18 days in Oregon Itinerary

18 days in Oregon Itinerary

Created using Inspirock Oregon trip planner

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

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Ashland

— 1 night
Ashland is a city in Jackson County, in the State of Oregon. On the 1st (Wed), catch a live performance at Oregon Shakespeare Festival. On the 2nd (Thu), you'll have a packed day of sightseeing: view the masterpieces at The Glass Forge, learn about winemaking at Grizzly Peak Winery, and then stroll around Lithia Park.

For reviews, traveler tips, more things to do, and tourist information, read our Ashland trip itinerary builder tool.

Cleveland to Ashland is an approximately 8.5-hour flight. You can also drive; or do a combination of train and bus. The time zone difference when traveling from Cleveland to Ashland is minus 3 hours. Expect somewhat warmer weather when traveling from Cleveland in June: highs in Ashland hover around 86°F, while lows dip to 55°F. Wrap up your sightseeing on the 2nd (Thu) early enough to drive to Crater Lake National Park.

Things to do in Ashland

Nightlife · Museums · Parks · Shopping

Side Trip

Find places to stay Jun 1 — 2:

Crater Lake National Park

— 2 nights
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 3rd (Fri): explore the striking landscape of Crater Lake National Park. On the 4th (Sat), you'll have a packed day of sightseeing: tour the pleasant surroundings at Rogue River Gorge Viewpoint and then admire all the interesting features of Rim Dr.

To see maps, where to stay, photos, and other tourist information, use the Crater Lake National Park trip itinerary tool.

You can drive from Ashland to Crater Lake National Park in 2 hours. Alternatively, you can do a combination of bus and taxi. Expect a daytime high around 86°F in June, and nighttime lows around 55°F. Wrap up your sightseeing on the 4th (Sat) to allow time to drive to Bend.

Things to do in Crater Lake National Park

Parks · Nature · Outdoors · Scenic Drive

Side Trip

Find places to stay Jun 2 — 4:

Bend

— 3 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.
Get out of town with these interesting Bend side-trips: Sisters (Sahalie and Koosah Falls & McKenzie Pass-Santiam Pass loop) and Smith Rock State Park (in Redmond). And it doesn't end there: examine the collection at High Desert Museum, trek along Falls Creek Trail to Green Lake, and explore the wealth of natural beauty at Deschutes National Forest.

For other places to visit, ratings, where to stay, and more tourist information, read our Bend holiday planning tool.

Traveling by car from Crater Lake National Park to Bend takes 2.5 hours. Alternatively, you can do a combination of taxi and bus. Traveling from Crater Lake National Park in June, expect Bend to be little chillier, temps between 75°F and 45°F. Wrap up your sightseeing on the 7th (Tue) to allow time to drive to Newport.

Things to do in Bend

Parks · Nature · Outdoors · Trails

Side Trips

Find places to stay Jun 4 — 7:

Newport

— 2 nights
A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
Kick off your visit on the 8th (Wed): get up close and personal with brilliant marine life at Oregon Coast Aquarium, then look for all kinds of wild species at Marine Discovery Tours, and then tour the pleasant surroundings at Yaquina Head Outstanding Natural Area. On your second day here, cruise along Cape Perpetua Visitor Center - Siuslaw National Forest and then take in the waterfront at Yachats coastline.

To find photos, traveler tips, where to stay, and tourist information, read Newport day trip website.

You can drive from Bend to Newport in 4.5 hours. Other options are to do a combination of flight and bus; or take a bus. Traveling from Bend in June, expect nights in Newport to be about the same, around 48°F, while days are little chillier, around 61°F. Wrap up your sightseeing on the 9th (Thu) to allow time to drive to Astoria.

Things to do in Newport

Parks · Outdoors · Wildlife · Nature

Side Trip

Find places to stay Jun 7 — 9:

Astoria

— 3 nights

Spirit of the Columbia

Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
Get out of town with these interesting Astoria side-trips: Cannon Beach (Cannon Beach, Oswald West State Park, &more). And it doesn't end there: tour the pleasant surroundings at Astoria Column, contemplate the waterfront views at Columbia River Maritime Museum, and admire the majestic nature at Fort Stevens State Park.

To see traveler tips, ratings, more things to do, and tourist information, go to the Astoria route builder app.

You can drive from Newport to Astoria in 3.5 hours. Another option is to take a bus. In June, daily temperatures in Astoria can reach 66°F, while at night they dip to 52°F. Wrap up your sightseeing on the 12th (Sun) early enough to drive to Portland.

Things to do in Astoria

Parks · Nature · Outdoors · Beaches

Side Trip

Find places to stay Jun 9 — 12:

Portland

— 4 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.
Venture out of the city with trips to Evergreen Aviation & Space Museum (in McMinnville), Multnomah Falls (in Bridal Veil) and Cellar Door Wine Tours (in Lafayette). The adventure continues: admire the natural beauty at International Rose Test Garden, examine the collection at Oregon Museum of Science and Industry, admire nature's wide array of creatures at Oregon Zoo, and make a trip to Pittock Mansion.

To see more things to do, maps, photos, and tourist information, refer to the Portland trip builder app.

Traveling by car from Astoria to Portland takes 2 hours. Alternatively, you can take a bus. When traveling from Astoria in June, plan for a bit warmer days in Portland, with highs around 77°F, while nights are about the same with lows around 56°F. Finish your sightseeing early on the 16th (Thu) to allow enough time to drive to Hood River.

Things to do in Portland

Parks · Tours · Museums · Wineries

Side Trips

Find places to stay Jun 12 — 16:

Hood River

— 2 nights
The city of Hood River is the seat of Hood River County, Oregon, United States. On the 17th (Fri), examine the collection at Western Antique Aeroplane & Automobile Museum and then explore the activities along Columbia River Gorge National Scenic Area.

To see photos, where to stay, other places to visit, and more tourist information, use the Hood River travel route planner.

You can drive from Portland to Hood River in 1.5 hours. Other options are to take a bus; or take a train. When traveling from Portland in June, plan for slightly colder days in Hood River, with highs around 72°F, while nights are about the same with lows around 55°F. On the 18th (Sat), you're off to home.

Things to do in Hood River

Nature · Museums · Parks · Wildlife

Side Trip

Find places to stay Jun 16 — 18:

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.