14 days in Oregon Itinerary

14 days in Oregon Itinerary

Created using Inspirock Oregon tour planner

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

S M T W T F S
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Cannon Beach

— 1 night
Cannon Beach is a city in Clatsop County, Oregon, United States. On the 8th (Sun), view the masterpieces at Icefire Glassworks, then explore the striking landscape at Haystack Rock, and then stroll through Cannon Beach. Keep things going the next day: immerse yourself in nature at Ecola State Park and then admire the majestic nature at Oswald West State Park.

To find more things to do, maps, photos, and more tourist information, read Cannon Beach travel planning tool.

Portland to Cannon Beach is an approximately 1.5-hour car ride. You can also take a bus. Prepare for a bit cooler weather when traveling from Portland in August: high temperatures in Cannon Beach hover around 71°F and lows are around 55°F. Finish your sightseeing early on the 9th (Mon) so you can fly to Ashland.

Things to do in Cannon Beach

Parks · Nature · Beaches · Outdoors

Ashland

— 1 day
Ashland is a city in Jackson County, in the State of Oregon. On the 10th (Tue), explore the activities along Rogue River and then relax and float downstream with a rafting and tubing tour.

To see where to stay, maps, other places to visit, and more tourist information, refer to the Ashland trip planner.

You can fly from Cannon Beach to Ashland in 2.5 hours. Alternatively, you can drive; or take a bus. Traveling from Cannon Beach in August, you will find days in Ashland are much hotter (93°F), and nights are about the same (60°F). Wrap up your sightseeing on the 10th (Tue) to allow time to drive to Crater Lake National Park.

Things to do in Ashland

Parks · Nature · Tours · Outdoors

Side Trip

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.
On the 11th (Wed), explore the wealth of natural beauty at Crater Lake National Park.

To find ratings, reviews, other places to visit, and more tourist information, use the Crater Lake National Park trip itinerary planner.

You can drive from Ashland to Crater Lake National Park in 2 hours. Alternatively, you can do a combination of bus and taxi. In August, plan for daily highs up to 93°F, and evening lows to 60°F. Finish your sightseeing early on the 11th (Wed) to allow enough time to drive to Bend.

Things to do in Crater Lake National Park

Parks · Nature
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.
Explore Bend's surroundings by going to McKenzie Pass-Santiam Pass loop (in Sisters) and Smith Rock State Park (in Redmond). The adventure continues: let the river carry you with a rafting and tubing tour, delve into the lush surroundings at Deschutes National Forest, examine the collection at High Desert Museum, and explore the activities along Deschutes River.

To find more things to do, traveler tips, ratings, and more tourist information, you can read our Bend road trip planning 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. Traveling from Crater Lake National Park in August, expect Bend to be slightly colder, temps between 84°F and 52°F. Finish your sightseeing early on the 14th (Sat) so you can fly to Hood River.

Things to do in Bend

Parks · Nature · Outdoors · Museums

Side Trips

Hood River

— 2 nights
The city of Hood River is the seat of Hood River County, Oregon, United States. Kick off your visit on the 15th (Sun): contemplate the geological forces at Mount Hood and then contemplate the waterfront views at Trillium Lake. Get ready for a full day of sightseeing on the next day: explore the activities along Columbia River Gorge National Scenic Area and then admire the engineering at Bonneville Lock & Dam.

To find photos, maps, and tourist information, read Hood River day trip planning site.

Fly from Bend to Hood River in 2.5 hours. Alternatively, you can drive; or take a bus. Traveling from Bend in August, Hood River is a bit warmer at night with lows of 60°F. Wrap up your sightseeing on the 16th (Mon) early enough to fly to Florence.

Things to do in Hood River

Parks · Nature · Wildlife · Outdoors

Side Trips

Florence

— 2 nights
Florence is a coastal city in Lane County, in the U.S. state of Oregon. Start off your visit on the 17th (Tue): explore the fascinating underground world of Sea Lion Caves and then get the adrenaline pumping with Sandland Adventures. On the 18th (Wed), you'll have a packed day of sightseeing: admire all the interesting features of Cape Perpetua Visitor Center - Siuslaw National Forest and then take a leisurely stroll along Yachats coastline.

To find maps, reviews, ratings, and more tourist information, read Florence trip itinerary maker tool.

Getting from Hood River to Florence by flight takes about 2.5 hours. Other options: drive; or take a bus. In August, Florence is slightly colder than Hood River - with highs of 68°F and lows of 54°F. Finish your sightseeing early on the 18th (Wed) to allow enough time to fly to Portland.

Things to do in Florence

Parks · Nature · Outdoors · Fun & Games

Side Trip

Portland

— 3 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: Oneonta Gorge (in Cascade Locks) and Multnomah Falls (in Bridal Veil). The adventure continues: admire the natural beauty at Portland Japanese Garden, head outdoors with Portland Timbers, stroll around Tom McCall Waterfront Park, and get to know the resident critters at Oregon Zoo.

To find maps, where to stay, traveler tips, and tourist information, refer to the Portland trip planner.

You can fly from Florence to Portland in 2.5 hours. Alternatively, you can drive; or take a bus. Traveling from Florence in August, things will get somewhat warmer in Portland: highs are around 85°F and lows about 60°F. Wrap up your sightseeing on the 21st (Sat) early enough to travel back home.

Things to do in Portland

Parks · Nature · Outdoors · 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.