21 days in Oregon Itinerary

21 days in Oregon Itinerary

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Route & dates

21 days in Oregon Itinerary

Start: New York City
foot + Fly:  9​h
1
Portland
— 3 nights
bus:  1​h 15​min
2
Hood River
— 2 nights
Drive:  30​min
3
Cascade Locks
— 1 night
Drive:  1​h 15​min
4
Government Camp
— 2 nights
Drive:  2​h 30​min
5
Bend
— 2 nights
Drive:  2​h 45​min
6
Crater Lake National Park
— 2 nights
Drive:  2​h
7
Grants Pass
— 2 nights
Drive:  3​h
8
Florence
— 1 night
Drive:  4​h
9
Cannon Beach
— 3 nights
Drive:  1​h 30​min
10
Portland
— 2 nights
Fly + foot:  9​h
End: New York City

3
nights
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.
On the 20th (Tue), get a sense of history and politics at Portland City Hall, then indulge your senses at some of the top wineries in the area, and then see the interesting displays at Oregon Museum of Science and Industry. Here are some ideas for day two: test your problem-solving skills at popular escape rooms, then learn about wildlife with up-close encounters at Washington Park, then steep yourself in history at Pittock Mansion, and finally hike along Forest Park.

For photos, where to stay, other places to visit, and tourist information, read Portland trip builder tool .

New York City to Portland is an approximately 9-hour flight. You can also fly; or drive. The time zone difference when traveling from New York City to Portland is minus 3 hours. Expect slightly colder evenings in Portland when traveling from New York City in August, with lows around 60°F. On the 22nd (Thu), you'll have the morning to explore before heading off to Hood River.

Things to do in Portland

Tours Parks Museums
Highlights from your plan
Room Escape Games
Forest Park ©
Forest Park
Oregon Museum of Science and Industry ©

2
nights
Hood River

Hood River ©
The city of Hood River is the seat of Hood River County, Oregon, United States. On the 22nd (Thu), get outside with Big Winds and then trek along Horsetail Falls- Columbia River Gorge. On your second day here, examine the collection at Western Antique Aeroplane & Automobile Museum, get a taste of the local shopping with Hood River Lavender, and then tour the pleasant surroundings at Mount Hood.

To see more things to do, ratings, and more tourist information, read our Hood River tour itinerary planner .

Getting from Portland to Hood River by bus takes about 1.5 hours. Other options: drive; or take a train. Expect a daytime high around 81°F in August, and nighttime lows around 60°F. Finish up your sightseeing early on the 24th (Sat) so you can go by car to Cascade Locks.

Things to do in Hood River

Outdoors Parks Nature
Highlights from your plan
Mount Hood ©
Mount Hood
Big Winds ©
Big Winds

1
night
Cascade Locks

Cascade Locks ©
Cascade Locks is a city in Hood River County, Oregon, United States. On the 24th (Sat), admire the sheer force of Multnomah Falls, then take in the dramatic natural features at Oneonta Gorge, then see human ingenuity at work at Bonneville Lock & Dam, and finally admire the sheer force of Starvation Creek State Park. Here are some ideas for day two: take a memorable drive along Cape Horn Lookout, then identify plant and animal life at Bonneville Hatchery, then snap pictures at Bridge of the Gods, and finally explore and take pictures at Sturgeon Viewing Pond and Interpretive Center.

For ratings, maps, more things to do, and tourist information, read Cascade Locks travel route planner .

Cascade Locks is just a stone's throw from Hood River. Expect a daytime high around 81°F in August, and nighttime lows around 60°F. Finish up your sightseeing early on the 25th (Sun) so you can go by car to Government Camp.

Things to do in Cascade Locks

Parks Nature Outdoors

Side Trips

Multnomah Falls, Cape Horn Lookout
Highlights from your plan
Oneonta Gorge ©
Oneonta Gorge
Multnomah Falls ©
Multnomah Falls
Starvation Creek State Park ©
Starvation Creek State Park

2
nights
Government Camp

Government Camp ©
Government Camp is an unincorporated community and census-designated place located in Clackamas County, Oregon, United States, south of Mount Hood and north of Tom Dick and Harry Mountain. On the 26th (Mon), explore the activities along Trillium Lake, hike along Little Zigzag Falls, and then contemplate the long history of Timberline Lodge and Ski Area. Get ready for a full day of sightseeing on the next day: relax and float downstream with a rafting and tubing tour.

For more things to do, photos, traveler tips, and more tourist information, go to the Government Camp sightseeing site .

Drive from Cascade Locks to Government Camp in 1.5 hours. In August, daily temperatures in Government Camp can reach 81°F, while at night they dip to 60°F. Wrap up your sightseeing on the 27th (Tue) early enough to travel to Bend.

Things to do in Government Camp

Nature Outdoors Parks

Side Trips

Timberline Lodge and Ski Area, River Rafting & Tubing
Highlights from your plan
Trillium Lake ©
Trillium Lake
Timberline Lodge and Ski Area ©
Timberline Lodge and Ski Area
River Rafting & Tubing

2
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.
On the 27th (Tue), take in the dramatic natural features at Balancing Rocks. Here are some ideas for day two: admire the majestic nature at Smith Rock State Park, walk around Drake Park, and then let the river carry you with a rafting and tubing tour.

To see other places to visit, photos, ratings, and more tourist information, read Bend trip itinerary tool .

Getting from Government Camp to Bend by car takes about 2.5 hours. Traveling from Government Camp in August, plan for little chillier nights in Bend, with lows around 52°F. Wrap up your sightseeing on the 29th (Thu) early enough to drive to Crater Lake National Park.

