12 days in Oregon Itinerary

12 days in Oregon Itinerary

Created using Inspirock Oregon travel planner

Make it your trip
Fly
1
Portland
— 2 nights
Fly
2
Bend
— 2 nights
Drive
3
Crater Lake National Park
— 2 nights
Drive
4
Newport
— 2 nights
Drive
5
Cannon Beach
— 2 nights
Fly

S M T W T F S
26
27
28
29
30
31
1
2
3
4
5
6
7
8

Portland

— 2 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.
On the 26th (Sun), look for gifts at Powell's City of Books, then admire the natural beauty at International Rose Test Garden, then walk around Camassia Natural Area, and finally admire the majestic nature at Silver Falls State Park. Get ready for a full day of sightseeing on the 27th (Mon): stroll through Columbia River Gorge National Scenic Area.

For photos, reviews, traveler tips, and more tourist information, refer to the Portland journey maker website.

Chicago to Portland is an approximately 6-hour flight. You can also drive; or take a train. Traveling from Chicago to Portland, you'll gain 2 hours due to the time zone difference. Traveling from Chicago in July, expect little chillier with lows of 59°F in Portland. You'll set off for Bend on the 28th (Tue).

Things to do in Portland

Parks · Nature · Wildlife · Shopping

Side Trips

Bend

— 2 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.
On the 28th (Tue), take a peaceful walk through Shevlin Park. Get ready for a full day of sightseeing on the next day: hike along Peterson Ridge Trail, take a stroll through City of Sisters, then view the masterpieces at The Art of Alfred A. Dolezal Gallery, and finally grab your bike and head to Deschutes River Trail.

To find traveler tips, ratings, photos, and other tourist information, use the Bend trip itinerary planner.

Fly from Portland to Bend in 2.5 hours. Alternatively, you can drive; or take a bus. Expect slightly colder evenings in Bend when traveling from Portland in July, with lows around 52°F. Cap off your sightseeing on the 30th (Thu) early enough to go by car to Crater Lake National Park.

Things to do in Bend

Outdoors · Trails · Parks · Classes

Side Trips

Crater Lake National Park

— 2 nights
Reaching a depth of 592 m (1,943 ft), Crater Lake is the deepest lake in the United States.
Kick off your visit on the 31st (Fri): stroll through Annie Creek Canyon, then trek along Pinnacles Trail, then trek along Castle Crest Wildflower Trail, and finally take your sightseeing to a higher altitude at Watchman Peak. Get ready for a full day of sightseeing on the next day: take in the dramatic scenery at National Creek Falls and then take in the dramatic scenery at Whitehorse Falls.

To find photos, more things to do, other places to visit, and tourist information, read our Crater Lake National Park trip builder site.

Traveling by car from Bend to Crater Lake National Park takes 2.5 hours. Alternatively, you can do a combination of bus and taxi. Expect a bit warmer temperatures when traveling from Bend in July; daily highs in Crater Lake National Park reach 94°F and lows reach 61°F. Finish your sightseeing early on the 1st (Sat) to allow enough time to drive to Newport.

Things to do in Crater Lake National Park

Parks · Outdoors · Trails · Nature

Side Trip

Newport

— 2 nights
A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
Start off your visit on the 2nd (Sun): pick up some local products at Newport Farmer's Market, stop by Oregon Oyster Farms, then tour the pleasant surroundings at Ocean to Bay Trail, and finally tour the pleasant surroundings at Drift Creek Falls Trail.

To see reviews, maps, more things to do, and tourist information, read our Newport attractions planner.

Traveling by car from Crater Lake National Park to Newport takes 5.5 hours. Alternatively, you can do a combination of flight and bus; or do a combination of taxi, train, and bus. When traveling from Crater Lake National Park in August, plan for colder days and little chillier nights in Newport: temperatures range from 64°F by day to 51°F at night. Wrap up your sightseeing by early afternoon on the 3rd (Mon) to allow time for the car ride to Cannon Beach.

Things to do in Newport

Outdoors · Parks · Trails · Beaches

Side Trip

Cannon Beach

— 2 nights
Cannon Beach is a city in Clatsop County, Oregon, United States. Kick off your visit on the 3rd (Mon): enjoy the sand and surf at Tolovana Beach State Recreation Site. On your second day here, tour the pleasant surroundings at Haystack Rock, then enjoy the sand and surf at Cannon Beach, and then tour the pleasant surroundings at Rockaway Beach Wayside.

For photos, reviews, maps, and tourist information, refer to the Cannon Beach tour planner.

Traveling by car from Newport to Cannon Beach takes 3 hours. Alternatively, you can take a bus. Traveling from Newport in August, you will find days in Cannon Beach are a bit warmer (71°F), and nights are about the same (55°F). Finish your sightseeing early on the 5th (Wed) to allow enough time to fly back home.

Things to do in Cannon Beach

Outdoors · Parks · Beaches · 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.