23 days in Oregon Itinerary

23 days in Oregon Itinerary

Created using Inspirock Oregon trip itinerary planner
Make it your trip
Fly
1
Portland
— 5 nights
Drive
2
Hood River
— 3 nights
Fly
3
Bend
— 3 nights
Drive
4
Crater Lake National Park
— 1 night
Drive
5
Ashland
— 3 nights
Drive
6
Newport
— 3 nights
Drive
7
Astoria
— 3 nights
Drive to Seattle Tacoma International Airport, Fly to Oslo

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Portland — 5 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.
Explore the numerous day-trip ideas around Portland: Multnomah Falls (in Bridal Veil) and Salem (Schreiner's Iris Gardens & Adelman Peony Gardens). Dedicate the 29th (Sun) to wine at some of the top wineries in the area. Next up on the itinerary: take in nature's colorful creations at Portland Japanese Garden, sample some tasty brews at a beer tour and tasting, surround yourself with nature on Volcano Lands - Private Tours, and get to know the resident critters at Oregon Zoo.

To find where to stay, photos, maps, and more tourist information, you can read our Portland trip itinerary maker tool.

Oslo, Norway to Portland is an approximately 16.5-hour flight. Traveling from Oslo to Portland, you'll gain 9 hours due to the time zone difference. Traveling from Oslo in May, expect Portland to be a bit warmer, temps between 24°C and 12°C. Finish your sightseeing early on the 1st (Wed) to allow enough time to drive to Hood River.
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Parks · Tours · Wineries · Wildlife
Side Trips

Hood River — 3 nights

The city of Hood River is the seat of Hood River County, Oregon, United States. You'll find plenty of places to visit near Hood River: Timberline Lodge and Ski Area (in Timberline Lodge) and Bonneville Lock & Dam (in Cascade Locks). And it doesn't end there: explore the activities along Columbia River Gorge National Scenic Area, hike along Historic Columbia River Highway State Trail, contemplate the geological forces at Mount Hood, and examine the collection at Columbia Gorge Discovery Center & Museum.

To find traveler tips, ratings, and other tourist information, read Hood River tour itinerary planner.

Getting from Portland to Hood River by car takes about 1.5 hours. Other options: take a bus; or take a train. Traveling from Portland in June, you will find days in Hood River are a bit cooler (26°C), and nights are about the same (15°C). Wrap up your sightseeing on the 4th (Sat) early enough to fly to Bend.
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Parks · Nature · Outdoors · Winter Sports
Side Trips

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.
Explore the numerous day-trip ideas around Bend: Sisters (Sahalie and Koosah Falls & McKenzie Pass-Santiam Pass loop) and Smith Rock State Park (in Redmond). There's lots more to do: examine the collection at High Desert Museum, see Off-Road Tours, let the river carry you with a rafting and tubing tour, and hike along Falls Creek Trail to Green Lake.

To see reviews, where to stay, ratings, and tourist information, read Bend journey planner.

You can fly from Hood River to Bend in 2.5 hours. Alternatively, you can drive; or take a bus. Traveling from Hood River in June, you can expect nighttime temperatures to be slightly colder in Bend, with lows of 8°C. Wrap up your sightseeing on the 7th (Tue) to allow time to drive to Crater Lake National Park.
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Outdoors · Parks · Nature · Tours
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.
Kick off your visit on the 8th (Wed): explore the striking landscape of Crater Lake National Park.

To find other places to visit, photos, traveler tips, and other tourist information, read Crater Lake National Park online vacation planner.

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 somewhat warmer temperatures traveling from Bend in June, with highs in Crater Lake National Park at 35°C and lows at 15°C. Finish up your sightseeing early on the 8th (Wed) so you can go by car to Ashland.
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Nature · Parks
Highlights from your trip

Ashland — 3 nights

Ashland is a city in Jackson County, in the State of Oregon. Explore the numerous day-trip ideas around Ashland: Grants Pass (Wildlife Images - Rehabilitation & Education Center & The Glass Forge) and Medford (Upper and Lower Table Rock & Rogue River). The adventure continues: stroll around Lithia Park, head outdoors with Outdoor Activities, and learn about winemaking at Grizzly Peak Winery.

To see other places to visit, traveler tips, maps, and other tourist information, use the Ashland travel planning app.

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, daytime highs in Ashland are 35°C, while nighttime lows are 15°C. Wrap up your sightseeing on the 11th (Sat) early enough to drive to Newport.
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Parks · Nature · Outdoors · Adventure
Side Trips

Newport — 3 nights

A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
Get out of town with these interesting Newport side-trips: Yachats (Cape Perpetua Visitor Center - Siuslaw National Forest & Yachats coastline) and Lincoln City (Beachtown Charities Thrift and Gift & Lincoln City Glass Center). The adventure continues: meet the residents at Oregon Coast Aquarium, tour the pleasant surroundings at Yaquina Head Outstanding Natural Area, and take in the waterfront at Newport's Historic Bayfront.

Plan my trip to Newport with suggested itineraries provided by Inspirock.

Traveling by car from Ashland to Newport takes 5 hours. Alternatively, you can do a combination of flight and bus; or take a bus. Expect much colder weather when traveling from Ashland in June: highs in Newport hover around 19°C, while lows dip to 10°C. Finish your sightseeing early on the 14th (Tue) to allow enough time to drive to Astoria.
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Parks · Shopping · Nature · Outdoors
Side Trips

Astoria — 3 nights

Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
You'll find plenty of places to visit near Astoria: Cannon Beach (Haystack Rock, Ecola State Park, &more). There's still lots to do: learn and have fun at Columbia River Maritime Museum, admire the majestic nature at Fort Stevens State Park, and appreciate the history behind Astoria Column.

To find where to stay, traveler tips, reviews, and tourist information, use the Astoria holiday app.

You can drive from Newport to Astoria in 3.5 hours. Another option is to take a bus. In June, plan for daily highs up to 22°C, and evening lows to 13°C. Wrap up your sightseeing on the 17th (Fri) to allow time to travel back home.
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Parks · Nature · Outdoors · Beaches
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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