Things to do in Bend

Parks Nature Wildlife

Side Trip

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

2
nights
Crater Lake National Park

Crater Lake National Park ©
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 30th (Fri): take a memorable drive along Rim Dr and then explore the wealth of natural beauty at Crater Lake National Park. Here are some ideas for day two: steep yourself in history at Rim Village Visitor Center, hike along Cleetwood Cove Trail, and then head off the coast to Wizard Island.

To find other places to visit, maps, reviews, and tourist information, use the Crater Lake National Park trip planner.

You can drive from Bend to Crater Lake National Park in 3 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. Wrap up your sightseeing on the 31st (Sat) to allow time to drive to Grants Pass.

Things to do in Crater Lake National Park

Parks Nature Outdoors
Highlights from your plan
Crater Lake National Park ©
Crater Lake National Park
Rim Dr ©
Rim Dr
Cleetwood Cove Trail ©
Cleetwood Cove Trail

2
nights
Grants Pass

Grants Pass ©
Grants Pass is a city in, and the county seat of, Josephine County, Oregon, United States. Start off your visit on the 1st (Sun): see the interesting displays at Bear Hotel Artworks Museum, explore the activities along Rogue River, experience rural life at Rogue Creamery Dairy Farm, then identify plant and animal life at Wildlife Images - Rehabilitation & Education Center, and finally get a taste of the local shopping with The Glass Forge. Get ready for a full day of sightseeing on the 2nd (Mon): do a tasting at Wooldridge Creek Winery, trek along Natural Bridge Loop, and then explore the striking landscape at Upper and Lower Table Rock.

To see ratings, traveler tips, reviews, and other tourist information, refer to the Grants Pass trip maker .

Traveling by car from Crater Lake National Park to Grants Pass takes 2 hours. When traveling from Crater Lake National Park in August, plan for little chillier days and about the same nights in Grants Pass: temperatures range from 78°F by day to 57°F at night. Cap off your sightseeing on the 2nd (Mon) early enough to travel to Florence.

Things to do in Grants Pass

Parks Nature Trails

Side Trip

Medford
Highlights from your plan
Upper and Lower Table Rock ©
Upper and Lower Table Rock
Wooldridge Creek Winery ©
Wooldridge Creek Winery

1
night
Florence

Florence ©
Florence is a coastal city in Lane County, in the U.S. Start off your visit on the 3rd (Tue): take a memorable drive along Cape Perpetua Visitor Center - Siuslaw National Forest, then explore the fascinating underground world of Sea Lion Caves, and then putt your heart out at Sandland Adventures.

To see more things to do, ratings, other places to visit, and tourist information, read our Florence travel planner.

Traveling by car from Grants Pass to Florence takes 3 hours. In September in Florence, expect temperatures between 68°F during the day and 52°F at night. Finish your sightseeing early on the 3rd (Tue) so you can drive to Cannon Beach.

Things to do in Florence

Nature Parks Scenic Drive

Side Trip

Cape Perpetua Visitor Center - Siuslaw National Forest
Highlights from your plan
Sandland Adventures ©
Sandland Adventures
Sea Lion Caves ©
Sea Lion Caves

3
nights
Cannon Beach

Cannon Beach ©
Cannon Beach is a city in Clatsop County, Oregon, United States. On the 4th (Wed), immerse yourself in nature at Hug Point State Park, then tour the pleasant surroundings at Haystack Rock, and then tour the pleasant surroundings at Cannon Beach. On the 5th (Thu), you'll have a packed day of sightseeing: admire the majestic nature at Oswald West State Park, immerse yourself in nature at Ecola State Park, then stop by Seaside Candyman, and finally pause for some photo ops at Astoria Column.

To see more things to do, maps, photos, and more tourist information, you can read our Cannon Beach travel itinerary planner .

Drive from Florence to Cannon Beach in 4 hours. Alternatively, you can do a combination of bus and flight; or take a bus. September in Cannon Beach sees daily highs of 69°F and lows of 52°F at night. Finish your sightseeing early on the 6th (Fri) so you can drive to Portland.

Things to do in Cannon Beach

Parks Nature Beaches

Side Trips

Seaside Candyman, Astoria Column
Highlights from your plan
Cannon Beach ©
Cannon Beach
Ecola State Park ©
Ecola State Park
Oswald West State Park ©
Oswald West State Park

2
nights
Portland

Portland ©
Start off your visit on the 6th (Fri): take in nature's colorful creations at Portland Japanese Garden, admire the natural beauty at International Rose Test Garden, then learn about wildlife with up-close encounters at Oregon Zoo, then look for gifts at Powell's City of Books, and finally take in nature's colorful creations at Lan Su Chinese Garden. Get ready for a full day of sightseeing on the next day: contemplate the long history of Pittock Mansion, indulge your senses at some of the top wineries in the area, and then stroll around Laurelhurst Park.

To find maps, photos, ratings, and more tourist information, go to the Portland day trip tool .

You can drive from Cannon Beach to Portland in 1.5 hours. Alternatively, you can take a bus. When traveling from Cannon Beach in September, plan for somewhat warmer days in Portland, with highs around 76°F, while nights are about the same with lows around 55°F. On the 8th (Sun), you'll have the morning to explore before heading back home.

Things to do in Portland

Parks Tours Zoos & Aquariums
Highlights from your plan
Portland Japanese Garden ©
Portland Japanese Garden
Powell's City of Books ©
Powell's City of Books
Oregon Zoo ©
Oregon Zoo

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