31 days in Oregon Itinerary

31 days in Oregon Itinerary

Created using Inspirock Oregon tour itinerary maker

Plan created by another user. Make it yours
Fly
1
Bend
— 3 nights
Drive
2
Crater Lake National Park
— 4 nights
Drive
3
Ashland
— 3 nights
Drive
4
Coos Bay
— 2 nights
Drive
5
Newport
— 4 nights
Drive
6
Astoria
— 4 nights
Drive
7
Hood River
— 4 nights
Drive
8
Portland
— 6 nights
Fly

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3
nights
Bend

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.
You'll find plenty of places to visit near Bend: Sisters (Sahalie and Koosah Falls & McKenzie Pass-Santiam Pass loop), Smith Rock State Park (in Redmond) and Dee Wright Observatory (in Blue River). The adventure continues: relax and float downstream with a rafting and tubing tour, walk around Drake Park, contemplate the waterfront views at Deschutes River, and see the interesting displays at High Desert Museum.

To find photos, maps, ratings, and other tourist information, read Bend trip planner.

Pittsburgh to Bend is an approximately 10.5-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 Pittsburgh to Bend. Traveling from Pittsburgh in June, plan for slightly colder nights in Bend, with lows around 45°F. Cap off your sightseeing on the 23rd (Wed) early enough to go by car to Crater Lake National Park.

Things to do in Bend

Parks · Nature · Museums · Outdoors

Side Trips

4
nights
Crater Lake National Park

Reaching a depth of 592 m (1,943 ft), Crater Lake is the deepest lake in the United States.
Explore Crater Lake National Park's surroundings by going to Prospect (Natural Bridge Viewpoint & Mill Creek Falls). Spend the 24th (Thu) exploring nature at Crater Lake National Park. There's much more to do: cruise along Rim Dr, admire the sheer force of Whitehorse Falls, trek along Garfield Peak, and head off the coast to Wizard Island.

For maps, reviews, where to stay, and other tourist information, use the Crater Lake National Park trip planner.

Drive from Bend to Crater Lake National Park in 2.5 hours. Alternatively, you can do a combination of bus and taxi. Traveling from Bend in June, things will get somewhat warmer in Crater Lake National Park: highs are around 86°F and lows about 55°F. Finish your sightseeing early on the 27th (Sun) so you can drive to Ashland.

Things to do in Crater Lake National Park

Parks · Nature · Outdoors · Trails

Side Trips

3
nights
Ashland

Ashland is a city in Jackson County, in the State of Oregon. Explore the numerous day-trip ideas around Ashland: Cave Junction (Siskiyou Smokejumper Base Museum & Oregon Caves National Monument and Preserve), Rogue River (in Medford) and Grants Pass (Wildlife Images - Rehabilitation & Education Center & The Glass Forge). There's lots more to do: relax and float downstream with a rafting and tubing tour, see a show at Oregon Shakespeare Festival, view the masterpieces at Gathering Glass Studio, and admire the masterpieces at Schneider Museum of Art.

For maps, reviews, traveler tips, and more tourist information, read Ashland trip builder website.

You can drive from Crater Lake National Park to Ashland in 2 hours. Another option is to 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 30th (Wed) to allow enough time to travel to Coos Bay.

Things to do in Ashland

Parks · Nature · Museums · Outdoors

Side Trips

2
nights
Coos Bay

Coos Bay is a city located in Coos County, Oregon, United States, where the Coos River enters Coos Bay on the Pacific Ocean. Start off your visit on the 1st (Thu): explore the striking landscape at Face Rock State Scenic Viewpoint and then admire the majestic nature at Shore Acres State Park. On the next day, play a few rounds at Bandon Dunes Golf Resort, make a trip to Steve Prefontaine Murals, then relax in the rural setting at Cranberry Sweets, and finally admire the majestic nature at Cape Arago State Park.

To see traveler tips, reviews, more things to do, and other tourist information, go to the Coos Bay road trip planner.

