14 days in Oregon Itinerary

14 days in Oregon Itinerary

Created using Inspirock Oregon tour itinerary builder

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Route & dates

14 days in Oregon Itinerary

Start: Fort Smith
Fly:  8​h 30​min
1
Portland
— 3 nights
Drive:  1​h 30​min
2
Cannon Beach
— 2 nights
Drive:  4​h
3
Florence
— 2 nights
Drive:  4​h 15​min
4
Ashland
— 1 night
Drive:  4​h 30​min
5
Bend
— 3 nights
Drive:  3​h 15​min
6
Hood River
— 2 nights
Drive + Fly:  9​h 30​min
End: Fort Smith

3
nights
Portland

Portland ©
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.
Venture out of the city with trips to Multnomah Falls (in Bridal Veil) and Evergreen Aviation & Space Museum (in McMinnville). The adventure continues: take in nature's colorful creations at Portland Japanese Garden, don't miss a visit to Pioneer Courthouse Square, stroll around South Park Blocks, and look for gifts at Powell's City of Books.

To see traveler tips, more things to do, and tourist information, go to the Portland trip planner .

Fort Smith to Portland is an approximately 8.5-hour flight. You can also drive. Due to the time zone difference, you'll gain 2 hours traveling from Fort Smith to Portland. Traveling from Fort Smith in July, things will get slightly colder in Portland: highs are around 83°F and lows about 59°F. Cap off your sightseeing on the 30th (Tue) early enough to go by car to Cannon Beach.

Things to do in Portland

Parks Tours Museums

Side Trips

Multnomah Falls, Evergreen Aviation & Space Museum
Highlights from your plan
Portland Japanese Garden ©
Portland Japanese Garden
International Rose Test Garden ©
International Rose Test Garden
Powell's City of Books ©
Powell's City of Books

2
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. On the 31st (Wed), enjoy the sand and surf at Haystack Rock, immerse yourself in nature at Ecola State Park, then pause for some photo ops at Seaside Beach Lewis and Clark Monument, and finally pause for some photo ops at Astoria Column. On your second day here, snap pictures at Astoria-Megler Bridge, immerse yourself in nature at Oswald West State Park, and then enjoy the sand and surf at Cannon Beach.

For ratings, reviews, maps, and other tourist information, you can read our Cannon Beach trip itinerary website .

Traveling by car from Portland to Cannon Beach takes 1.5 hours. Alternatively, you can take a bus. Expect slightly colder weather when traveling from Portland in July: highs in Cannon Beach hover around 69°F, while lows dip to 55°F. Finish your sightseeing early on the 1st (Thu) so you can drive to Florence.

Things to do in Cannon Beach

Parks Nature Outdoors

Side Trips

Astoria, Seaside Beach Lewis and Clark Monument
Highlights from your plan
Haystack Rock ©
Haystack Rock
Ecola State Park ©
Ecola State Park
Cannon Beach ©
Cannon Beach

2
nights
Florence

Florence ©
Florence is a coastal city in Lane County, in the U.S. Kick off your visit on the 2nd (Fri): immerse yourself in nature at Cape Perpetua Visitor Center - Siuslaw National Forest, take in the waterfront at Yachats coastline, then visit a coastal fixture at Heceta Head Lighthouse, and finally make a trip to Siuslaw River Bridge. Get ready for a full day of sightseeing on the 3rd (Sat): Head underground at Sea Lion Caves, have fun at Sand Master Park, and then try for a hole-in-one at Sandland Adventures.

To see maps, photos, ratings, and other tourist information, use the Florence trip planner .

Traveling by car from Cannon Beach to Florence takes 4 hours. Alternatively, you can do a combination of bus and flight; or take a bus. In August, daytime highs in Florence are 68°F, while nighttime lows are 54°F. Finish your sightseeing early on the 3rd (Sat) to allow enough time to drive to Ashland.

Things to do in Florence

Nature Outdoors Parks

Side Trip

Yachats
Highlights from your plan
Yachats coastline ©
Yachats coastline
Sand Master Park - Sandboarding ©
Sand Master Park - Sandboarding

1
night
Ashland

Ashland is a city in Jackson County, in the State of Oregon. On the 4th (Sun), stroll around Lithia Park, then have fun and explore at ScienceWorks Hands-on Museum, and then let the river carry you with a rafting and tubing tour.

Plan a trip to Ashland easily and quickly by telling Inspirock to suggest an itinerary.

Traveling by car from Florence to Ashland takes 4.5 hours. Alternatively, you can take a bus; or do a combination of bus and flight. Traveling from Florence in August, expect nights in Ashland to be somewhat warmer, around 60°F, while days are much warmer, around 93°F. Finish your sightseeing early on the 4th (Sun) so you can drive to Bend.

Things to do in Ashland

Outdoors Tours Adventure
Highlights from your plan
River Rafting & Tubing
Lithia Park ©
Lithia Park
ScienceWorks Hands-On Museum ©
ScienceWorks Hands-On Museum

3
nights
Bend

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: Smith Rock State Park (in Redmond) and Artists Gallery Sunriver (in Sunriver). And it doesn't end there: learn more about the world around you at High Desert Museum, indulge your thirst for a good beer at Atlas Cider Co, take a peaceful walk through Deschutes National Forest, and see the sky in a new way at Oregon Observatory.

To find ratings and tourist information, go to the Bend driving holiday planner.

You can drive from Ashland to Bend in 4.5 hours. Other options are to do a combination of bus and flight; or take a bus. Traveling from Ashland in August, expect Bend to be slightly colder, temps between 84°F and 52°F. Wrap up your sightseeing on the 7th (Wed) to allow time to drive to Hood River.

Things to do in Bend

Parks Nature Museums

Side Trips

Sunriver, Smith Rock State Park
Highlights from your plan
Smith Rock State Park ©
Smith Rock State Park
River Rafting & Tubing
High Desert Museum ©
High Desert Museum

2
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. On the 8th (Thu), examine the collection at Western Antique Aeroplane & Automobile Museum, identify plant and animal life at Columbia River Gorge National Scenic Area, and then take in the views from Bridge of the Gods.

To see maps, reviews, where to stay, and more tourist information, refer to the Hood River online trip builder .

You can drive from Bend to Hood River in 3.5 hours. Alternatively, you can do a combination of flight and bus; or take a bus. Traveling from Bend in August, you can expect nighttime temperatures to be somewhat warmer in Hood River, with lows of 60°F. Wrap up your sightseeing by early afternoon on the 9th (Fri) to allow time for travel back home.

Things to do in Hood River

Nature Parks Wildlife

Side Trips

Bridge of the Gods, Columbia Gorge Discovery Center & Museum, Columbia River Gorge National Scenic Area
Highlights from your plan

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