31 days in Oregon Itinerary

31 days in Oregon Itinerary

Created using Inspirock Oregon trip itinerary planner

Make it your trip
Fly
1
Hood River
— 3 nights
Fly
2
Bend
— 5 nights
Drive
3
Crater Lake National Park
— 3 nights
Drive
4
Ashland
— 2 nights
Fly
5
Cannon Beach
— 3 nights
Drive
6
Newport
— 4 nights
Drive
7
Florence
— 4 nights
Fly
8
Portland
— 6 nights
Fly

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Hood River

— 3 nights
The city of Hood River is the seat of Hood River County, Oregon, United States. Bring the kids along to Columbia River Gorge National Scenic Area and Imperial River Company. Change things up with these side-trips from Hood River: River Rafting & Tubing (in Maupin), Timberline Lodge and Ski Area (in Timberline Lodge) and Bonneville Lock & Dam (in Cascade Locks). There's still lots to do: take a memorable drive along Hood River County Fruit Loop, tour the pleasant surroundings at Horsetail Falls- Columbia River Gorge, take your sightseeing to a higher altitude at Mount Hood, and see the interesting displays at Western Antique Aeroplane & Automobile Museum.

To see other places to visit, maps, ratings, and other tourist information, read Hood River online holiday planner.

Orlando to Hood River is an approximately 8-hour flight. You can also drive; or do a combination of bus and train. Traveling from Orlando to Hood River, you'll gain 3 hours due to the time zone difference. Traveling from Orlando in July, things will get slightly colder in Hood River: highs are around 79°F and lows about 58°F. Cap off your sightseeing on the 4th (Sun) early enough to catch the flight to Bend.

Things to do in Hood River

Outdoors · Parks · Nature · Wildlife

Side Trips

Bend

— 5 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.
Bring the kids along to River Rafting & Tubing and Oregon Observatory. Get out of town with these interesting Bend side-trips: Smith Rock State Park (in Redmond), Fall River Trail (in Sunriver) and Sisters (Sahalie and Koosah Falls, City of Sisters, &more). And it doesn't end there: explore the activities along Deschutes River, see the sky in a new way at Dee Wright Observatory, Head underground at Lava River Cave, and see the interesting displays at High Desert Museum.

To see where to stay, reviews, photos, and tourist information, read our Bend trip planner.

You can fly from Hood River to Bend in 2.5 hours. Alternatively, you can drive; or take a bus. Expect somewhat warmer weather when traveling from Hood River in July: highs in Bend hover around 85°F, while lows dip to 52°F. Wrap up your sightseeing on the 9th (Fri) to allow time to drive to Crater Lake National Park.

Things to do in Bend

Parks · Nature · Outdoors · Museums

Side Trips

Crater Lake National Park

— 3 nights
Reaching a depth of 592 m (1,943 ft), Crater Lake is the deepest lake in the United States.
Take a break from Crater Lake National Park with a short trip to Collier Memorial State Park in Chiloquin, about 36 minutes away. Spend the 10th (Sat) exploring nature at Crater Lake National Park. There's still lots to do: cruise along Rim Dr, tour the pleasant surroundings at Rogue River Gorge Viewpoint, admire all the interesting features of Rogue-Umpqua Scenic Byway, and trek along Cleetwood Cove Trail.

To find reviews, more things to do, where to stay, and more tourist information, use the Crater Lake National Park trip itinerary planning website.

Traveling by car from Bend to Crater Lake National Park takes 2.5 hours. Alternatively, you can do a combination of bus and taxi. In July, Crater Lake National Park is a bit warmer than Bend - with highs of 94°F and lows of 61°F. Wrap up your sightseeing on the 12th (Mon) to allow time to drive to Ashland.

Things to do in Crater Lake National Park

Parks · Nature · Outdoors · Scenic Drive

Side Trips

Ashland

— 2 nights
Ashland is a city in Jackson County, in the State of Oregon. Kick off your visit on the 13th (Tue): stroll around North Mountain Park, stroll around Lithia Park, catch a live performance at Oregon Shakespeare Festival, then let the river carry you with a rafting and tubing tour, and finally explore the engaging exhibits at ScienceWorks Hands-On Museum. Keep things going the next day: view the masterpieces at The Glass Forge, see the interesting displays at Bear Hotel Artworks Museum, then explore the activities along Rogue River, then hike along Natural Bridge Loop, and finally contemplate the long history of Historic Pinehurst Inn.

For reviews, more things to do, maps, and more tourist information, you can read our Ashland trip itinerary maker site.

