29 days in Oregon Itinerary

29 days in Oregon Itinerary

Created using Inspirock Oregon journey planner
Make it your trip
Drive
1
Hood River
— 2 nights
Drive
2
Portland
— 5 nights
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3
Astoria
— 3 nights
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4
Newport
— 4 nights
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5
Florence
— 4 nights
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6
Ashland
— 2 nights
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7
Crater Lake National Park
— 4 nights
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8
Bend
— 4 nights
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Hood River — 2 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 Government Camp). Next up on the itinerary: explore the activities along Columbia River Gorge National Scenic Area, examine the collection at Columbia Gorge Discovery Center & Museum, hit the slopes at Mount Hood, and admire the majestic nature at Starvation Creek State Park.

To see where to stay and more tourist information, use the Hood River day trip website.

Redmond to Hood River is an approximately 2.5-hour car ride. When traveling from Redmond in June, plan for little chillier days and a bit warmer nights in Hood River: temperatures range from 72°F by day to 55°F at night. Wrap up your sightseeing on the 3rd (Mon) to allow time to drive to Portland.
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Parks · Nature · Outdoors · Museums
Side Trips

Portland — 5 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: Multnomah Falls (in Bridal Veil) and Cellar Door Wine Tours (in Lafayette). The adventure continues: take in nature's colorful creations at International Rose Test Garden, get to know the resident critters at Oregon Zoo, look for gifts at Powell's City of Books, and admire the landmark architecture of Pittock Mansion.

For maps, where to stay, ratings, and more tourist information, you can 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. In June, plan for daily highs up to 77°F, and evening lows to 56°F. Finish your sightseeing early on the 8th (Sat) to allow enough time to drive to Astoria.
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Parks · Tours · Wineries · Zoos & Aquariums
Side Trips

Astoria — 3 nights

Spirit of the Columbia

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 (Cannon Beach, Haystack Rock, &more). Next up on the itinerary: identify plant and animal life at Astoria Column, explore the wealth of natural beauty at Fort Clatsop National Memorial, and immerse yourself in nature at Fort Stevens State Park.

To see photos, maps, other places to visit, and tourist information, use the Astoria trip planner.

You can drive from Portland to Astoria in 2 hours. Another option is to take a bus. When traveling from Portland in June, plan for a bit cooler days in Astoria, with highs around 66°F, while nights are about the same with lows around 52°F. Wrap up your sightseeing on the 11th (Tue) early enough to drive to Newport.
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Parks · Nature · Historic Sites · Outdoors
Side Trip

Newport — 4 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 (Yachats coastline & Bazalgette the Whale at Whale Park). And it doesn't end there: observe the fascinating underwater world at Oregon Coast Aquarium, explore the striking landscape at Cape Foulweather, get curious at Hatfield Marine Science Center, and kick back and relax at Nye Beach.

Inspirock's itinerary builder makes planning a Newport trip simple and quick.

Getting from Astoria to Newport by car takes about 3.5 hours. Other options: take a bus. Traveling from Astoria in June, expect nights in Newport to be about the same, around 48°F, while days are slightly colder, around 61°F. Finish your sightseeing early on the 15th (Sat) to allow enough time to drive to Florence.
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Parks · Outdoors · Beaches · Nature
Side Trips

Florence — 4 nights

Florence is a coastal city in Lane County, in the U.S. state of Oregon. Explore Florence's surroundings by going to Bandon (Circles in the Sand, Bandon Dunes Golf Resort, &more), Coos Bay (Cape Arago State Park & Shore Acres State Park) and Cape Perpetua Visitor Center - Siuslaw National Forest (in Yachats). There's much more to do: enjoy the sea views from Heceta Head Lighthouse, take in the dramatic natural features at Thor's Well, take a memorable drive along Oregon Coast Hwy, and experience the excitement of Sandland Adventures.

To see traveler tips, reviews, more things to do, and tourist information, you can read our Florence online trip itinerary maker.

You can drive from Newport to Florence in 1.5 hours. Another option is to take a bus. In June, daily temperatures in Florence can reach 65°F, while at night they dip to 52°F. Finish your sightseeing early on the 19th (Wed) to allow enough time to drive to Ashland.
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Parks · Outdoors · Nature · Scenic Drive
Side Trips

Ashland — 2 nights

Ashland is a city in Jackson County, in the State of Oregon. On the 20th (Thu), relax and float downstream with a rafting and tubing tour, then see a show at Oregon Shakespeare Festival, then stroll around Lithia Park, and finally look for gifts at Bloomsbury Books. Keep things going the next day: contemplate the waterfront views at Rogue River, then see the interesting displays at Bear Hotel Artworks Museum, then get a taste of the local shopping with The Glass Forge, and finally experience rural life at Seven Oaks Farm.

To see other places to visit, maps, more things to do, and more tourist information, go to the Ashland trip planner.

You can drive from Florence to Ashland in 4.5 hours. Other options are to take a bus; or take a bus. Traveling from Florence in June, expect nights in Ashland to be about the same, around 55°F, while days are much warmer, around 86°F. Wrap up your sightseeing on the 21st (Fri) to allow time to drive to Crater Lake National Park.
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Parks · Shopping · Museums · Adventure
Side Trips

Crater Lake National Park — 4 nights

Reaching a depth of 592 m (1,943 ft), Crater Lake is the deepest lake in the United States.
Get out of town with these interesting Crater Lake National Park side-trips: Prospect (Natural Bridge Viewpoint & Mill Creek Falls) and Collier Memorial State Park (in Chiloquin). Spend the 22nd (Sat) exploring nature at Crater Lake National Park. The adventure continues: take a memorable drive along Rim Dr, admire the sheer force of Toketee Falls, identify plant and animal life at Rogue River Gorge Viewpoint, and explore and take pictures at Rogue-Umpqua Scenic Byway.

To find more things to do, where to stay, other places to visit, and more tourist information, use the Crater Lake National Park trip maker website.

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 25th (Tue) to allow time to drive to Bend.
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Parks · Nature · Outdoors · Scenic Drive
Side Trips

Bend — 4 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 Bend's surroundings by going to Smith Rock State Park (in Redmond) and Sisters (Proxy Falls, Sahalie and Koosah Falls, &more). The adventure continues: take a tour by water with Boat Tours & Water Sports, walk around Pilot Butte State Scenic Viewpoint, see the interesting displays at High Desert Museum, and see the sky in a new way at Oregon Observatory.

For other places to visit, ratings, more things to do, and tourist information, refer to the Bend trip itinerary app.

Traveling by car from Crater Lake National Park to Bend takes 2.5 hours. Alternatively, you can do a combination of taxi and bus. In June, Bend is a bit cooler than Crater Lake National Park - with highs of 75°F and lows of 45°F. Wrap up your sightseeing on the 29th (Sat) early enough to drive back home.
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Parks · Outdoors · Nature · Museums
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.
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