14 days in Oregon Itinerary

14 days in Oregon Itinerary

Created using Inspirock Oregon itinerary planner

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Route & dates

14 days in Oregon Itinerary

Start: Vancouver
Fly:  4​h 15​min
1
Portland
— 3 nights
bus:  1​h 15​min
2
Hood River
— 2 nights
Drive:  3​h
3
Cannon Beach
— 3 nights
Drive:  2​h 45​min
4
Newport
— 2 nights
Drive:  4​h 30​min
5
Bend
— 3 nights
Fly:  6​h
End: Vancouver

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.
Take a break from Portland with a short trip to Multnomah Falls in Bridal Veil, about 38 minutes away. Dedicate the 7th (Sat) to wine at some of the top wineries in the area. Next up on the itinerary: take in nature's colorful creations at Portland Japanese Garden, get to know the resident critters at Oregon Zoo, indulge your taste buds at Food & Drink, and stroll around Tom McCall Waterfront Park.

Find out how to plan Portland trip without stress by asking Inspirock to help create an itinerary.

Vancouver, Canada to Portland is an approximately 4.5-hour flight. You can also do a combination of shuttle and flight; or drive. Traveling from Vancouver in September, you will find days in Portland are somewhat warmer (28°C), and nights are about the same (15°C). Wrap up your sightseeing on the 8th (Sun) early enough to take a bus to Hood River.

Things to do in Portland

Tours Parks Zoos & Aquariums

Side Trip

Multnomah Falls
Highlights from your plan
Portland Japanese Garden ©
Portland Japanese Garden
Powell's City of Books ©
Powell's City of Books
International Rose Test Garden ©
International Rose Test Garden

2
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. Kick off your visit on the 9th (Mon): see the interesting displays at Western Antique Aeroplane & Automobile Museum, then explore the activities along Columbia River Gorge National Scenic Area, and then learn about winemaking at Marchesi Vineyards. Get ready for a full day of sightseeing on the 10th (Tue): see human ingenuity at work at Bonneville Lock & Dam, see the interesting displays at Columbia Gorge Discovery Center & Museum, and then trek along Historic Columbia River Highway State Trail.

To see where to stay, maps, other places to visit, and more tourist information, go to the Hood River online trip builder .

Getting from Portland to Hood River by bus takes about 1.5 hours. Other options: drive; or take a train. Expect slightly colder weather when traveling from Portland in September: highs in Hood River hover around 25°C, while lows dip to 16°C. Finish your sightseeing early on the 10th (Tue) so you can drive to Cannon Beach.

Things to do in Hood River

Parks Wildlife Nature

Side Trips

Columbia River Gorge National Scenic Area, Columbia Gorge Discovery Center & Museum, Bonneville Lock & Dam, Historic Columbia River Highway State Trail
Highlights from your plan

3
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. You'll find plenty of places to visit near Cannon Beach: Astoria (Astoria Column, Fort Stevens State Park, & more). And it doesn't end there: take in the dramatic natural features at Haystack Rock, see the interesting displays at Seaside Inverted Experience, immerse yourself in nature at Ecola State Park, and stroll through Cannon Beach.

To see ratings, where to stay, traveler tips, and tourist information, you can read our Cannon Beach trip itinerary website .

Drive from Hood River to Cannon Beach in 3 hours. Alternatively, you can take a bus; or do a combination of train and bus. Expect a bit cooler evenings in Cannon Beach when traveling from Hood River in September, with lows around 13°C. Cap off your sightseeing on the 13th (Fri) early enough to go by car to Newport.

Things to do in Cannon Beach

Parks Nature Beaches

Side Trips

Astoria, Seaside
Highlights from your plan
Haystack Rock ©
Haystack Rock
Ecola State Park ©
Ecola State Park
Cannon Beach ©
Cannon Beach

2
nights
Newport

Newport ©
A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
On the 14th (Sat), take a leisurely stroll along Yachats coastline, then cruise along Cape Perpetua Visitor Center - Siuslaw National Forest, and then take a leisurely stroll along Newport's Historic Bayfront. Keep things going the next day: observe the fascinating underwater world at Oregon Coast Aquarium, enjoy the sea views from Yaquina Head Lighthouse, and then look for all kinds of wild species at Yaquina Head Outstanding Natural Area.

For maps, traveler tips, ratings, and more tourist information, refer to the Newport trip maker .

You can drive from Cannon Beach to Newport in 3 hours. Another option is to take a bus. Traveling from Cannon Beach in September, you will find days in Newport are slightly colder (20°C), and nights are about the same (11°C). Wrap up your sightseeing on the 15th (Sun) early enough to drive to Bend.

Things to do in Newport

Parks Wildlife Scenic Drive

Side Trip

Yachats
Highlights from your plan
Yachats coastline ©
Yachats coastline
Yaquina Head Outstanding Natural Area ©

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.
Get out of town with these interesting Bend side-trips: Smith Rock State Park (in Redmond), McKenzie Pass-Santiam Pass loop (in Sisters) and Dee Wright Observatory (in Blue River). There's still lots to do: get a new perspective on nature at High Desert Museum, view the masterpieces at Artists Gallery Sunriver, look and learn at Oregon Observatory, and walk around Drake Park.

To find ratings, traveler tips, other places to visit, and tourist information, you can read our Bend travel route website .

Getting from Newport to Bend by car takes about 4.5 hours. Other options: take a bus. While traveling from Newport, expect a bit warmer days and a bit cooler nights in Bend, ranging from highs of 26°C to lows of 7°C. Wrap up your sightseeing on the 18th (Wed) early enough to travel back home.

Things to do in Bend

Parks Nature Museums

Side Trips

Sunriver, Dee Wright Observatory, Smith Rock State Park, McKenzie Pass-Santiam Pass loop
Highlights from your plan
Smith Rock State Park ©
Smith Rock State Park
High Desert Museum ©
High Desert Museum
McKenzie Pass-Santiam Pass loop ©
McKenzie Pass-Santiam Pass loop

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