38 days in Oregon Itinerary

38 days in Oregon Itinerary

Created using Inspirock Oregon visit planner
Make it your trip
Fly
1
Portland
— 1 night
Drive
2
Drake Crossing
— 1 day
Drive
3
Blue River
— 2 nights
Drive
4
Bend
— 2 nights
Drive
5
Oakridge
— 3 nights
Drive
6
Crater Lake National Park
— 3 nights
Drive
7
Klamath Falls
— 2 nights
Drive
8
Medford
— 2 nights
Drive
9
Brookings
— 2 nights
Drive
10
Umpqua
— 1 night
Drive
11
Reedsport
— 1 night
Drive
12
Newport
— 2 nights
Drive
13
Salem
— 2 nights
Drive
14
Cannon Beach
— 3 nights
Drive
15
Seaside
— 2 nights
Drive
16
Astoria
Drive
17
Troutdale
— 1 night
Drive
18
Hood River
— 2 nights
Drive
19
The Dalles
— 2 nights
Drive
20
Timberline Lodge
— 3 nights
Drive
21
Portland
— 1 night
Fly

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Portland — 1 night

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.
Portland Japanese Garden has been added to your itinerary. On the 5th (Sun), admire the natural beauty at Portland Japanese Garden and then admire the natural beauty at International Rose Test Garden.

For ratings, where to stay, maps, and tourist information, read our Portland itinerary planning tool.

Kansas City to Portland is an approximately 5-hour flight. You can also drive; or take a bus. Traveling from Kansas City to Portland, you'll gain 2 hours due to the time zone difference. In September in Portland, expect temperatures between 76°F during the day and 55°F at night. Finish up your sightseeing early on the 6th (Mon) so you can go by car to Drake Crossing.
Parks

Drake Crossing — 1 day

On the 6th (Mon), immerse yourself in nature at Silver Falls State Park.

To see where to stay, reviews, photos, and tourist information, you can read our Drake Crossing online journey planner.

Traveling by car from Portland to Drake Crossing takes 1.5 hours. On the 6th (Mon), wrap the sightseeing up by early afternoon so you can drive to Blue River.
Parks · Nature

Blue River — 2 nights

Blue River is an unincorporated community in Lane County, Oregon, United States. Start off your visit on the 7th (Tue): admire the sheer force of Proxy Falls and then see the sky in a new way at Dee Wright Observatory.

To see where to stay, traveler tips, more things to do, and other tourist information, read Blue River vacation tool.

You can drive from Drake Crossing to Blue River in 2.5 hours. September in Blue River sees daily highs of 77°F and lows of 50°F at night. Finish your sightseeing early on the 8th (Wed) so you can drive to Bend.
Childrens Museums · Museums · Outdoors · Parks
Side Trip

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.
Your day by day itinerary now includes Cascade Lakes Welcome Station as well as Newberry National Volcanic Monument. On the 8th (Wed), trek along Pilot Butte State Scenic Viewpoint, get answers to all your questions at Cascade Lakes Welcome Station, and then hike along Falls Creek Trail to Green Lake. Keep things going the next day: admire the majestic nature at Smith Rock State Park and then pause for some photo ops at Newberry National Volcanic Monument.

To see more things to do, where to stay, maps, and more tourist information, read our Bend online tour planner.

You can drive from Blue River to Bend in 2 hours. Traveling from Blue River in September, expect little chillier with lows of 44°F in Bend. Wrap up your sightseeing on the 10th (Fri) to allow time to drive to Oakridge.
Parks · Outdoors · Trails · Nature
Side Trip

Oakridge — 3 nights

Oakridge is a city in Lane County, Oregon, United States. You'll find plenty of places to visit near Oakridge: Lowell Bridge (in Lowell) and Dexter Lake (in Dexter). There's lots more to do: admire the sheer force of Salt Creek Falls, look for gifts at Willamette Mountain Mercantile-Oakridge Bike Shop, stroll through Willamette Hatchery, and snap pictures at The Office Bridge.

To find where to stay, maps, and more tourist information, read our Oakridge trip planner.

