14 days in Oregon Itinerary

14 days in Oregon Itinerary

Created using Inspirock Oregon tour itinerary maker

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Make it your trip
Fly
1
Bend
— 2 nights
Drive
2
Crater Lake National Park
— 1 night
Drive
3
Brookings
— 2 nights
Drive
4
Yachats
— 2 nights
Drive
5
Cannon Beach
— 2 nights
Drive
6
Troutdale
— 3 nights
+2
Drive to Seattle Tacoma International Airport, Fly to Chicago O'Hare International Airport, Drive to Milwaukee

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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.
Start off your visit on the 30th (Thu): stroll around Drake Park, let the river carry you with a rafting and tubing tour, and then contemplate the waterfront views at Deschutes River. Here are some ideas for day two: explore the fascinating underground world of Lava River Cave, contemplate the geological forces at Newberry National Volcanic Monument, and then admire the sheer force of Tumalo Falls.

To see traveler tips, more things to do, maps, and more tourist information, read our Bend driving holiday website.

Milwaukee to Bend is an approximately 9.5-hour flight. You can also drive; or do a combination of train and bus. Due to the time zone difference, you'll gain 2 hours traveling from Milwaukee to Bend. Traveling from Milwaukee in July, you can expect nighttime temperatures to be slightly colder in Bend, with lows of 52°F. You will leave for Crater Lake National Park on the 1st (Sat).

Things to do in Bend

Parks · Nature · Outdoors · Tours

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.
Kick off your visit on the 1st (Sat): contemplate the long history of Rim Village Visitor Center and then cruise along Rim Dr.

For photos, reviews, ratings, and tourist information, refer to the Crater Lake National Park road trip 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. Traveling from Bend in August, things will get a bit warmer in Crater Lake National Park: highs are around 93°F and lows about 60°F. Finish up your sightseeing early on the 2nd (Sun) so you can travel to Brookings.

Things to do in Crater Lake National Park

Scenic Drive · Outdoors · Historic Sites

Brookings

— 2 nights
Brookings is a city in Curry County, Oregon, United States. Kick off your visit on the 2nd (Sun): enjoy the sand and surf at Ophir Beach, stroll through Myers Creek Beach, and then kick back and relax at Lone Ranch Beach. Keep things going the next day: immerse yourself in nature at Harris Beach State Park, then cruise along Samuel H. Boardman State Scenic Corridor, and then trek along Oregon Redwood Trail.

To see other places to visit, traveler tips, maps, and tourist information, use the Brookings trip planner.

Getting from Crater Lake National Park to Brookings by car takes about 4 hours. When traveling from Crater Lake National Park in August, plan for colder days and little chillier nights in Brookings: temperatures range from 68°F by day to 53°F at night. Cap off your sightseeing on the 4th (Tue) early enough to travel to Yachats.

Things to do in Brookings

Outdoors · Parks · Beaches · Scenic Drive

Side Trips

Yachats

— 2 nights
Yachats is a small coastal city in Lincoln County, Oregon, United States. Start off your visit on the 4th (Tue): cruise along Cape Perpetua Visitor Center - Siuslaw National Forest, then take in the dramatic natural features at Thor's Well, then explore the striking landscape at Devil's Churn, and finally take in the waterfront at Yachats coastline. On your second day here, catch some excitement at Sandland Adventures, then kick back and relax at Heceta Beach, then enjoy the sea views from Heceta Head Lighthouse, and finally admire the majestic nature at Smelt Sands State Park.

To find more things to do, maps, photos, and other tourist information, read Yachats trip itinerary website.

Drive from Brookings to Yachats in 4 hours. In August, daily temperatures in Yachats can reach 64°F, while at night they dip to 51°F. Finish up your sightseeing early on the 6th (Thu) so you can go by car to Cannon Beach.

Things to do in Yachats

Parks · Outdoors · Nature · Scenic Drive

Side Trip

Cannon Beach

— 2 nights
Cannon Beach is a city in Clatsop County, Oregon, United States. On the 6th (Thu), admire the majestic nature at Hug Point State Park, then stroll through Haystack Rock, and then kick back and relax at Cannon Beach. Here are some ideas for day two: tour the pleasant surroundings at Manzanita Beach, admire the majestic nature at Oswald West State Park, and then identify plant and animal life at Hug Point State Recreation Site.

To find out how to plan a trip to Cannon Beach, use our trip itinerary maker.

Getting from Yachats to Cannon Beach by car takes about 3.5 hours. Other options: fly; or take a bus. When traveling from Yachats in August, plan for a bit warmer days and about the same nights in Cannon Beach: temperatures range from 71°F by day to 55°F at night. Wrap up your sightseeing on the 8th (Sat) early enough to travel to Troutdale.

Things to do in Cannon Beach

Parks · Beaches · Outdoors · Nature

Side Trips

Troutdale

— 3 nights
Troutdale is a city in Multnomah County, Oregon, U.S.A., north of Gresham and east of Wood Village. Timberline Lodge and Ski Area and Columbia River Highway will appeal to history buffs. You'll visit kid-friendly attractions like Little Zigzag Falls and Mt. Hood Adventure Park at Skibowl. Go for a jaunt from Troutdale to Cascade Locks to see Bonneville Lock & Dam about 30 minutes away. There's still lots to do: admire the sheer force of Multnomah Falls, take some stellar pictures from Cape Horn Overlook, delve into the lush surroundings at Mt. Hood National Forest, and immerse yourself in nature at Shepperd's Dell State Natural Area.

For maps, photos, where to stay, and more tourist information, go to the Troutdale day trip planning app.

You can drive from Cannon Beach to Troutdale in 2 hours. Traveling from Cannon Beach in August, you will find days in Troutdale are a bit warmer (85°F), and nights are about the same (58°F). Wrap up your sightseeing on the 11th (Tue) early enough to travel back home.

Things to do in Troutdale

Parks · Nature · Outdoors · Historic Sites

Side Trips

Oregon travel guide

4.5
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.