Getting from Ashland to Coos Bay by car takes about 3.5 hours. When traveling from Ashland in June, plan for cooler days in Coos Bay, with highs around 65°F, while nights are about the same with lows around 52°F. Wrap up your sightseeing on the 2nd (Fri) to allow time to travel to Newport.

Things to do in Coos Bay

Parks · Nature · Outdoors · Wildlife

Side Trip

4
nights
Newport

A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
Explore the numerous day-trip ideas around Newport: Yachats (Cape Perpetua Visitor Center - Siuslaw National Forest & Yachats coastline), Florence (Heceta Head Lighthouse, Strawberry Hill Wayside, &more) and Rock Your World: Pacific Northwest Gem & Jewelry Gallery (in Lincoln City). Next up on the itinerary: identify plant and animal life at Yaquina Head Outstanding Natural Area, take in the waterfront at Newport's Historic Bayfront, take a memorable drive along Otter Crest Loop, and visit a coastal fixture at Yaquina Head Lighthouse.

To find maps, reviews, more things to do, and tourist information, read our Newport driving holiday planner.

Getting from Coos Bay to Newport by car takes about 2.5 hours. In July, daytime highs in Newport are 63°F, while nighttime lows are 50°F. Cap off your sightseeing on the 6th (Tue) early enough to go by car to Astoria.

Things to do in Newport

Parks · Outdoors · Nature · Scenic Drive

Side Trips

4
nights
Astoria

Spirit of the Columbia

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 (Hug Point State Park, Haystack Rock, &more) and Nehalem Bay State Park (in Nehalem). And it doesn't end there: pause for some photo ops at Astoria Column, stroll through Fort Clatsop National Memorial, examine the collection at Seaside Inverted Experience, and immerse yourself in nature at Fort Stevens State Park.

To find other places to visit, traveler tips, more things to do, and more tourist information, go to the Astoria trip itinerary planner.

You can drive from Newport to Astoria in 3.5 hours. Alternatively, you can take a bus. While traveling from Newport, expect somewhat warmer days and about the same nights in Astoria, ranging from highs of 69°F to lows of 55°F. Finish your sightseeing early on the 10th (Sat) to allow enough time to drive to Hood River.

Things to do in Astoria

Parks · Nature · Historic Sites · Outdoors

Side Trips

4
nights
Hood River

The city of Hood River is the seat of Hood River County, Oregon, United States. Change things up with these side-trips from Hood River: Bonneville Lock & Dam (in Cascade Locks) and Timberline Lodge and Ski Area (in Timberline Lodge). The adventure continues: look for all kinds of wild species at Columbia River Gorge National Scenic Area, brush up on your military savvy at Fort Dalles Museum and Anderson Homestead, cruise along Hood River County Fruit Loop, and see the interesting displays at Western Antique Aeroplane & Automobile Museum.

For more things to do, other places to visit, traveler tips, and tourist information, go to the Hood River trip itinerary builder tool.

Traveling by car from Astoria to Hood River takes 3 hours. Alternatively, you can take a bus; or do a combination of bus and train. When traveling from Astoria in July, plan for a bit warmer days in Hood River, with highs around 79°F, while nights are about the same with lows around 58°F. Finish up your sightseeing early on the 14th (Wed) so you can go by car to Portland.

Things to do in Hood River

Parks · Outdoors · Nature · Museums

Side Trips

6
nights
Portland

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.
Explore Portland's surroundings by going to Cellar Door Wine Tours (in Lafayette), Multnomah Falls (in Bridal Veil) and Evergreen Aviation & Space Museum (in McMinnville). Next up on the itinerary: take in nature's colorful creations at International Rose Test Garden, examine the collection at Oregon Museum of Science and Industry, trek along Forest Park, and learn the secrets of beer at a beer tour and tasting.

To find maps, other places to visit, ratings, and tourist information, read our Portland day trip tool.

Traveling by car from Hood River to Portland takes 1.5 hours. Alternatively, you can take a bus; or take a train. Expect a daytime high around 83°F in July, and nighttime lows around 59°F. You will have some time to spend on the 20th (Tue) before leaving for home.

Things to do in Portland

Parks · Tours · Museums · Wineries

Side Trips

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.