Traveling by car from Bend to Oakridge takes 2 hours. Traveling from Bend in September, plan for somewhat warmer nights in Oakridge, with lows around 50°F. Wrap up your sightseeing on the 13th (Mon) early enough to drive to Crater Lake National Park.
Parks · Nature · Historic Sites · Scenic Drive
Side Trips

Crater Lake National Park — 3 nights

Reaching a depth of 592 m (1,943 ft), Crater Lake is the deepest lake in the United States.
Your day by day itinerary now includes Toketee Falls, Rim Village Visitor Center, Pinnacles Overlook Hike, and other attractions you added. Next up on the itinerary: take a memorable drive along Rim Dr.

For traveler tips, photos, more things to do, and tourist information, read Crater Lake National Park day trip website.

Traveling by car from Oakridge to Crater Lake National Park takes 2.5 hours. Traveling from Oakridge in September, expect nights in Crater Lake National Park to be about the same, around 53°F, while days are a bit warmer, around 83°F. You'll set off for Klamath Falls on the 16th (Thu).
Outdoors · Parks · Nature · Scenic Drive

Klamath Falls — 2 nights

Klamath Falls is a city in and the county seat of Klamath County, Oregon, United States. On the 17th (Fri), let little ones run wild at Moore Park and then play a few rounds at Running Y Ranch Golf Course. Keep things going the next day: examine the collection at The Favell Museum Native American Artifacts and Contemporary Western Art and then take an in-depth tour of Klamath County Museum.

For reviews, where to stay, traveler tips, and more tourist information, you can read our Klamath Falls road trip planner.

Drive from Crater Lake National Park to Klamath Falls in 1.5 hours. Prepare for slightly colder weather when traveling from Crater Lake National Park in September: high temperatures in Klamath Falls hover around 76°F and lows are around 40°F. Finish up your sightseeing early on the 18th (Sat) so you can go by car to Medford.
Museums · Outdoors · Fun & Games · Parks

Medford — 2 nights

Medford is a city in, and county seat of, Jackson County, Oregon, United States. Start off your visit on the 19th (Sun): relax and float downstream with a rafting and tubing tour, do a tasting at Grizzly Peak Winery, and then see a show at Oregon Shakespeare Festival. On your second day here, stroll through Natural Bridge Loop and then explore the activities along Rogue River.

To see reviews, other places to visit, more things to do, and tourist information, go to the Medford travel route planner.

Drive from Klamath Falls to Medford in 2 hours. Plan for somewhat warmer temperatures traveling from Klamath Falls in September, with highs in Medford at 83°F and lows at 53°F. Finish your sightseeing early on the 20th (Mon) so you can travel to Brookings.
Outdoors · Parks · Adventure · Tours
Side Trip

Brookings — 2 nights

Brookings is a city in Curry County, Oregon, United States. Kick off your visit on the 21st (Tue): immerse yourself in nature at Harris Beach State Park and then kick back and relax at Lone Ranch Beach. On your second day here, don't miss a visit to Rogue River Bridge, then take a tour of The Mary D Hume, and then explore and take pictures at Samuel H. Boardman State Scenic Corridor.

For more things to do, reviews, photos, and other tourist information, refer to the Brookings day trip planner.

You can drive from Medford to Brookings in 3 hours. When traveling from Medford in September, plan for a bit cooler days and about the same nights in Brookings: temperatures range from 69°F by day to 53°F at night. Finish your sightseeing early on the 22nd (Wed) so you can travel to Umpqua.
Outdoors · Parks · Scenic Drive · Beaches
Side Trip

Umpqua — 1 night

Umpqua is an unincorporated community in Douglas County, in the U.S. state of Oregon. Start off your visit on the 23rd (Thu): learn about winemaking at Henry Estate Winery and then snap pictures at Rochester Covered Bridge.

To find where to stay, more things to do, traveler tips, and other tourist information, refer to the Umpqua online travel planner.

Traveling by car from Brookings to Umpqua takes 3.5 hours. When traveling from Brookings in September, plan for somewhat warmer days in Umpqua, with highs around 80°F, while nights are about the same with lows around 54°F. Finish up your sightseeing early on the 23rd (Thu) so you can travel to Reedsport.
Wineries
Side Trip

Reedsport — 1 night

Reedsport is a city in Douglas County, Oregon, United States. Kick off your visit on the 24th (Fri): explore the striking landscape of Oregon Dunes National Recreation Area.

For other places to visit, where to stay, photos, and other tourist information, go to the Reedsport day trip planner.