You can drive from Crater Lake National Park to Ashland in 2 hours. Another option is to do a combination of taxi and bus. Expect a daytime high around 94°F in July, and nighttime lows around 61°F. Wrap up your sightseeing on the 14th (Wed) early enough to fly to Cannon Beach.

Things to do in Ashland

Parks · Outdoors · Adventure · Tours

Side Trips

Cannon Beach

— 3 nights
Cannon Beach is a city in Clatsop County, Oregon, United States. Visit Haystack Rock and Manzanita Beach for some beach relaxation. Attractions like Cannon Beach and Hug Point State Park make great kid-friendly stops. Explore Cannon Beach's surroundings by going to Cape Lookout State Park (in Tillamook) and Rockaway Beach (Rockaway Beach Wayside & Kelly's Brighton Marina). There's still lots to do: immerse yourself in nature at Ecola State Park, enjoy the sand and surf at Short Sands Beach, shop like a local with Icefire Glassworks, and tour the pleasant surroundings at Tolovana Beach State Recreation Site.

To find other places to visit, reviews, maps, and more tourist information, refer to the Cannon Beach day trip tool.

You can fly from Ashland to Cannon Beach in 2.5 hours. Alternatively, you can drive; or take a bus. When traveling from Ashland in July, plan for cooler days and a bit cooler nights in Cannon Beach: temperatures range from 69°F by day to 55°F at night. Finish your sightseeing early on the 17th (Sat) so you can drive to Newport.

Things to do in Cannon Beach

Parks · Nature · Outdoors · Beaches

Side Trips

Newport

— 4 nights
A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
You'll visit kid-friendly attractions like Oregon Coast Aquarium and Nye Beach. We've included these beaches for you: Cape Kiwanda State Natural Area and Devils Punchbowl State Natural Area. Change things up with these side-trips from Newport: Lincoln City (Taft Bay, Roads End State Recreation Site, &more), Yachats coastline (in Yachats) and Gleneden Beach State Park (in Gleneden Beach). Next up on the itinerary: tour the pleasant surroundings at Yaquina Head Outstanding Natural Area, enjoy the sea views from Yaquina Head Lighthouse, make a trip to Yaquina Bay Bridge, and immerse yourself in nature at South Beach State Park.

To see where to stay, maps, and more tourist information, refer to the Newport online travel route planner.

You can drive from Cannon Beach to Newport in 3 hours. Another option is to take a bus. Traveling from Cannon Beach in July, expect Newport to be slightly colder, temps between 63°F and 50°F. Finish your sightseeing early on the 21st (Wed) to allow enough time to drive to Florence.

Things to do in Newport

Parks · Outdoors · Beaches · Nature

Side Trips

Florence

— 4 nights
Florence is a coastal city in Lane County, in the U.S. state of Oregon. Visit Coquille Point and Heceta Beach for some beach relaxation. Kids will enjoy Sandland Adventures and Wildlife Safari. Venture out of the city with trips to Golden and Silver Falls State Natural Area (in Allegany), Cape Perpetua Visitor Center - Siuslaw National Forest (in Yachats) and Shore Acres State Park (in Coos Bay). There's much more to do: explore the fascinating underground world of Sea Lion Caves, snap pictures at Siuslaw River Bridge, kick back and relax at Bandon State Park, and enjoy the sea views from Heceta Head Lighthouse.

For maps, reviews, photos, and other tourist information, refer to the Florence online tour planner.

Getting from Newport to Florence by car takes about 1.5 hours. Other options: take a bus. Expect a daytime high around 67°F in July, and nighttime lows around 54°F. Finish your sightseeing early on the 25th (Sun) so you can fly to Portland.

Things to do in Florence

Parks · Nature · Outdoors · Wildlife

Side Trips

Portland

— 6 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.
You'll visit kid-friendly attractions like International Rose Test Garden and Oregon Zoo. You'll find plenty of places to visit near Portland: Astoria (Cathedral Tree Trail & Astoria Column), Seaside Aquarium (in Seaside) and Multnomah Falls (in Bridal Veil). There's much more to do: look for gifts at Powell's City of Books, see the interesting displays at Evergreen Aviation & Space Museum, take in nature's colorful creations at Lan Su Chinese Garden, and explore the engaging exhibits at Portland Children's Museum.

To find where to stay, photos, ratings, and tourist information, read our Portland tour planner.

Traveling by flight from Florence to Portland takes 2.5 hours. Alternatively, you can drive; or take a bus. Traveling from Florence in July, expect nights in Portland to be about the same, around 59°F, while days are a bit warmer, around 83°F. Wrap up your sightseeing by early afternoon on the 31st (Sat) to allow enough time to fly back home.

Things to do in Portland

Parks · Outdoors · Museums · Trails

Side Trips

Oregon travel guide

4.4
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.