19 days in Oregon Itinerary

19 days in Oregon Itinerary

Created using Inspirock Oregon itinerary builder

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

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Astoria

— 2 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 (Icefire Glassworks, Haystack Rock, &more). The adventure continues: appreciate the history behind Astoria Column, explore the activities along Columbia River Maritime Museum, and admire the majestic nature at Fort Stevens State Park.

To find other places to visit, reviews, and more tourist information, read our Astoria route builder tool.

Portland to Astoria is an approximately 2-hour car ride. You can also take a bus. When traveling from Portland in June, plan for a bit cooler days and about the same nights in Astoria: temperatures range from 66°F by day to 52°F at night. Cap off your sightseeing on the 8th (Wed) early enough to go by car to Newport.

Things to do in Astoria

Parks · Nature · Beaches · Outdoors

Side Trip

Find places to stay Jun 6 — 8:

Newport

— 3 nights
A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
You'll find plenty of places to visit near Newport: Yachats (Yachats coastline & Cape Perpetua Visitor Center - Siuslaw National Forest), Beachtown Charities Thrift and Gift (in Lincoln City) and Heceta Head Lighthouse (in Florence). There's still lots to do: tour the pleasant surroundings at Yaquina Head Outstanding Natural Area, take a tour by water with Marine Discovery Tours, observe the fascinating underwater world at Oregon Coast Aquarium, and enjoy the sea views from Yaquina Head Lighthouse.

To find more things to do, ratings, maps, and tourist information, read our Newport tour builder tool.

You can drive from Astoria to Newport in 3.5 hours. Another option is to take a bus. When traveling from Astoria in June, plan for little chillier days in Newport, with highs around 61°F, while nights are about the same with lows around 48°F. Finish your sightseeing early on the 11th (Sat) to allow enough time to drive to Ashland.

Things to do in Newport

Parks · Historic Sites · Wildlife · Outdoors

Side Trips

Find places to stay Jun 8 — 11:

Ashland

— 2 nights
Ashland is a city in Jackson County, in the State of Oregon. Start off your visit on the 12th (Sun): relax and float downstream with a rafting and tubing tour, learn about winemaking at Grizzly Peak Winery, and then stroll around Lithia Park. Here are some ideas for day two: see a show at Oregon Shakespeare Festival and then get a taste of the local shopping with The Glass Forge.

For other places to visit, maps, traveler tips, and other tourist information, refer to the Ashland holiday tool.

Getting from Newport to Ashland by car takes about 5 hours. Other options: do a combination of bus and flight; or take a bus. Traveling from Newport in June, expect nights in Ashland to be somewhat warmer, around 55°F, while days are much warmer, around 86°F. Cap off your sightseeing on the 13th (Mon) early enough to go by car to Crater Lake National Park.

Things to do in Ashland

Museums · Adventure · Nightlife · Parks

Side Trip

Find places to stay Jun 11 — 13:

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 14th (Tue): explore the striking landscape of Crater Lake National Park.

To see reviews, ratings, and tourist information, use the Crater Lake National Park trip planning website.

You can drive from Ashland to Crater Lake National Park in 2 hours. Another option is to do a combination of bus and taxi. In June, daytime highs in Crater Lake National Park are 86°F, while nighttime lows are 55°F. Wrap up your sightseeing on the 14th (Tue) early enough to drive to Bend.

Things to do in Crater Lake National Park

Nature · Parks
Find places to stay Jun 13 — 14:
Highlights from your trip

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). Next up on the itinerary: let the river carry you with a rafting and tubing tour, hike along Falls Creek Trail to Green Lake, delve into the lush surroundings at Deschutes National Forest, and examine the collection at High Desert Museum.

To see maps, other places to visit, photos, and tourist information, you can read our Bend trip maker.

Getting from Crater Lake National Park to Bend by car takes about 2.5 hours. Other options: do a combination of taxi and bus. Traveling from Crater Lake National Park in June, things will get slightly colder in Bend: highs are around 75°F and lows about 45°F. Wrap up your sightseeing on the 17th (Fri) to allow time to fly to Hood River.

Things to do in Bend

Parks · Nature · Outdoors · Museums

Side Trips

Find places to stay Jun 14 — 17:

Hood River

— 3 nights
The city of Hood River is the seat of Hood River County, Oregon, United States. Venture out of the city with trips to Bonneville Lock & Dam (in Cascade Locks) and Timberline Lodge and Ski Area (in Timberline Lodge). There's still lots to do: explore the activities along Columbia River Gorge National Scenic Area, get impressive views of Mount Hood, hike along Historic Columbia River Highway State Trail, and examine the collection at Western Antique Aeroplane & Automobile Museum.

For traveler tips, photos, more things to do, and more tourist information, refer to the Hood River trip itinerary planner.

You can fly from Bend to Hood River in 2.5 hours. Other options are to drive; or take a bus. Traveling from Bend in June, plan for a bit warmer nights in Hood River, with lows around 55°F. Finish your sightseeing early on the 20th (Mon) so you can drive to Portland.

Things to do in Hood River

Parks · Nature · Winter Sports · Outdoors

Side Trips

Find places to stay Jun 17 — 20:

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.
Change things up with these side-trips from Portland: Cellar Door Wine Tours (in Lafayette) and Multnomah Falls (in Bridal Veil). Next up on the itinerary: admire the natural beauty at International Rose Test Garden, admire the striking features of Pittock Mansion, get to know the resident critters at Washington Park, and see the interesting displays at Oregon Museum of Science and Industry.

To see where to stay, more things to do, photos, and more tourist information, you can read our Portland trip builder tool.

Traveling by car from Hood River to Portland takes 1.5 hours. Alternatively, you can take a bus; or take a train. In June, daytime highs in Portland are 77°F, while nighttime lows are 56°F. Finish up your sightseeing early on the 24th (Fri) so you can travel back home.

Things to do in Portland

Parks · Tours · Zoos & Aquariums · Wineries

Side Trips

Find places to stay Jun 20 — 24:

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.