Getting from Umpqua to Reedsport by car takes about 1.5 hours. When traveling from Umpqua in September, plan for slightly colder days in Reedsport, with highs around 68°F, while nights are about the same with lows around 52°F. Finish up your sightseeing early on the 24th (Fri) so you can go by car to Newport.
Parks · Nature

Newport — 2 nights

A town that survives on the sea, Newport's population of just over 10,000 supports a healthy commercial fishing industry.
Your day by day itinerary now includes Yaquina Head Lighthouse. On the 25th (Sat), enjoy the sea views from Yaquina Head Lighthouse, stroll through Cape Perpetua Visitor Center - Siuslaw National Forest, and then visit a coastal fixture at Heceta Head Lighthouse. Get ready for a full day of sightseeing on the 26th (Sun): observe the fascinating underwater world at Oregon Coast Aquarium, then see majestic marine mammals with Marine Discovery Tours, and then take a leisurely stroll along Newport's Historic Bayfront.

To find traveler tips, photos, and more tourist information, you can read our Newport online tour itinerary planner.

Traveling by car from Reedsport to Newport takes 2 hours. In September in Newport, expect temperatures between 64°F during the day and 50°F at night. Finish your sightseeing early on the 26th (Sun) to allow enough time to drive to Salem.
Historic Sites · Parks · Outdoors · Scenic Drive
Side Trips

Salem — 2 nights

Salem is the capital of the U.S. state of Oregon, and the county seat of Marion County. On the 27th (Mon), get a sense of history and politics at Oregon State Capitol and then examine the collection at Evergreen Aviation & Space Museum. Get ready for a full day of sightseeing on the next day: indulge your senses at Cellar Door Wine Tours.

To find reviews, more things to do, ratings, and tourist information, read our Salem trip planner.

Traveling by car from Newport to Salem takes 2 hours. Alternatively, you can take a bus. Expect somewhat warmer weather when traveling from Newport in September: highs in Salem hover around 77°F, while lows dip to 52°F. Cap off your sightseeing on the 28th (Tue) early enough to go by car to Cannon Beach.
Tours · Wineries · Museums
Side Trips

Cannon Beach — 3 nights

Cannon Beach is a city in Clatsop County, Oregon, United States. Cannon Beach is known for nature, beaches, and museums. Your trip includes some of its best attractions: explore the striking landscape at Haystack Rock, immerse yourself in nature at Ecola State Park, kick back and relax at Cannon Beach, and tour the pleasant surroundings at Manzanita Beach.

For photos, other places to visit, and more tourist information, read Cannon Beach road trip website.

You can drive from Salem to Cannon Beach in 2.5 hours. Alternatively, you can take a bus; or do a combination of train and bus. When traveling from Salem in September, plan for a bit cooler days and about the same nights in Cannon Beach: temperatures range from 69°F by day to 52°F at night. Cap off your sightseeing on the 1st (Fri) early enough to go by car to Seaside.
Parks · Nature · Outdoors · Beaches
Side Trip

Seaside — 2 nights

Seaside is a city in Clatsop County, Oregon, United States. Kick off your visit on the 2nd (Sat): appreciate the history behind Seaside Beach Lewis and Clark Monument, then make a trip to Turnaround at Seaside, and then get up close and personal with brilliant marine life at Seaside Aquarium.

For where to stay, other places to visit, traveler tips, and more tourist information, refer to the Seaside vacation planning website.

Seaside is just a short distance from Cannon Beach. In October, plan for daily highs up to 63°F, and evening lows to 48°F. Finish your sightseeing early on the 3rd (Sun) so you can drive to Astoria.
Zoos & Aquariums · Parks

Astoria

Astoria, named for famed fur trader John Jacob Astor, resides near the mouth of the Columbia River.
To see traveler tips, maps, ratings, and other tourist information, use the Astoria itinerary planning site.

Astoria is just a stone's throw from Seaside. In October, daily temperatures in Astoria can reach 63°F, while at night they dip to 48°F. On the 3rd (Sun), you're off to Troutdale.
Parks · Outdoors · Shopping · Museums

Troutdale — 1 night

Troutdale is a city in Multnomah County, Oregon, U.S.A., north of Gresham and east of Wood Village. Start off your visit on the 3rd (Sun): admire the landmark architecture of Vista House and then steep yourself in history at Columbia River Highway. On the 4th (Mon), you'll have a packed day of sightseeing: take in the dramatic scenery at Multnomah Falls and then admire the engineering at Bonneville Lock & Dam.

