14 days in Oregon Itinerary

14 days in Oregon Itinerary

Created using Inspirock Oregon travel route planner

©
Make it your trip
Fly
1
Bend
— 2 nights
Drive
2
Crater Lake National Park
— 2 nights
Drive
3
Brookings
— 2 nights
Drive
4
Newport
— 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.
Kick off your visit on the 30th (Thu): take a memorable drive along McKenzie Pass-Santiam Pass loop, then explore the activities along Deschutes River, and then relax and float downstream with a rafting and tubing tour. Keep things going the next day: delve into the lush surroundings at Deschutes National Forest, then immerse yourself in nature at Smith Rock State Park, and then hike along Pilot Butte State Scenic Viewpoint.

For photos, ratings, more things to do, and more tourist information, you can read our Bend trip itinerary planning site.

Milwaukee to Bend is an approximately 9.5-hour flight. You can also drive; or do a combination of train and bus. Traveling from Milwaukee to Bend, you'll gain 2 hours due to the time zone difference. Traveling from Milwaukee in July, Bend is a bit cooler at night with lows of 52°F. Wrap up your sightseeing on the 31st (Fri) to allow time to drive to Crater Lake National Park.

Things to do in Bend

Parks · Nature · Outdoors · Trails

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 1st (Sat): take a memorable drive along Rim Dr and then explore the striking landscape of Crater Lake National Park. Keep things going the next day: look for all kinds of wild species at Rogue River Gorge Viewpoint, step off the mainland to explore Wizard Island, then trek along Cleetwood Cove Trail, and finally trek along Watchman Peak.

Ask Inspirock to suggest an itinerary and make planning a trip to Crater Lake National Park fast, fun, and easy.

You can drive from Bend to Crater Lake National Park in 2.5 hours. Another option is to do a combination of bus and taxi. Plan for a bit warmer temperatures traveling from Bend in July, with highs in Crater Lake National Park at 94°F and lows at 61°F. Wrap up your sightseeing on the 2nd (Sun) early enough to travel to Brookings.

Things to do in Crater Lake National Park

Parks · Nature · Outdoors · Trails

Side Trip

Brookings

— 2 nights
Brookings is a city in Curry County, Oregon, United States. Start off your visit on the 3rd (Mon): cruise along Samuel H. Boardman State Scenic Corridor, enjoy the sand and surf at Myers Creek Beach, and then step aboard The Mary D Hume. Keep things going the next day: immerse yourself in nature at Harris Beach State Park, enjoy the sand and surf at Lone Ranch Beach, then admire the majestic nature at Crissey Field State Park, and finally hike along Oregon Redwood Trail.

For maps, where to stay, and tourist information, refer to the Brookings trip planner.

Getting from Crater Lake National Park to Brookings by car takes about 4 hours. Traveling from Crater Lake National Park in August, you will find days in Brookings are much colder (68°F), and nights are little chillier (53°F). Finish up your sightseeing early on the 4th (Tue) so you can travel to Newport.

Things to do in Brookings

Parks · Outdoors · Beaches · Nature

Side Trips

Newport

— 2 nights
A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
Kick off your visit on the 5th (Wed): look for all kinds of wild species at Fogarty Creek State Recreation Area, then enjoy the sea views from Yaquina Head Lighthouse, then look for all kinds of wild species at Yaquina Head Outstanding Natural Area, and finally explore the wealth of natural beauty at Mike Miller Park. Get ready for a full day of sightseeing on the 6th (Thu): cruise along Cape Perpetua Visitor Center - Siuslaw National Forest, visit a coastal fixture at Heceta Head Lighthouse, and then take in the waterfront at Yachats coastline.

To see where to stay, more things to do, reviews, and tourist information, read our Newport trip itinerary maker website.

Traveling by car from Brookings to Newport takes 4.5 hours. August in Newport sees daily highs of 64°F and lows of 51°F at night. Wrap up your sightseeing on the 6th (Thu) to allow time to drive to Cannon Beach.

Things to do in Newport

Parks · Wildlife · Nature · Historic Sites

Side Trips

Cannon Beach

— 2 nights
Cannon Beach is a city in Clatsop County, Oregon, United States. Kick off your visit on the 7th (Fri): kick back and relax at Cannon Beach, explore the striking landscape at Haystack Rock, then view the masterpieces at Bronze Coast Gallery, and finally immerse yourself in nature at Ecola State Park. Here are some ideas for day two: stroll through Hug Point State Recreation Site, then immerse yourself in nature at Oswald West State Park, and then admire the majestic nature at Hug Point State Park.

For reviews, more things to do, maps, and other tourist information, go to the Cannon Beach online journey planner.

You can drive from Newport to Cannon Beach in 3 hours. Another option is to take a bus. When traveling from Newport in August, plan for a bit warmer days in Cannon Beach, with highs around 71°F, while nights are about the same with lows around 55°F. Wrap up your sightseeing on the 8th (Sat) to allow time to travel to Troutdale.

Things to do in Cannon Beach

Parks · Nature · Beaches · Outdoors

Side Trip

Troutdale

— 3 nights
Troutdale is a city in Multnomah County, Oregon, U.S.A., north of Gresham and east of Wood Village. Kick off your visit on the 9th (Sun): make a trip to Jonsrud Viewpoint, look for all kinds of wild species at Bonneville Hatchery, then take in the dramatic natural features at Oneonta Gorge, and finally take in the dramatic scenery at Multnomah Falls. On the 10th (Mon), you'll have a packed day of sightseeing: look for all kinds of wild species at Wildwood Recreation Site, then fly down the slopes at Timberline Lodge and Ski Area, and then take in the dramatic scenery at Little Zigzag Falls.

For traveler tips, where to stay, other places to visit, and other tourist information, read Troutdale holiday maker tool.

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 by early afternoon on the 11th (Tue) to allow enough time to travel back home.

Things to do in Troutdale

Parks · Nature · Wildlife · 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.