crater Lake National Park.
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Outdoors · Museums · Adventure · Nature
Side Trips

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.
Start off your visit on the 3rd (Fri): explore the striking landscape of Crater Lake National Park.

To find traveler tips, more things to do, reviews, and more tourist information, read our Crater Lake National Park online trip maker.

Traveling by car from Bend to Crater Lake National Park takes 2.5 hours. Alternatively, you can do a combination of bus and taxi. Plan for a bit warmer temperatures traveling from Bend in June, with highs in Crater Lake National Park at 86°F and lows at 55°F. Finish up your sightseeing early on the 3rd (Fri) so you can go by car to Ashland.
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Nature · Parks
Highlights from your trip

Ashland — 1 night

Ashland is a city in Jackson County, in the State of Oregon. On the 4th (Sat), let the river carry you with a rafting and tubing tour, do a tasting at Grizzly Peak Winery, and then walk around Lithia Park.

To see photos, ratings, and tourist information, go to the Ashland trip website.

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 4th (Sat) so you can drive to Newport.
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Adventure · Outdoors · Parks · Tours

Newport — 2 nights

A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
On the 5th (Sun), get up close to creatures of the deep with Marine Discovery Tours, observe the fascinating underwater world at Oregon Coast Aquarium, and then take a leisurely stroll along Yachats coastline. Get ready for a full day of sightseeing on the 6th (Mon): take a memorable drive along Cape Perpetua Visitor Center - Siuslaw National Forest and then stroll through Yaquina Head Outstanding Natural Area.

To find where to stay, traveler tips, and tourist information, go to the Newport trip maker tool.

You can drive from Ashland to Newport in 5 hours. Other options are to do a combination of flight and bus; or take a bus. Traveling from Ashland in June, you will find days in Newport are much colder (61°F), and nights are a bit cooler (48°F). Wrap up your sightseeing on the 6th (Mon) early enough to drive to Astoria.
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Parks · Wildlife · Outdoors · Nature
Side Trip

Astoria — 3 nights

Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
Explore Astoria's surroundings by going to Cannon Beach (Icefire Glassworks, Haystack Rock, &more). There's lots more to do: appreciate the history behind Astoria Column, contemplate the waterfront views at Columbia River Maritime Museum, and immerse yourself in nature at Fort Stevens State Park.

To see where to stay, more things to do, and other tourist information, read our Astoria trip itinerary site.

Getting from Newport to Astoria by car takes about 3.5 hours. Other options: take a bus. Expect a daytime high around 66°F in June, and nighttime lows around 52°F. Finish your sightseeing early on the 9th (Thu) to allow enough time to drive to Portland.
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Parks · Nature · Beaches · Outdoors
Side Trip

Portland — 3 nights

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.
Take a break from Portland with a short trip to Multnomah Falls in Bridal Veil, about 38 minutes away. There's much more to do: admire the natural beauty at International Rose Test Garden, walk around Peninsula Park and Rose Gardens, admire the striking features of Pittock Mansion, and examine the collection at Oregon Museum of Science and Industry.

To see where to stay, more things to do, photos, and tourist information, go to the Portland online trip itinerary builder.

Traveling by car from Astoria to Portland takes 2 hours. Alternatively, you can take a bus. Expect somewhat warmer weather when traveling from Astoria in June: highs in Portland hover around 77°F, while lows dip to 56°F. Finish your sightseeing early on the 12th (Sun) so you can drive to Hood River.
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Parks · Breweries & Distilleries · Tours · Nature
Side Trip

Hood River — 2 nights

The city of Hood River is the seat of Hood River County, Oregon, United States. Kick off your visit on the 13th (Mon): see the interesting displays at Western Antique Aeroplane & Automobile Museum and then contemplate the waterfront views at Columbia River Gorge National Scenic Area. Get ready for a full day of sightseeing on the 14th (Tue): take a memorable drive along Hood River County Fruit Loop.

For more things to do, maps, photos, and more tourist information, go to the Hood River vacation planning app.

You can drive from Portland to Hood River in 1.5 hours. Other options are to take a bus; or take a train. Traveling from Portland in June, expect nights in Hood River to be about the same, around 55°F, while days are a bit cooler, around 72°F. On the 14th (Tue), wrap the sightseeing up by early afternoon so you can fly back home.
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Museums · Wildlife · Nature · Scenic Drive
Side Trip

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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