For maps, photos, other places to visit, and other tourist information, go to the Troutdale trip itinerary tool.

Traveling by car from Astoria to Troutdale takes 2 hours. In October, daytime highs in Troutdale are 66°F, while nighttime lows are 48°F. Cap off your sightseeing on the 4th (Mon) early enough to go by car to Hood River.
Parks · Historic Sites · Nature
Side Trips

Hood River — 2 nights

The city of Hood River is the seat of Hood River County, Oregon, United States. Your day by day itinerary now includes Tamanawas Falls Trail, Timberline Lodge and Ski Area and The Gorge White House. Kick off your visit on the 5th (Tue): fly down the slopes at Timberline Lodge and Ski Area and then relax in the rural setting at The Gorge White House. Keep things going the next day: contemplate the geological forces at Mount Hood and then take in the dramatic scenery at Tamanawas Falls Trail.

To see ratings, reviews, where to stay, and more tourist information, refer to the Hood River trip maker tool.

Drive from Troutdale to Hood River in an hour. In October, daily temperatures in Hood River can reach 67°F, while at night they dip to 45°F. Finish your sightseeing early on the 6th (Wed) so you can drive to The Dalles.
Nature · Winter Sports · Parks · Historic Sites
Side Trip

The Dalles — 2 nights

The Dalles is the county seat and largest city of Wasco County, Oregon, United States. Your day by day itinerary now includes Mount Hood Railroad as well as Historic Columbia River Highway State Trail. On the 7th (Thu), get interesting insight from Mount Hood Railroad, trek along Historic Columbia River Highway State Trail, then get engrossed in the history at Fort Dalles Museum and Anderson Homestead, then see the interesting displays at Columbia Gorge Discovery Center & Museum, and finally examine the collection at Fire Museum in City Hall. On your second day here, contemplate the long history of Maryhill Museum of Art, pause for some photo ops at Stonehenge Memorial, and then examine the collection at Western Antique Aeroplane & Automobile Museum.

For reviews, traveler tips, more things to do, and tourist information, you can read our The Dalles visit planner.

The Dalles is just a short distance from Hood River. In October, plan for daily highs up to 67°F, and evening lows to 45°F. Finish your sightseeing early on the 8th (Fri) so you can drive to Timberline Lodge.
Museums · Historic Sites · Outdoors · Parks
Side Trips

Timberline Lodge — 3 nights

Perched high on the south face of one of the most iconic peaks in the Pacific Northwest, Timberline Lodge is the ski and snowboarding area known for the eponymous historic lodge, the design of which emphasizes the area's natural beauty.
Your day by day itinerary now includes Trillium Lake as well as Punchbowl Falls. On the 9th (Sat), take in the dramatic scenery at Punchbowl Falls, explore the activities along Trillium Lake, hike along Ramona Falls Trail, then delve into the lush surroundings at Mt. Hood National Forest, and finally hit the slopes at Timberline Lodge and Ski Area. On the 10th (Sun), you'll have a packed day of sightseeing: experience rural life at Kiyokawa Family Orchards.

For where to stay, maps, photos, and more tourist information, read Timberline Lodge day trip planning site.

Getting from The Dalles to Timberline Lodge by car takes about 1.5 hours. October in Timberline Lodge sees daily highs of 67°F and lows of 45°F at night. On the 11th (Mon), wrap the sightseeing up by early afternoon so you can drive to Portland.
Nature · Parks · Historic Sites · Winter Sports
Side Trips

Portland — 1 night

Your day by day itinerary now includes Portland Japanese Garden. Start off your visit on the 11th (Mon): examine the collection at Oregon Museum of Science and Industry, admire the natural beauty at Portland Japanese Garden, then admire the natural beauty at Hoyt Arboretum, and finally delve into the lush surroundings at The Grotto - National Sanctuary of Our Sorrowful Mother.

To see other places to visit, traveler tips, maps, and tourist information, read our Portland sightseeing planner.

Traveling by car from Timberline Lodge to Portland takes 1.5 hours. You will have some time to spend on the 12th (Tue) before leaving for home.
Parks · Historic Sites · Nature · Wildlife

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.